Substituted pyrrole carboxamides, processes for their preparation and their use as kinase inhibitors

Abstract

The present application relates to substituted pyrrole carboxamide derivatives of Formula (I) that modulate the activity of the cell division cycle 7-related kinase (Cdc7). Accordingly, the compounds of the present application are useful in the treatment of diseases associated with dysregulated kinase activity, such as cancer, cell proliferative disorders, viral infections, immune disorders, neurodegenerative disorders, cardiovascular diseases, and bone-related diseases. The present application also provides methods for making these compounds, pharmaceutical compositions comprising these compounds, and their medical uses.

Description

[0001] This invention relates to certain substituted pyrrole compounds that regulate protein kinase activity. Therefore, the compounds of this invention can be used to treat diseases associated with dysregulated kinase activity, such as cancer, cell proliferation disorders, viral infections, immune disorders, neurodegenerative diseases, cardiovascular diseases, and bone-related diseases.

[0002] The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods for treating diseases using pharmaceutical compositions comprising these compounds. Background of the Invention Dysfunction of protein kinases (PKs) is a hallmark of many diseases. Most oncogenes and proto-oncogenes involved in human cancers encode PKs. Enhanced PK activity is also associated with many non-malignant diseases. For general references on PK dysfunction or dysregulation, see, for example, Current Opinion in Chemical Biology 1999, 3 , 459-465.

[0004] Among the several protein kinases known in the art, the one associated with cancer cell growth is cell cycle 7-related protein kinase (Cdc7), a key cell cycle protein required for DNA replication by catalyzing the activation of MCM helicase at the DNA replication origin. Cdc7 kinase and its regulatory subunit Dbf4 are overexpressed in many tumors, and overexpression is associated with poor prognosis and advanced tumor grading. Cdc7 is also involved in mediating the handling of stalled replication forks after replication stress or damage has been resolved, and in DNA repair across damage (see Montagnoli A. et al.). EMBO Journal , 2002, p. 21 Volume, Issue 12, 3171; Montagnoli A. et al. Cancer Research 2004, p. 64 Volume, October 1, 7110; Hou Y. et al. Mol Oncol 2012, p. 29 Volume 3498; Day TA et al., 2010, J Cell Biol, Volume 191, 953).

[0005] Pyrrole carboxamide derivatives are known in the art as protein kinase inhibitors. Among pyrrole carboxamide derivatives, for example, WO2009 / 040399 reports that pyrimidinyl-pyrrole derivatives can be used in therapies for diseases related to dysregulated protein kinase activity, particularly the Polo-like kinase (PLK) family; WO2013 / 014039 and WO2014 / 019908 disclose pyrimidinyl-pyrrole derivatives having Janus kinase (JAK) and Src inhibitory activities, while WO2007 / 110344 claims protection for pyrimidinyl-pyrrole compounds having inhibitory activity against Cdc7 protein kinase activity.

[0006] Drug metabolism and pharmacokinetics (DMPK) are primarily related to safety assessments during drug discovery and development. In addition to sufficient potency towards the target protein, an acceptable safety profile is required to increase the chances of a candidate drug becoming a successful therapy.

[0007] In light of the above, there is a strong need to develop Cdc7 inhibitors for the treatment of cancer and other diseases. The inventors have now identified novel pyrrole carboxamide compounds with inhibitory activity against the Cdc7 protein kinase. The compounds of this invention are potent inhibitors of the Cdc7 kinase and, surprisingly, exhibit enhanced metabolic stability properties compared to compounds of the same chemical class disclosed in the prior art. These improved properties will be discussed in more detail in the "Experimental Section" below.

[0008] Due to the crucial role of PK, especially Cdc7, in regulating cell proliferation, these pyrrole carboxamide derivatives are particularly useful for the treatment of cancer as well as a variety of cell proliferation disorders and immune-related disorders. Invention Overview Therefore, the first object of the present invention is to provide a substituted pyrrole carboxamide compound represented by formula (I). in: R1 is a heteroaryl group selected from the group consisting of: , , , and in: Ra, Rb, and Rc are independently hydrogen, optionally substituted straight-chain or branched (C1-C6) alkyl, or optionally substituted straight-chain or branched (C2-C6) alkenyl. R2 is a substituted aryl or substituted heteroaryl ring having one to three substituents selected from the following: halogen, nitro, amino, (C1-C6)alkylamino, aminocarbonyl, optionally substituted straight-chain or branched (C1-C6)alkyl, optionally substituted straight-chain or branched (C1-C6)alkoxy, optionally substituted straight-chain or branched polyfluorinated (C1-C6)alkyl and optionally substituted straight-chain or branched polyfluorinated (C1-C6)alkoxy. The condition is that 2,5-disubstituted phenyl groups are excluded; R3 is hydrogen, optionally substituted straight-chain or branched (C1-C4) alkyl, optionally substituted (C3-C6) cyclic hydrocarbon group, or optionally substituted (C5-C6) heterocyclic group. R4 is hydrogen, optionally substituted straight-chain or branched (C1-C6) alkyl, or optionally substituted straight-chain or branched (C2-C6) alkenyl; and R5 is a straight-chain or branched (C1-C3) alkyl group containing hydrogen, halogen, or optionally substituted hydrogen. Or its pharmaceutically acceptable salt.

[0010] The preferred compound of formula (I) is the following compound, wherein: R1 is a heteroaryl group selected from group (A), group (B), group (C), group (D) and group (E) that is optionally substituted; in: Ra, Rb, and Rc are independently hydrogen or optionally substituted straight-chain or branched (C1-C6) alkyl groups; R2 is a 2,4-disubstituted phenyl, a 4,6-disubstituted pyridin-3-yl, a 2,6-disubstituted pyridin-3-yl, or a 3,5-disubstituted pyridin-2-yl; and R3, R4, and R5 are defined as above; A more preferred compound of formula (I) is the following compound, wherein: R2 is a 2,4-disubstituted phenyl group; R3 is hydrogen or a straight-chain or branched (C1-C4) alkyl chain that may be substituted; R5 is hydrogen; and R1 and R4 are defined as above.

[0011] Even more preferred compounds of formula (I) are those that are: R4 is hydrogen; and R1, R2, R3, and R5 are defined as above; Preferred specific compounds of formula (I) or pharmaceutically acceptable salts thereof are the compounds listed below: 2-(3-chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 1); 2-(4-chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 2); 2-(2-chloro-4-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 3); 2-(2,4-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 4); 2-[2-chloro-4-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 5); 2-(2,3-difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 6); 2-(2,3-dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 7); 2-[4-methyl-2-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 8); 2-(2-chloro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 9); 2-(2,3-difluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 10); 2-[2-methyl-4-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 11); 2-(2-fluoro-3-methoxyphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 12); 2-(2-chloro-3-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 13); 2-(2-fluoro-3-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 14); 2-[2-methyl-3-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 15); 2-[4-methoxy-2-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 16); 2-[2-chloro-4-(difluoromethoxy)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 17); 2-(3,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 18); 2-(3,4-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 19); 2-(3-ethoxy-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 20); 2-(4-methyl-3-nitrophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 21); 2-(3-carbamoyl-4-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 22); 2-(2-fluoro-4-methylphenyl)-N-[2-(pyrrolidine-1-yl)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 23); N-[2-(dimethylamino)ethyl]-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 24); 2-(2-fluoro-4-methylphenyl)-N-[2-(morpholin-4-yl)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 25); N-[(1S,2R)-2-aminocyclohexyl]-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 26); 2-(2-fluoro-4-methylphenyl)-N-(furan-2-ylmethyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 27); N-(fluoroethyl)-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 28); 2-(2-fluoro-4-methylphenyl)-N-[2-(methylamino)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 29); 2-(2-fluoro-4-methylphenyl)-N-(1-methylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 30); 2-(dibenzo[b,d]thiophen-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 31); 2-(4-methylnaphth-1-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 32); 2-(3-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 33); 5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-2-[4-(trifluoromethoxy)phenyl]-1H-pyrrolo-3-carboxamide (compound 34); 2-(1-benzothiophene-3-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 35); 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 36); 2-(4-fluoro-2-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 37); 2-(2-fluoro-4-methylphenyl)-4-iodo-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 38); 4-Bromo-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 39); 4-Ethyl-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (Compound 40); 2-(2-fluoro-4-methylphenyl)-4-(propyl-2-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 41); 5-(6-aminopyrimidin-4-yl)-2-(2,4-dichlorophenyl)-1H-pyrrole-3-carboxamide (Compound 42) 2-(2,4-Dichlorophenyl)-5-(1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide (compound 43); 2-(2,4-Dichlorophenyl)-5-(3-methyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide (compound 44); 5-(2-amino-1,3-thiazolyl-4-yl)-2-(2,4-dichlorophenyl)-1H-pyrrole-3-carboxamide (compound 45); 2-(2,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 46); 2-(2,4-Dichlorophenyl)-5-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 47); 2-(2,4-Dichlorophenyl)-5-[3-(trifluoromethyl)-1H-pyrazol-4-yl]-1H-pyrrole-3-carboxamide (compound 48); 2-(2-fluoro-4-methylphenyl)-5-(1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide (compound 49); 5-(3,5-dimethyl-1H-pyrazol-4-yl)-2-(2-fluoro-4-methylphenyl)-1H-pyrrole-3-carboxamide (compound 50); 2-(2-fluoro-4-methylphenyl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide (compound 51); 2-(2-fluoro-4-methylphenyl)-5-(3-methyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide (compound 52); 2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 53); 2-(2,4-Dichlorophenyl)-1-(2-hydroxyethyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 54); 2-(2,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-(3,3,3-trifluoropropyl)-1H-pyrrolo-3-carboxamide (Compound 55); 2-(2,4-dichlorophenyl)-1-methyl-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 56); and 2-(2,4-Dichlorophenyl)-1-ethyl-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 57).

[0012] If a stereogenic center or another form of asymmetric center is present in the compounds of the present invention, then all such forms of one or more optical isomers, including enantiomers and diastereomers, are intended to be included herein. Compounds containing a stereogenic center can be used as racemic mixtures, enantiomerically enriched mixtures, or racemic mixtures can be separated using well-known techniques, and individual enantiomers can be used. Such procedures include standard chromatographic techniques or crystallization, with standard chromatographic techniques including chromatography using a chiral stationary phase. General methods for separating compounds containing one or more asymmetric centers are reported, for example, in Jacques, Jean; Collet, André; Wilen, Samuel H., Enantiomers, Racemates, and Resolutions, John Wiley & Sons Inc., New York (NY), 1981.

[0013] In the case where the compound has an unsaturated carbon-carbon double bond, both the cis (Z) isomer and the trans (E) isomer are within the scope of this invention.

[0014] In cases where compounds may be present in tautomeric forms such as keto-enol tautomers, each tautomeric form is intended to be included in the invention, whether present in equilibrium or primarily in one form.

[0015] Pharmaceutically acceptable salts of compounds of formula (I) include salts with inorganic or organic acids such as nitric acid, hydrochloric acid, hydrobromic acid, sulfuric acid, perchloric acid, phosphoric acid, acetic acid, trifluoroacetic acid, propionic acid, glycolic acid, lactic acid, oxalic acid, fumaric acid, malonic acid, malic acid, maleic acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, hydroxyethanesulfonic acid, and salicylic acid.

[0016] Pharmaceutically acceptable salts of compounds of formula (I) also include salts with inorganic or organic bases, such as hydroxides, carbonates or bicarbonates, acyclic or cyclic amines of alkali or alkaline earth metals (especially sodium, potassium, calcium, ammonium or magnesium).

[0017] Another object of the present invention is a compound of formula (I), wherein one or more hydrogen atoms are replaced by one or more deuterium atoms.

[0018] The term "(C1-C6)alkyl" refers to an aliphatic (C1-C6) hydrocarbon chain that can be straight-chain or branched and contains only carbon-carbon single bonds. Representative examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, n-hexyl, and similar groups.

[0019] The term “(C3-C6)cycloalky”, unless otherwise provided, refers to a 3- to 6-membered all-carbon monocyclic ring that may contain one or more double bonds but does not have a fully conjugated π-electron system.

[0020] Examples of (C3-C6) cycloalkyl groups are, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, and cyclohexadienyl.

[0021] The term "(C5-C6) heterocyclic group" refers to a 5- or 6-membered saturated or partially unsaturated carbon ring in which one or more carbon atoms are replaced by heteroatoms such as nitrogen, oxygen, and sulfur. Non-limiting examples of heterocyclic groups include, for example, pyranyl, tetrahydropyranyl, pyrrolylyl, pyrrololinyl, imidazolinyl, imidazolinyl, pyrazolealkyl, pyrazolelinyl, thiazolinyl, thiazolinyl, dihydrofuranyl, tetrahydrofuranyl, tetrahydropyridyl, 1,3-dioxanepentyl, piperidinyl, piperazineyl, morpholinyl, and similar groups. The heterocyclic ring may optionally be further fused or linked to aromatic or non-aromatic carbon rings or heterocycles.

[0022] The term "(C2-C6)alkenyl" refers to an aliphatic straight-chain or branched (C2-C6) hydrocarbon chain containing at least one carbon-carbon double bond. Representative examples include, but are not limited to, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, or 2-butenyl groups and similar groups.

[0023] The term "aryl" refers to a monocyclic, dicyclic, or polycyclic hydrocarbon having a system of one to four rings, optionally further fused or linked to each other by single bonds, wherein at least one of the carbon rings is "aromatic," and the term "aromatic" refers to a fully conjugated π-electron bond system. Non-limiting examples of such aryl groups are phenyl groups, α-naphthyl groups or β-naphthyl groups, α-tetrahydronaphthyl groups or β-tetrahydronaphthyl groups, biphenyl groups, and indanyl groups.

[0024] The term "heteroaryl" refers to an aromatic heterocycle, typically a 5- to 6-membered heterocycle having 1 to 3 heteroatoms selected from N, O, or S; the heteroaryl ring may optionally be further fused or linked to aromatic and non-aromatic carbon rings and heterocycles. Non-limiting examples of such heteroaryl groups include, for example, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, imidazolyl, thiazolyl, isothiazolyl, pyrroleyl, furanyl, oxazolyl, isoxazolyl, pyrazolyl, thiophene, thiadiazolyl, oxadiazolyl, indazole, cenylyl, benzo[1,3]-dioxanepentenyl, benzo[1,4]dioxinyl, benzothiazolyl, benzyl... Thiophene, benzofuran, isoindolin, benzimidazol, benzoxazol, quinolin, isoquinolin, 1,2,3-triazol, 1-phenyl-1,2,3-triazol, 2,3-dihydroindolyl, 2,3-dihydrobenzofuran, 2,3-dihydrobenzothiophene, benzopyran, 2,3-dihydrobenzoxazin, 2,3-dihydroquinoxalin and similar groups.

[0025] When we use the term "halogen," we mean fluorine, chlorine, bromine, or iodine.

[0026] With regard to the terms “polyfluorinated (C1-C6)alkyl” or “polyfluorinated (C1-C6)alkoxy”, we mean any (C1-C6)alkyl group or (C1-C6)alkoxy group as defined above that is substituted with more than one fluorine atom, such as, for example, trifluoromethyl, trifluoroethyl, 1,1,1,3,3,3-hexafluoropropyl, trifluoromethoxy and similar groups.

[0027] For the term “hydroxy (C1-C6)alkyl”, we mean any (C1-C6)alkyl group as defined above that has a hydroxyl group, such as, for example, hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl and similar groups.

[0028] According to the present invention and unless otherwise provided, R1, R2, R3, R4, R5, Ra, Rb, and Rc may optionally be substituted in any free position therewith by one or more groups, for example, one to six groups, said one or more groups being independently selected from: hydroxyl, (C1-C6)alkoxyhydroxy(C1-C6)alkyl, halogen, nitro, oxo (=O), cyano, (C1-C6)alkyl, polyfluorinated (C1-C6)alkyl, polyfluorinated (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, aryl, aryl(C1-C6)alkyl, (C1-C6)alkylaryl, aryl(C1-C6)alkoxy, heteroaryl, heteroaryl (C1-C6)alkyl, (C1-C6)alkylheteroaryl, heterocyclic, heterocyclic (C1-C6)alkyl, (C1-C6)alkylheterocyclic, (C1-C6)alkylheterocyclic (C1-C6)alkyl, tri(C1-C6)alkylsilyl, (C3-C7)cycloalkyl, aryloxy, heterocyclic oxy, methylenedioxy, (C1-C6)alkylcarbonyloxy, arylcarbonyloxy, di(C1-C6)alkylaminoheterocyclic (C1-C6)alkyl, (C3-C7)cycloalkenyloxy, heterocyclic carbonyloxy, (C1-C6)alkylaminooxy, carboxyl, (C1-C6)alkoxycarbonyl, aryloxycarbonyl, (C3-C7)cycloalkyloxycarbonyl, nitrate alkyl, amino, heterocyclic (C1-C6)alkoxycarbonylamino, urea, (C1-C6)alkylamino, amino (C1-C6)alkyl, di(C1-C6)alkylamino, arylamino, diarylamino, heterocyclic amino, formylamino, (C1-C6)alkylcarbonylamino, arylcarbonylamino, heterocyclic carbonylamino, aminocarbonyl, (C1-C6)alkylaminocarbonyl, di(C1-C6)alkylaminocarbonyl, arylaminocarbonyl, heteroarylaminocarbonyl, arylaminocarbonyl (C1-C6)alkyl, (C3-C7)cycloalkylaminocarbonyl, heterocyclic aminocarbonyl, (C1-C6)alkoxycarbonylamino, hydroxyaminocarbonyl, (C1-C6)alkoxyimino, (C1-C6)alkylsulfonylamino, arylsulfonylamino, heterocyclic sulfonylamino, formyl, (C1-C6)alkylcarbonyl, arylcarbonyl, (C3-C7)cycloalkylcarbonyl, heterocyclic carbonyl, heterocyclic carbonyl (C1-C6)alkyl, (C1-C6)alkylsulfonyl, polyfluorinated (C1-C6)alkylsulfonyl, arylsulfonyl, aminosulfonyl, (C1-C6)alkylaminosulfonyl, di(C1-C6)alkylaminosulfonyl, arylaminosulfonyl, heterocyclic aminosulfonyl, arylthio, (C1-C6)alkylthio; whenever appropriate, each of the substituents above may be further substituted by one or more of the groups mentioned above.

[0029] From the entire above, it will be clear to those skilled in the art that any group whose name is a compound name, such as, for example, "arylamino", must be intended to be interpreted as conventionally derived from the part from which it is derived, for example, by an amino group substituted with an aryl group, wherein the aryl group is as defined above.

[0030] Similarly, any term such as (C1-C6)alkylthio, (C1-C6)alkylamino, di(C1-C6)alkylamino, (C1-C6)alkoxycarbonyl, (C1-C6)alkoxycarbonylamino, heterocyclic carbonyl, heterocyclic carbonylamino, (C3-C7)cycloalkyloxycarbonyl and similar groups, including those wherein the (C1-C6)alkyl moiety, (C1-C6)alkoxy moiety, aryl moiety, (C3-C7)cycloalkyl moiety and heterocyclic moiety are groups as defined above.

[0031] This invention also provides a process for preparing compounds of general formula (I) as defined above, the process being carried out using the reaction routes and synthetic schemes described below, employing techniques available in the art and readily available starting materials. The preparation of certain embodiments of the invention is described in the following examples, but those skilled in the art will recognize that the described preparations can be readily adapted to prepare other embodiments of the invention. For example, the synthesis of non-exemplary compounds according to the invention can be carried out with obvious modifications to those skilled in the art, such as by appropriately protecting interfering groups, by suitably replacing reagents with other reagents known in the art, or by conventional modifications to the reaction conditions. Alternatively, other reactions mentioned herein or known in the art will be considered suitable for the preparation of other compounds of the invention.

[0032] The compounds of the present invention can be prepared from readily available starting materials using the following general methods and procedures. Unless otherwise indicated, the starting materials are known compounds, or can be prepared from known compounds according to well-known procedures. It should be understood that, while describing typical or preferred process conditions (i.e., reaction temperature, time, molar ratio of reactants, solvent, pressure), different process conditions may also be used unless otherwise stated. Optimal reaction conditions may vary depending on the reactants or solvents used, but such conditions can be determined by those skilled in the art through conventional optimization procedures.

[0033] Compounds of general formula (I) as defined above can be prepared according to the general synthetic methods described below in schemes A, B and C.

[0034] Preparation of compound (I), wherein R1 is a heteroaryl group selected from formulas (A), (B), (C), (D), and (E); R2 is a substituted aryl or substituted heteroaryl ring having one to three substituents selected from: halogen, nitro, amino, (C1-C6)alkylamino, aminocarbonyl, optionally substituted straight-chain or branched (C1-C6)alkyl, optionally substituted straight-chain or branched (C1-C6)alkoxy, optionally substituted... A straight-chain or branched polyfluorinated (C1-C6) alkyl group and optionally substituted straight-chain or branched polyfluorinated (C1-C6) alkoxy group; R3 is H, optionally substituted straight-chain or branched (C1-C4) alkyl chain, optionally substituted (C3-C6) cyclic hydrocarbon group or optionally substituted (C5-C6) heterocyclic group; R4 is hydrogen and R5 is hydrogen, halogen or optionally substituted straight-chain or branched (C1-C3) alkyl group, which can be obtained according to Scheme A below: Option A Therefore, the process anticipates the following steps: Step 1) Metal-catalyzed coupling reaction of compound (II) with a suitable organoboronic acid derivative of formula (III): Wherein R5 is hydrogen or optionally substituted straight-chain or branched (C1-C3) alkyl group, and X is a halogen. Wherein R1 is a heteroaryl group of formula (A), formula (B), formula (C), formula (D) or formula (E); Step 2) Halogenation of the compound of formula (IV) thus obtained: Where R1 and R5 are defined as in step 1 above, thus obtaining compound (V): Where R1 and R5 are defined according to step 1 above, and X is a halogen; Step 3) Metal-catalyzed coupling reaction of compound (V) with a suitable organoboronic acid derivative of formula (VI): Wherein R2 is a substituted aryl or substituted heteroaryl ring having one to three substituents selected from the following: halogen, nitro, amino, (C1-C6)alkylamino, aminocarbonyl, optionally substituted straight-chain or branched (C1-C6)alkyl, optionally substituted straight-chain or branched (C1-C6)alkoxy, optionally substituted straight-chain or branched polyfluorinated (C1-C6)alkyl, and optionally substituted straight-chain or branched polyfluorinated (C1-C6)alkoxy, in order to obtain the compound of formula (VII): R1 and R5 are defined according to step 1 above, and R2 is defined according to step 3; Transformation 1) The compound of formula (VII) obtained from step 3, wherein R5 is hydrogen, can be transformed into a compound of formula (VII) wherein R5 is halogen (X) under the conditions already reported in step 2 above. Step 4) Protect the compound of formula (VII) obtained from step 3 or transformation 1 by reacting it with a suitable protecting group: Wherein R1 and R2 are defined according to steps 1 and 3 above, respectively, and R5 is hydrogen, halogen, or optionally substituted straight-chain or branched (C1-C3) alkyl, in order to obtain a carboxylic acid ester of formula (VIII): R1, R2, and R5 are defined as above, and PG is a protecting group, such as trimethylsilylethoxymethyl (SEM), tert-butyloxycarbonyl (BOC), or benzenesulfonyl. Step 5) The carboxylic acid ester of formula (VIII) is hydrolyzed under basic conditions to produce the carboxylic acid of formula (IX): R1, R2, R5, and PG are defined according to step 4 above; Step 6) Amidation of the intermediate of formula (IX) by reacting with an amine derivative of formula (X): R3 is hydrogen, optionally substituted straight-chain or branched (C1-C4) alkyl chain, optionally substituted (C3-C6) cyclic hydrocarbon group or optionally substituted (C5-C6) heterocyclic group. Step 7) Deprotection of the obtained compound of formula (XI): Wherein R1, R2, R5, and PG are as defined above in step 5, and R3 is as defined in step 6, to provide compound (I): R1, R2, R3, and R5 are as defined above, and R4 is hydrogen; or According to scheme A1 below, an intermediate compound of formula (VIII) where R5 is a halogen can be converted into an intermediate of formula (XI) where R5 is a straight-chain or branched C1-C3 alkyl chain: Option A1 Therefore, the process anticipates the following steps: Transformation 2) The compound of formula (VIII), wherein R1 and R2 are converted to the compound of formula (VIII) according to the conditions known in the art for palladium-catalyzed reactions as reported in step 3 of scheme A, wherein R5 is an optionally substituted straight-chain or branched (C1-C3) alkenyl chain: , Compound (VIII) is then reacted under the conditions reported in steps 5 and 6 of scheme A to obtain compound (XIa), wherein R1, R2 and R5 are as defined above; Transformation 3) The compound thus obtained, wherein R5 is a compound of formula (XIa) as defined above, is transformed into a compound of formula (XI) wherein R5 is an optionally substituted straight-chain or branched (C1-C3) alkyl group, according to conditions known in the art for double bond reduction / hydrogenation: .

[0035] Alternatively, a compound of formula (I), wherein R1 is an optionally substituted heteroaryl group of formula (A), (B), (C), (D), or (E); R2 is a substituted aryl or substituted heteroaryl ring having one to three substituents; R3 and R4 are hydrogen, and R5 is hydrogen or an optionally substituted straight-chain or branched (C1-C3) alkyl group, can be prepared according to scheme B below: Option B Therefore, the process anticipates the following steps: Step 8) Protected (XII) compound: Wherein R2 is a substituted aryl or substituted heteroaryl ring having one to three substituents, and R5 is hydrogen or optionally substituted straight-chain or branched (C1-C3) alkyl. Step 9) Halogenation of the compound of formula (XIII) thus obtained: R2 and R5 are defined as described above in step 8, and PG is a protecting group, such as SEM, BOC, or benzenesulfonyl. Step 10) Metal-catalyzed coupling reaction of the obtained compound of formula (XIV) with a suitable organoboronic acid derivative of formula (III): R2, R5, and PG are defined according to step 9 above, and X is a halogen. Wherein R1 is a heteroaryl group of formula (A), formula (B), formula (C), formula (D) or formula (E); Step 11) Hydrolysis of the compound of formula (XV) thus obtained: R1, R2, R5 and PG are defined in step 10 above, thereby producing the amide intermediate of the corresponding formula (XVI); Step 12) Deprotection of compound (XVI) to provide compound (I): R1, R2, and R5 are defined as above, and R3 and R4 are hydrogen.

[0036] Alternatively, compounds of formula (I) can be prepared according to scheme C below, wherein R1 is a heteroaryl group of formula (A), (B), (C), (D), or (E); R2 is a substituted aryl or substituted heteroaryl ring having one to three substituents; R3 is hydrogen; R4 is hydrogen, optionally substituted straight-chain or branched (C1-C6) alkyl, or optionally substituted straight-chain or branched (C2-C6) alkenyl; and R5 is hydrogen or optionally substituted straight-chain or branched (C1-C4) alkyl chain. Option C Therefore, the process anticipates the following steps: Step 13) React the derivative of formula (XII) with the halo derivative of formula (XVII) in the presence of a base or by adding a metal catalyst: Wherein R2 is a substituted aryl or substituted heteroaryl ring having one to three substituents, and R5 is hydrogen or optionally a substituted straight-chain or branched (C1-C3) alkyl group. Wherein R4 is an optionally substituted straight-chain or branched C1-C6 alkyl, or an optionally substituted straight-chain or branched C2-C6 alkenyl, and X is a halogen. Step 14) Halogenation of the compound of formula (XVIII) thus obtained: R2, R4, and R5 are defined according to step 13 above; Step 15) Metal-catalyzed coupling reaction of the obtained compound of formula (XIX) with a suitable organoboronic acid derivative of formula (III): Where X is a halogen and R2, R5, and R4 are as defined above. Where R1 is a heteroaryl group (A), (B), (C), (D), or (E); Step 16) Hydrolysis of the intermediate of formula (XX) thus obtained: To provide compounds of formula (I): R1, R2, R4, and R5 are defined as above, and R3 is hydrogen.

[0037] According to step 1 of scheme A, the metal-catalyzed coupling reaction of compound (II) with organoboron derivative of general formula (III) to provide compound (IV) can be carried out in a variety of ways. Preferably, compound (IV) can be prepared from intermediate of formula (II) by Pd-catalyzed Suzuki-Miyaura coupling. Transition metal-catalyzed coupling of (hetero)aryl halides with (hetero)arylboronic acids or boronic esters is well known to those skilled in the art, see reference: a) Miyaura, Norio; Suzuki, Akira (1979). “Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds”. Chemical Reviews 95(7): 2457-2483; b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions, Diederich, F. and Stang, PJ (eds.); Wiley-VCH: New York, 1998, pp. 49-97. In the so-called Suzuki-Miyaura reaction, the coupling reaction of (hetero)arylboronic acid or boronic ester with (hetero)aryl halide is usually initiated by palladium complexes. Phosphine-palladium complexes such as [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride are used for this reaction, but bis(triphenylphosphine)palladium(II) chloride and tetra(triphenylphosphine)palladium(O) can also be used. Adding bases such as potassium phosphate, sodium carbonate, cesium carbonate, potassium carbonate, potassium tert-butoxide, tetraethylammonium hydroxide, triethylamine, and tetrahydrofuran, dioxane, N , N Dimethylformamide, ethanol, toluene, water, or mixtures thereof can be used as reaction media. Typically, the temperature range is from room temperature to 150°C. Conventional heating combined with microwave irradiation can be employed. Reaction durations range from approximately 30 minutes to approximately 96 hours. Various Pd-catalyst / base / solvent combinations have been described in the literature, allowing for fine-tuning of reaction conditions to enable a wide range of additional functional groups on the two coupling partners.

[0038] According to step 2 of scheme A, compound (V) can be obtained by halogenating compound (IV) in a variety of ways and experimental conditions known in the art. Preferably, the reaction is carried out in the presence of N-bromosuccinimide, N-iodosuccinimide, N-chlorosuccinimide, bromine, iodine, hydrobromic acid / hydrogen peroxide, in a suitable solvent such as acetonitrile, methanol, tetrahydrofuran, N,N-dimethylformamide, dioxane, dimethyl sulfoxide, acetic acid, water, or mixtures thereof, at a temperature ranging from about 0°C to reflux and for a duration varying from about 1 hour to about 96 hours.

[0039] According to step 3 of scheme A, the metal-catalyzed coupling reaction of the compound of formula (V) with the organoboronic acid derivative of general formula (VI) to provide the compound of formula (VII) can be carried out in a variety of ways as described in step 1 of scheme A.

[0040] According to step 4 of scheme A, compound (VII) can be converted into compound (VIII) using various methods and experimental conditions well known in the art for protecting secondary amine groups. Preferably, the reaction is carried out by treatment with an excess of (trimethylsilyl)ethoxymethyl chloride in a suitable solvent such as tetrahydrofuran or dichloromethane in the presence of a base such as, for example, sodium hydride. Typically, the reaction is carried out at temperatures ranging from 0°C to reflux and for durations varying from about 30 minutes to about 96 hours. The benzenesulfonyl group can be converted by treatment with an excess of (trimethylsilyl)ethoxymethyl chloride in a suitable solvent such as, for example, triethylamine. N , N -Diisopropylethylamine is introduced by reacting benzenesulfonyl chloride in solvents such as dichloromethane and acetonitrile in the presence of a proton scavenger, at temperatures ranging from room temperature to reflux. The tert-butyloxycarbonyl (Boc) group can be introduced by reacting with benzenesulfonyl chloride in solvents such as sodium bicarbonate, triethylamine, etc. N , N -Diisopropylethylamine is introduced by treatment with an excess of ditert-butyl dicarbonate in the presence of a base, in solvents such as tetrahydrofuran, dioxane, or dichloromethane, at temperatures ranging from room temperature to reflux.

[0041] According to step 5 of scheme A, the hydrolysis of the carboxylic acid ester of formula (VIII) to the carboxylic acid of formula (IX) can be carried out in a variety of ways. Preferably, the reaction is carried out in the presence of a suitable base such as, for example, sodium hydroxide, potassium hydroxide, or lithium hydroxide and H₂O, in a suitable solvent such as, for example, methanol, ethanol, 1,4-dioxane, or tetrahydrofuran. Typically, the reaction is carried out at a temperature ranging from room temperature to 150°C, and for a duration varying from about 1 hour to about 96 hours. Conventional heating combined with microwave irradiation can be used.

[0042] According to step 6 of scheme A, the conversion of the carboxylic acid of formula (IX) to the formamide of formula (XI) can be accomplished using various methods and experimental conditions well-known in the art for the preparation of formamides. As an example, the compound of formula (IX) can be... O -(benzotriazol-1-yl)- N,N,N',N' -Tetramethylureon tetrafluoroborate, hydroxybenzotriazole, dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-ethyl-3-(3'-dimethylamino)carbodiimide hydrochloride react with the ammonium salt of 1-hydroxybenzotriazole or with the amine NH₂R₃(X). Preferably, the reaction is carried out in a suitable solvent such as, for example, tetrahydrofuran, dichloromethane, toluene, dioxane, etc. N , N -Dimethylformamide, N , N -Dimethylacetamide, and in substances such as, for example, triethylamine, N , N - In the presence of a proton scavenger, diisopropylethylamine is reacted at temperatures ranging from 0°C to reflux for a duration ranging from about 30 minutes to about 96 hours. Alternatively, the compound of formula (IX) can be converted to its corresponding acyl chloride in the presence of thionyl chloride or oxalyl chloride in a suitable solvent such as toluene, dichloromethane, chloroform, diethyl ether, tetrahydrofuran, or dioxane, at temperatures ranging from about -10°C to reflux for a duration ranging from about 1 hour to about 96 hours. The acyl chloride can be separated by evaporating the solvent and further reacted in a suitable solvent such as toluene, dichloromethane, chloroform, diethyl ether, tetrahydrofuran, or dioxane with a 33% ammonium hydroxide solution or with amine NH₂R₃(X) at temperatures ranging from about -10°C to reflux for a duration ranging from about 1 hour to about 96 hours.

[0043] According to step 7 of scheme A, the removal of the protecting group PG on the pyrrole ring of compound (XI) can be carried out according to procedures well known in the art. Depending on the selected protecting group, the following conditions can be used: 2-(trimethylsilyl)ethoxymethyl (SEM) can be removed at room temperature or below in solvents such as tetrahydrofuran, dichloromethane, with tetrabutylammonium fluoride, pyridine hydrogen fluoride, or trifluoroacetic acid; benzenesulfonyl (Bs) group can be removed in solvents such as methanol, tetrahydrofuran, dioxane, with potassium hydroxide, sodium hydroxide, potassium carbonate, or lithium hydroxide in the range from room temperature to reflux temperature; tert-butyloxycarbonyl (Boc) can be removed at temperatures ranging from room temperature to 130°C in the presence of trifluoroacetic acid in dichloromethane or by means of dimethoxyethane, N , N Sodium carbonate is removed from dimethylformamide.

[0044] According to step 8 of scheme B, the conversion of the compound of general formula (XII) to the compound of formula (XIII) can be accomplished by the reaction already described in step 4 of scheme A.

[0045] According to step 9 of scheme B, the halogenation of the compound of formula (XIII) used to obtain the compound of formula (XIV) can be carried out as described in step 2 of scheme A above.

[0046] According to step 10 of scheme B, the metal-catalyzed coupling reaction of the compound of formula (XIV) with the organoboronic acid derivative of general formula (III) to provide the compound of formula (XV) can be carried out in a variety of ways as described in step 1 of scheme A.

[0047] According to step 11 of scheme B, the hydrolysis of compound (XV) to compound (XVI) can be carried out in a variety of ways according to conventional methods for converting cyano groups to amides. Preferably, the reaction is carried out in the presence of a suitable acid or base (such as, for example, sulfuric acid, hydrochloric acid, methanesulfonic acid, indium chloride, sodium hydroxide or potassium hydroxide, sodium carbonate or potassium carbonate) or a suitable reagent (such as hydrogen peroxide, sodium perborate or acetaldehyde oxime) in a suitable solvent such as, for example, methanol, ethanol, n-butanol, 1,4-dioxane, toluene, water or mixtures thereof. Typically, the reaction is carried out at temperatures ranging from room temperature to reflux and for a duration ranging from about 1 hour to about 96 hours.

[0048] According to step 12 of scheme B, the removal of the protecting group PG on the pyrrole ring of the compound of formula (XVI) used to obtain compound of formula (I) can be carried out as described above in step 7 of scheme A.

[0049] According to step 13 of scheme C, the reaction of compound (XII) providing compound (XVIII) with a halogenated derivative of general formula (XVII) can be carried out in the presence of a base such as sodium hydride, and tetrahydrofuran or dioxane can be used as the reaction medium. Typically, the temperature range is from 5°C to reflux. The reaction duration ranges from about 30 minutes to about 24 hours. Alternatively, the metal-catalyzed coupling reaction of compound (XIV) providing compound (Ic) with a halogenated derivative of general formula (V) can be carried out in the presence of tris(dibenzylacetone)palladium and tri-tert-butylphosphine. A base such as sodium carbonate, cesium carbonate, or potassium carbonate is added, and tetrahydrofuran, dioxane, N , N Dimethylformamide and toluene can be used as reaction media. Typically, the temperature range is from room temperature to 150°C. Conventional heating combined with microwave irradiation can be employed. The reaction duration ranges from approximately 30 minutes to approximately 24 hours.

[0050] According to step 14 of scheme C, the halogenation of the compound of formula (XVIII) for obtaining the compound of formula (XIX) can be carried out as described above in step 2 of scheme A.

[0051] According to step 15 of scheme C, the metal-catalyzed coupling reaction of the compound of formula (XIX) with the organoboronic acid derivative of general formula (III) to provide the compound of formula (XX) can be carried out in a variety of ways as described in step 1 of scheme A.

[0052] According to step 16 of scheme C, the hydrolysis of compound (XX) into compound (I) can be carried out as described in step 11 of scheme B above.

[0053] According to the transformation described in transformation 1), the conversion of compound (VII) to compound (VII) can be carried out in different ways and under different experimental conditions. Preferably, it is carried out in a manner similar to that reported with respect to step 2 of scheme A.

[0054] According to the transformation described in transformation 2), the derivation of compound (VIII) into compound (VIII) can be accomplished in a variety of ways as described in step 3 of scheme A.

[0055] According to the transformation described in transformation 3), the conversion of compound (XIa) to compound (XI) can be achieved using various methods and experimental conditions well known in the art for the reduction of double bonds. Preferably, the reaction is carried out in a suitable solvent such as methanol, ethanol, toluene, or tetrahydrofuran in the presence of a suitable catalyst such as, for example, palladium on carbon (10%), palladium acetate, or rhodium catalyst. Typically, the reaction is carried out at temperatures ranging from room temperature to 150°C and for durations varying from about 1 hour to about 96 hours.

[0056] From the entire foregoing, it will be clear to those skilled in the art that any compound of formula (I) having a functional group that can be further derived into another functional group is intended to be included within the scope of the present invention, derived by operating in accordance with methods well known in the art to obtain other compounds of formula (I).

[0057] When preparing compounds of general formula (I) according to any of the above variations of the process, optional functional groups in the starting materials, reagents, or intermediates that may produce undesirable side reactions need to be properly protected according to conventional techniques (see, for example, Green, Theodora W. and Wuts, Peter GM – Protective Groups in Organic Synthesis, 3rd ed., John Wiley & Sons Inc., New York (NY), 1999). Similarly, the conversion of these latter into free, deprotected compounds can be carried out according to known procedures.

[0058] Each compound of a general formula can be further transformed into other compounds of the same general formula using methods well known in the literature, as reported in the experimental section.

[0059] Depending on any variation of the process used to prepare the compound of formula (I), the starting materials and any other reactants are known or readily prepared by known methods.

[0060] Compounds of formula (XII) can be prepared according to the method described in WO2009133170A1.

[0061] Compounds of formula (II), (III), (VI), (X), and (XVII) are commercially available.

[0062] The final compound can be separated and purified using conventional procedures, such as chromatography and / or crystallization and salt formation.

[0063] Compounds of general formula (I) as defined above can be converted into pharmaceutically acceptable salts. Compounds of general formula (I) as defined above, or pharmaceutically acceptable salts thereof, can then be formulated with a pharmaceutically acceptable carrier or diluent to provide a pharmaceutical composition.

[0064] According to the synthetic process described above, the synthesis of compounds of general formula (I) can be carried out in a stepwise manner, thereby separating and purifying each intermediate by standard purification techniques such as column chromatography, if necessary, before proceeding with subsequent reactions. Alternatively, two or more steps of the synthetic sequence can be carried out in a so-called "one-pot" procedure as known in the art, thereby separating and purifying only the compounds obtained from the two or more steps.

[0065] The present invention also provides a method for treating diseases caused by and / or related to dysregulated Cdc7 kinase activity, the method comprising administering to a mammal, preferably a human, an effective amount of a compound according to formula (I) as defined above.

[0066] Furthermore, the present invention provides a compound of formula (I) as defined above, or a pharmaceutically acceptable salt thereof, for use in a method of treating diseases caused by and / or associated with dysregulated Cdc7 kinase activity, the method comprising administering an effective amount of the compound of formula (I) as defined above to a mammal, preferably a human, in the appropriate need.

[0067] Alternatively, the present invention provides the use of a compound of formula (I) as defined above, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for treating diseases caused by and / or associated with dysregulated Cdc7 kinase activity.

[0068] Preferably, the disease is selected from the group consisting of: cancer, cell proliferation disorders, and immune-related disorders. More preferably, the disease is cancer.

[0069] According to the most preferred embodiment of the invention, the cancer is selected from the group consisting of: carcinoma, such as bladder cancer, breast cancer, kidney cancer, liver cancer, colon cancer, lung cancer including small cell lung cancer, esophageal cancer, gallbladder cancer, ovarian cancer, pancreatic cancer, gastric cancer, cervical cancer, prostate cancer, head and neck cancer including squamous cell carcinoma, and skin cancer; lymphoid hematopoietic tumors, including leukemia, acute lymphoblastic leukemia, acute lymphoblastic leukemia, B-cell lymphoma, angioimmunoblastic T-cell lymphoma, Hodgkin lymphoma, non-Hodgkin lymphoma, pilocellular lymphoma, mantle cell lymphoma, and Burkitt's lymphoma. Lymphoma; hematopoietic tumors of the bone marrow system, including acute and chronic myeloid leukemia, myelodysplastic syndromes, and promyelocytic leukemia; tumors of mesenchymal origin, including fibrosarcoma and rhabdomyosarcoma; tumors of the central and peripheral nervous systems, including glioma, glioblastoma, glioblastoma multiforme, astrocytoma, oligodendroglioma, paraganglioma, neuroblastoma, and schwannoma; and other tumors, including melanoma, seminoma, teratoma, osteosarcoma, xeroderma pigmentosum, keratoacanthoma, thyroid cancer such as papillary thyroid carcinoma and medullary thyroid carcinoma, Kaposi's sarcoma, chondrosarcoma, cholangiocarcinoma, and head and neck tumors.

[0070] Other preferred diseases caused by and / or associated with dysregulated Cdc7 kinase activity are proliferative disorders, such as, for example, benign prostatic hyperplasia, familial adenomatous polyposis, polyposis, neurofibromatosis, psoriasis, vascular smooth muscle cell proliferation associated with atherosclerosis, pulmonary fibrosis, arthritis, glomerulonephritis, and postoperative stenosis and restenosis.

[0071] Another preferred disease caused by and / or associated with dysregulated Cdc7 kinase activity is immune-related disorders, including but not limited to: transplant rejection, skin disorders such as psoriasis, allergies, asthma, and autoimmune-mediated diseases such as rheumatoid arthritis (RA), systemic lupus erythematosus (SLE), Crohn's disease, and amyotrophic lateral sclerosis (ALS).

[0072] Furthermore, the present invention provides compounds of formula (I) as defined above, or pharmaceutically acceptable salts thereof, for use in methods of treating mammals in need of treatment in combination with radiotherapy or with chemotherapy regimens, targeted therapy regimens or immunotherapy regimens.

[0073] In one implementation, the chemotherapy regimen and / or targeted therapy regimen includes at least one cell inhibitor or cytotoxic agent.

[0074] Cell inhibitors or cytotoxic agents include, but are not limited to, antibiotics, alkylating agents, antimetabolites, hormones, immunotherapeutics, interferons, cyclooxygenase inhibitors (e.g., COX-2 inhibitors), matrix metalloproteinase inhibitors, telomerase inhibitors, tyrosine kinase inhibitors, anti-growth factor receptor agents, anti-HER2 agents, anti-EGFR agents, anti-angiogenic agents (e.g., angiogenesis inhibitors), farnesyl transferase inhibitors, ras-raf signaling pathway inhibitors, cell cycle inhibitors, CDKS inhibitors, tubulin binding agents, topoisomerase I inhibitors, topoisomerase II inhibitors, aromatase inhibitors, kinin inhibitors, therapeutic monoclonal antibodies, mTOR inhibitors, histone deacetylase inhibitors, platinum, and inhibitors of hypoxia response. Immunotherapy agents include PD-1 antagonists and antibodies that specifically bind to PD-1 or PD-L1.

[0075] If formulated as a fixed dose, such a combination product uses compounds of the present invention within the dose range described below and other pharmaceutically active agents within the approved dose range.

[0076] When combination formulations are not suitable, compounds of formula (I) can be used sequentially with known anticancer agents.

[0077] The compound of formula (I) of the present invention, suitable for administration to mammals such as humans, can be administered via conventional routes, and the dosage level depends on the patient's age, weight and condition, as well as the route of administration.

[0078] For example, suitable dosages for orally administered compounds of formula (I) can range from about 10 mg to about 1000 mg per dose, from once to five times daily. The compounds of the present invention can be administered in a variety of dosage forms, such as orally in the form of tablets, capsules, sugar or film-coated tablets, liquid solutions or suspensions; rectally in the form of suppositories; parenterally, such as intramuscularly, or by intravenous and / or intrathecal and / or intraspinal injection or infusion.

[0079] Pharmaceutical compositions containing the compounds of the present invention are typically prepared by conventional methods and administered in a suitable pharmaceutical form.

[0080] For example, solid oral formulations may contain diluents along with the active compound, such as lactose, dextrose, saccharose, sucrose, cellulose, corn starch, or potato starch; lubricants, such as silica, talc, stearic acid, magnesium stearate, or calcium stearate, and / or polyethylene glycol; binders, such as starch, gum arabic, gelatin, methylcellulose, carboxymethylcellulose, or polyvinylpyrrolidone; disintegrants, such as starch, alginate, alginate, or sodium starch glycolate; effervescent mixtures; dyes; sweeteners; humectants, such as lecithin, polysorbate, lauryl sulfate / salt; and non-toxic and pharmacologically inactive substances commonly used in pharmaceutical preparations. These pharmaceutical articles can be manufactured in known ways, such as by means of mixing processes, granulation processes, tableting processes, sugar coating processes, or film coating processes.

[0081] Liquid dispersions for oral administration can be, for example, syrups, emulsions, and suspensions.

[0082] As an example, the syrup may contain sucrose as a carrier or sucrose together with glycerol and / or mannitol and sorbitol.

[0083] Examples of carriers include suspensions and emulsions, which may contain natural gums, agar, sodium alginate, pectin, methylcellulose, carboxymethylcellulose, or polyvinyl alcohol.

[0084] Suspensions or solutions intended for intramuscular injection may contain a pharmaceutically acceptable carrier, such as sterile water, olive oil, ethyl oleate, glycols such as propylene glycol, and, if necessary, an appropriate amount of lidocaine hydrochloride.

[0085] Solutions intended for intravenous injection or infusion may contain sterile water as a carrier, or preferably they may be in the form of sterile solutions, aqueous solutions, isotonic solutions, saline solutions, or they may contain propylene glycol as a carrier.

[0086] Suppositories may contain a pharmaceutically acceptable carrier along with the active compound, such as cocoa butter, polyethylene glycol, polyoxyethylene sorbitan fatty acid ester surfactant, or lecithin.

[0087] The present invention also provides a pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (I) as defined above or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable excipient, carrier or diluent.

[0088] The present invention also provides pharmaceutical compositions comprising one or more chemotherapeutic agents having a compound of formula (I).

[0089] Furthermore, the present invention provides an in vitro method for inhibiting the activity of Cdc7 protein, the method comprising contacting the protein with an effective amount of a compound of formula (I) as defined above.

[0090] In addition, the present invention provides a product comprising a compound of formula (I) as defined above or a pharmaceutically acceptable salt thereof, and one or more chemotherapeutic agents, for use as a combination article in anticancer therapy, simultaneously, separately or sequentially.

[0091] Ultimately, the present invention provides compounds of formula (I) as defined above, or pharmaceutically acceptable salts thereof, for use as medicines.

[0092] Experimental Section The abbreviations and abbreviations used in this article have the following meanings: Biochemical assay The inhibitory activity of the proposed Cdc7 inhibitors and the potency of the selected compounds were determined by the methods reported below.

[0093] ADPGlo assay format The biochemical activity of the compound was determined by incubation with a specific enzyme and substrate, followed by quantification of the ADP product. The compound was serially diluted 4-fold from 10 μM to 0.0006 μM; in the case of a pre-incubation step, the enzyme was added to the inhibitor solution, and the mixture was incubated at room temperature (rt) for 30 minutes. When the enzyme was already present in the pre-incubation step, the reaction was initiated by adding the substrate and ATP; otherwise, the reaction was initiated by adding the substrate, ATP, and enzyme. The concentrations of ATP, substrate, and reaction buffer were described above. The assay was run in an automated manner on 384-well plates. Each 384-well plate contained several reference wells (total enzyme activity relative to enzyme completely inhibited by a specific inhibitor), which were used for Z' and signal-to-background ratio assessment. At the end of the incubation time, an equal volume of ADPGlo reagent 1 (Promega) was added to stop the reaction and remove all unreacted ATP. After 60 minutes, an equal volume of ADPGlo reagent 2 (Promega) was added to convert ADP to ATP, which was then converted to light via a luciferase reaction. The luminescence signal was read using a plate reader after 15 minutes.

[0094] Data obtained from two assay methods were analyzed using a custom version of the SW package "Assay Explorer". This custom version of "Assay Explorer" provides an S-shaped fit of eight-dilution curves using a 4-parameter logistic equation for IC analysis. 50 Determination: Where x is the logarithm of the inhibitor concentration and y is the response value; y starts from the bottom and reaches the top in an S-shape.

[0095] All information regarding plate dilution, distribution, assay type, target, and raw inhibition data is tracked via barcode reading and stored in an Oracle DB.

[0096] The biochemical activities of the compounds of the present invention obtained using the methods reported above are summarized in Table 1 below.

[0097] Table 1 * Compounds used in chlorate testing ** Compounds used as TFA salt test ND: Undetermined As summarized in Table 1, the compounds of the present invention exhibit significant activity against cell division cycle 7-related protein kinase (Cdc7).

[0098] Metabolic stability assay The intrinsic clearance value of the test item was determined by comparing the intrinsic clearance value in the presence and absence of the aldehyde oxidase inhibitor hydralazine hydrochloride. The aim of this study was to evaluate intrinsic clearance in vitro, metabolic stability of aldehyde oxidase (AO) activity, and metabolism of the test item in human hepatic cytosol. Intrinsic clearance was determined using a half-life method, measuring the disappearance of the substrate after 60 minutes of incubation with human hepatic cytosol. (The text abruptly ends here, so the translation stops as well.) Incubation was performed at a concentration of M. 1 The initial concentration of M was assumed to be << Km. HPLC-MS / MS was used to detect residual compounds during incubation. To determine the intrinsic clearance, samples were analyzed by high-performance liquid chromatography (HPLC) with an online mass spectrometer (MS) device. To determine the aldehyde oxidase activity of the cytosol (i.e., a positive control), phthalazine was incubated with human liver cytosol in the presence and absence of aldehyde oxidase inhibitors. On the day of incubation, the compound was dissolved in DMSO at a concentration of 10 mM. Aliquots of this solution were added to the test system to a final concentration of 1. M. The final incubator contained 0.1% DMSO.

[0099] At 37°C, aliquots of the test sample were added to human hepatic cytosol (1 mg / mL protein content) in Dulbecco buffer at pH 7.4 to achieve 1 The final concentration of M was determined. The culture was incubated in 48-well plates with shaking. The concentrations of 50 μL of the incubator were measured at 0, 5, 10, 20, 30, and 60 minutes of incubation. L equal portions of the sample were taken and poured into 80 ml of water. L of cold acetonitrile and 20 L in acetonitrile 1 In M warfarin (injection control), centrifuged at 2500 rpm for 20 minutes. The supernatant was immediately analyzed by LC-MS / MS.

[0100] In 10 In the presence of hydralazine hydrochloride (an aldehyde oxidase inhibitor), at 37°C, a concentration of 1 in Dulbecco buffer at pH 7.4 will be achieved. The test item M was incubated in duplicate in parallel for 60 minutes.

[0101] The concentration was increased to 1 in Dulbecco buffer at pH 7.4 by 37°C. The test item M was incubated alone for 60 minutes to check the chemical stability of the test item in parallel (negative control).

[0102] The intrinsic clearance rate (CLint) was calculated using the half-life method. Half-life and CLint were determined using LC-MS / MS based on the remaining concentration (area count) at different sampling points. The slope was calculated via linear regression analysis by plotting the natural logarithmic area of ​​the remaining compound against time, and then converted to half-life (t1 / 2) according to the following formula. CLint, expressed as L / min / mg protein: The formation of the phthalazine metabolite 2,3-diazanaphthone was determined using HPLC-MS / MS based on the concentration at different sampling points. The slope was calculated by plotting the metabolite concentration against time, and the maximum value was converted to the metabolite formation rate in pmol / min / mg.

[0103] Table 2 below reports the metabolic stability results of the compounds of the present invention compared with reference compound A (Ref. compd. A) and reference compound B (Ref. compd. B), which have been identified as the closest prior art. Reference compound A and reference compound B correspond to compounds (53) and (55) of PCT international application WO2007 / 110344, respectively.

[0104] Table 2 HLC: Human liver cytosol IntCl: Intrinsic clearance rate * Compounds used in chlorate testing ** Compounds used as TFA salt test As shown in Table 2, reference compound A or reference compound B exhibited poor metabolic stability when incubated in human hepatic cytosol, showing low half-lives (T1 / 1 = 14.8 min and 154 min, respectively) and low percentages of remaining compound after 60 min of incubation (40% and 70%, respectively). Surprisingly, under the same experimental conditions, the compounds of the present invention showed significantly better metabolic stability than those of the prior art.

[0105] In particular, the new compounds exhibited an increased half-life (225 minutes), a higher percentage of remaining compounds (85% in the worst case), and a reduced intrinsic clearance value, resulting in superior DMPK properties compared to reference prior art compounds, thus increasing their chances of becoming drug candidates.

[0106] Preparation of compound (I) For any specific compound of formula (I) of the invention, optionally in the form of a pharmaceutically acceptable salt, see the experimental section and claims. The compounds of the invention were synthesized using the methods described herein or other methods well known in the art, with reference to the following examples.

[0107] For the purpose of better illustrating the present invention, without causing any limitation to the present invention, the following embodiments are given.

[0108] As used herein, the symbols and conventions used in processes, schemes, and embodiments are consistent with contemporary scientific literature, for example... Journal of the American Chemical Society or Journal of Biological Chemistry The symbols and conventions used are consistent.

[0109] The compound name is an IUPAC name generated using the ACD Name (via Advanced Chemistry Development, Inc.).

[0110] Unless otherwise specified, all materials, including anhydrous solvents such as DMF, THF, and DCM, are obtained from commercial suppliers of the highest quality and used without further purification. All reactions involving air-sensitive or moisture-sensitive compounds are carried out under a nitrogen or argon atmosphere.

[0111] General purification and analytical methods Rapid chromatography was performed on silica gel (Merck grade 9395, 60A).

[0112] HPLC equipment by Waters Alliance TMThe HT 2795 system comprises a Waters 996PDA detector and a Waters mod. ZQ 2000 single quadrupole mass spectrometer equipped with an electrospray ionization (ESI) source. Instrument control, data acquisition, and data processing are provided via Empower 2 software and MassLynx 4.1 software.

[0113] HPLC was performed using YMC-Triart C18 (4.6 × 50 mm, 3) The column was run at 25 °C at a flow rate of 1.2 mL / min. Mobile phase B was 5 mM ammonium acetate buffer (95:5) with acetonitrile at pH 5.2, and mobile phase C was H₂O / acetonitrile (5:95); the gradient was from 10% C to 90% C over 5 min, then ramped up to 100% C over 0.1 min. The injection volume was 10 μL. The mass spectrometer was operated in both positive and negative ion modes, with the capillary voltage set to 3.5 kV (ES). + ) and 2.8kV (ES - The cone voltage is 14 V (ES). + ) and 28 V (ES) - The source temperature is 120°C; a full scan with a quality range from 100 amu to 800 amu is set.

[0114] The preparative HPLC setup consisted of a Shimadzu HPLC system equipped with an SCL-8A system controller, two LC-8A pumps, an SPD-6A UV spectrophotometer, and a manual Rheodyne injection system. Data acquisition (analog signal) and data processing were performed using Empower 2 software. Purification was performed using a Waters X-Terra MS RP18 (150 × 30 mm, 10 µm) column at 25 °C and a flow rate of 15 mL / min. Mobile phase A was 0.1% TFA in water / acetonitrile (95:5), or alternatively, mobile phase A was 0.05% NH3 in water / acetonitrile (95:5), and mobile phase B was H2O / acetonitrile (5:95); the gradient was from 10% B to 90% B over 15 min, then ramped up to 100% B over 0.1 min. The maximum injection volume was 500 μL.

[0115] 1 H-NMR spectra were recorded at an isothermal temperature of 28 °C on a 400.5 MHz aperture equipped with a 5 mm aperture. 1 H{ 15 N- 31The P} z-axis PFG indirect detection probe was used on a Varian INOVA 400 spectrometer, and the data were recorded on a spectrometer operating at 499.7 MHz and equipped with a 5 mm [missing information - likely a spectrometer or instrument]. 1 H{ 13 C- 15 On a Varian INOVA 500 spectrometer, the N} triple resonance indirect detection probe was used. The chemical shift of the residual solvent signal (DMSO-) was observed. d 6 : 1 H (2.50 ppm) was used as a reference. Data were reported as follows: chemical shift (δ), multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, br.s = broad singlet, dd = doublet, ddd = doublet of doublet, m = multiply), coupling constant (J, Hz), and proton number.

[0116] As previously reported (M. Colombo, FR Sirtori, V. Rizzo, Rapid Commun MassSpectrom 2004, 18(4), 511-517), ESI(+) high-resolution mass spectrometry (HRMS) was obtained on a Q-Tof Ultima (Waters, Manchester, UK) mass spectrometer directly connected to an Agilent 1100 micro-HPLC system (Palo Alto, US).

[0117] Example A Step 1 5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrolo-3-carboxylic acid methyl ester (IV) In a reactor under an argon atmosphere, methyl 5-bromo-1H-pyrrole-3-carboxylate (1 equivalent, 5 g, 24.51 mmol), 1-(benzenesulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1 equivalent, 9.41 g, 24.51 mmol), Na2CO3 (3 equivalent, 7.79 g, 73.53 mmol), degassed 1,4-dioxane (25 ml), and degassed distilled water (6.25 ml) were added. After three vacuum / argon cycles, a catalyst complexed with dichloromethane, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.1 equivalent, 2 g, 2.45 mmol), was added. After three vacuum / argon cycles, the reaction mixture was heated at T=100°C for 30 minutes. Distilled water was added, and the product was extracted with AcOEt (3 times). The organic layer was washed with distilled water and brine, dried over anhydrous Na₂SO₄, and evaporated to dryness. The crude product was purified by rapid chromatography (DCM / acetone 95 / 5-9 / 1) to provide the title compound (solid, 4.58 g, Y=49%).

[0118] 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.75 (s, 3 H) 7.14 (s, 1 H) 7.16 (d, J =4.12 Hz, 1 H) 7.52 (d, J =5.19 Hz, 1 H) 7.60 - 7.65 (m, 2 H) 7.70 (s, 1 H)7.71 - 7.75 (m, 1 H) 7.97 (d, J =4.27 Hz, 1 H) 8.09 - 8.16 (m, 2 H) 8.35 (d, J =5.19 Hz, 1 H) 12.30 (br. s., 1 H). LCMS: m / z 382[M+H] + HRMS (ESI) for C 19 H 15 N3O4S[M+H] + The calculated value is 382.0856, and the measured value is 382.0855. Step 2 Methyl 2-bromo-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylate (V) At T=0 °C, 0.33 equivalents of N-bromosuccinimide (566.3 mg, 3.18 mmol) were added to a solution of methyl 5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylate (1 equivalent, 4 g, 10.499 mmol) in MeOH (410 mL) and THF (205 mL). The reaction mixture was stirred at T=0 °C for 30 minutes, and then 0.33 equivalents of N-bromosuccinimide (566.3 mg, 3.18 mmol) were added. The reaction mixture was stirred at T=0 °C for 30 minutes, and then the last portion of N-bromosuccinimide (0.33 equivalents, 566.3 mg, 3.18 mmol) was added. The reaction mixture was stirred at T=0 °C for 1 hour and 30 minutes. Distilled water was added, and the product was extracted three times with AcOEt. The organic layer was washed with brine, dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by rapid chromatography (DCM / acetone 99 / 1-9 / 1) to provide the title compound (white solid, 3.62 g, Y=75%).

[0119] 1 H NMR (500 MHz, DMSO-d6) δ ppm 3.76 (s, 3 H) 7.10 (d, J=4.12 Hz, 1H) 7.15 (s, 1 H) 7.53 (d, J=5.19 Hz, 1 H) 7.60 - 7.66 (m, 2 H) 7.70 - 7.75 (m, 1 H) 7.97 (d, J=4.12 Hz, 1 H) 8.11 - 8.15 (m, 2 H) 8.36 (d, J=5.19 Hz, 1H) 12.93 (s, 1 H). LCMS: m / z 459[M+H] + HRMS (ESI) for C 19 H 14 BrN3O4S [M+H] + The calculated value is 459.9961, and the measured value is 459.996. Step 3 2-(3-chloro-2-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrolo-3-carboxylic acid methyl ester [(VII)] In a reactor under an argon atmosphere, methyl 2-bromo-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylate (1 equivalent, 150 mg, 0.33 mmol), (3-chloro-2-fluorophenyl)boronic acid (1.2 equivalent, 68 mg, 0.39 mmol), Na₂CO₃ (3 equivalent, 103.7 mg, 0.978 mmol), degassed 1,4-dioxane (4 ml), and degassed distilled water (1 ml). After three vacuum / argon cycles, a catalyst complexed with dichloromethane, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.1 equivalent, 26.6 mg, 0.033 mmol), was added. After three vacuum / argon cycles, the reaction mixture was heated at T=100 °C for 2 hours and 30 minutes. Distilled water was added, and the product was extracted with AcOEt (3 times). The organic layer was washed with distilled water and brine, dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by rapid chromatography (DCM / acetone 98 / 2) to provide the title compound (solid, 115 mg, Y=69%).

[0120] 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.66 (s, 3 H) 7.17 (d, J=4.27 Hz, 1 H)7.23 (s, 1 H) 7.34 (t, J=7.85 Hz, 1 H) 7.53 - 7.60 (m, 2 H) 7.61 - 7.66 (m, 2H) 7.67 - 7.71 (m, 1 H) 7.71 - 7.76 (m, 1 H) 8.00 (d, J=4.12 Hz, 1 H) 8.12 -8.15 (m, 2 H) 8.37 (d, J=5.19 Hz, 1 H) 12.49 (s, 1 H). LCMS: m / z 510 [M+H] + HRMS (ESI) corresponds to C 25 H 17 ClFN3O4S [M+H] + The calculated value is 510.0685, and the measured value is 510.0681. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(2-fluoro-4-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.39 (s, 3 H) 3.63 (s, 3 H) 7.08 -7.17 (m, 3 H) 7.20 (d, J =1.37 Hz, 1 H) 7.44 (t, J =7.78 Hz, 1 H) 7.58 (d, J =5.19 Hz, 1 H) 7.63 (t, J =1.00 Hz, 2 H) 7.73 (t, J =1.00 Hz, 1 H) 7.98 (d, J =4.12 Hz, 1 H) 8.11 - 8.17 (m, 2 H) 8.35 (d, J =5.19 Hz, 1H) 12.32 (br. s., 1H). LCMS: m / z 490 [M+H] + HRMS (ESI) for C 26 H 20 FN3O4S [M+H] + The calculated value is 490.1232, and the measured value is 490.1209. 2-(4-chloro-2-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.65 (s, 3 H) 7.16 (d, J=4.12 Hz, 1 H)7.22 (d, J=2.59 Hz, 1 H) 7.42 (dd, J=8.31, 2.06 Hz, 1 H) 7.55 - 7.59 (m, 2 H)7.61 - 7.67 (m, 3 H) 7.72 (d, J=7.47 Hz, 1 H) 7.99 (d, J=4.12 Hz, 1 H) 8.14 (dd, J=8.46, 1.14 Hz, 2 H) 8.37 (d, J=5.19 Hz, 1 H) 12.43 (d, J=1.52 Hz, 1H). LCMS: m / z 510 [M+H] +HRMS (ESI) for C 25 H 17 ClFN3O4S [M+H] + The calculated value is 510.0685, and the measured value is 510.067. 2-(2-chloro-4-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.61 (s, 3 H) 7.16 - 7.19 (m, 1 H)7.22 (d, J=2.75 Hz, 1 H) 7.33 (td, J=8.54, 2.59 Hz, 1 H) 7.56 (d, J=5.19 Hz,1 H) 7.58 - 7.67 (m, 4 H) 7.71 - 7.75 (m, 1 H) 7.99 (d, J=4.12 Hz, 1 H) 8.10- 8.16 (m, 2 H) 8.35 (d, J=5.18 Hz, 1 H) 12.42 (d, J=1.98 Hz, 1 H). LCMS: m / z510[M+H] + HRMS (ESI) for C 25 H 17 ClFN3O4S [M+H] + The calculated value is 510.0685, and the measured value is 510.0689. 2-(2,4-Difluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.65 (s, 3 H) 7.17 (d, J =4.12 Hz, 1 H)7.19 - 7.25 (m, 2 H) 7.39 (td, J =9.84, 2.29 Hz, 1 H) 7.58 (d, J=5.19 Hz, 1 H)7.61 - 7.67 (m, 3 H) 7.71 - 7.75 (m, 1 H) 7.99 (d, J =4.12 Hz, 1 H) 8.14 (d, J =7.47 Hz, 2 H) 8.37 (d, J =5.19 Hz, 1 H) 12.41 (br. s., 1 H). LCMS: m / z 494 [M+H] + HRMS (ESI) for C 25 H 17 F2N3O4S [M+H] + The calculated value is 494.0981, and the measured value is 494.0977. 2-[2-chloro-4-(trifluoromethyl)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.62 (s, 3 H) 7.19 (d, J =3.78 Hz, 1 H)7.24 (s, 1 H) 7.55 (d, J =5.25 Hz, 1 H) 7.60 - 7.67 (m, 2 H) 7.71 - 7.75 (m, 1H) 7.77 - 7.85 (m, 2 H) 7.99 (d, J =3.78 Hz, 1 H) 8.01 (s, 1 H) 8.13 (d, J =7.69 Hz, 2 H) 8.36 (d, J =5.13 Hz, 1 H) 12.48 (br. s., 1 H). LCMS: m / z 560 [M+H] + HRMS (ESI) for C 26 H 17 ClF3N3O4S [M+H] + The calculated value is 560.0653, and the measured value is 560.0656. 2-(2,3-Difluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.66 (s, 3 H) 7.17 (d, J=4.12 Hz, 1 H)7.23 (d, J=1.22 Hz, 1 H) 7.33 (dd, J=7.78, 5.03 Hz, 1 H) 7.39 - 7.44 (m, 1 H)7.51 - 7.57 (m, 1 H) 7.59 (d, J=5.34 Hz, 1 H) 7.61 - 7.67 (m, 2 H) 7.71 -7.76 (m, 1 H) 8.00 (d, J=4.12 Hz, 1 H) 8.14 (dd, J=8.46, 1.14 Hz, 2 H) 8.38(d, J=5.19 Hz, 1 H) 12.49 (s, 1 H). LCMS: m / z 494 [M+H] + HRMS (ESI) for C 25 H 17 F2N3O4S [M+H] + The calculated value is 494.0981, and the measured value is 494.0981. 2-(2,3-Dichlorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.62 (s, 3 H) 7.18 (d, J=4.27 Hz, 1H) 7.22 (s, 1 H) 7.43 - 7.48 (m, 1 H) 7.50 - 7.53 (m, 1 H) 7.55 (d, J=5.19Hz, 1 H) 7.60 - 7.67 (m, 2 H) 7.70 - 7.78 (m, 2 H) 7.99 (d, J=4.12 Hz, 1 H)8.11 - 8.16 (m, 2 H) 8.36 (d, J=5.19 Hz, 1 H) 12.47 (s, 1 H). LCMS: m / z 526 [M+H] + HRMS (ESI) for C 25 H 17Cl2N3O4S [M+H] + The calculated value is 526.039, and the measured value is 526.0383. 2-[4-methyl-2-(trifluoromethyl)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.47 (s, 3 H) 3.54 (s, 3 H) 7.16 (d, J=4.12 Hz, 1 H) 7.19 (d, J=2.75 Hz, 1 H) 7.44 (d, J=7.78 Hz, 1 H) 7.52 (d, J=5.34 Hz, 1 H) 7.55 (d, J=7.63 Hz, 1 H) 7.60 - 7.65 (m, 2 H) 7.68 (s, 1 H)7.70 - 7.75 (m, 1 H) 7.98 (d, J=4.12 Hz, 1 H) 8.10 - 8.14 (m, 2 H) 8.33 (d, J=5.19 Hz, 1H) 12.39 (d, J=2.14 Hz, 1H). LCMS: m / z 540 [M+H] + HRMS (ESI) for C 27 H 20 F3N3O4S [M+H] + The calculated value is 540.1199, and the measured value is 540.1193. 2-(2-chloro-4-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d6) δ ppm 2.38 (s, 3 H) 3.60 (s, 3 H) 7.16 (d, J=4.12 Hz, 1 H) 7.20 (d, J=2.90 Hz, 1 H) 7.24 (dd, J=7.78, 0.76 Hz, 1 H) 7.39(s, 2 H) 7.56 (d, J=5.19 Hz, 1 H) 7.61 - 7.66 (m, 2 H) 7.71 - 7.76 (m, 1 H)7.98 (d, J=4.12 Hz, 1 H) 8.10 - 8.16 (m, 2 H) 8.34 (d, J=5.34 Hz, 1 H) 12.34(d, J=2.29 Hz, 1 H). LCMS: m / z 506 [M+H] + HRMS (ESI) for C 26 H 20 ClN3O4S [M+H] + The calculated value is 506.0936, and the measured value is 506.0938. 2-(2,3-Difluoro-4-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.36 (d, J=1.53 Hz, 3 H) 3.66 (s, 3 H)7.16 (d, J=4.12 Hz, 1 H) 7.18 - 7.21 (m, 1 H) 7.22 (d, J=2.75 Hz, 1 H) 7.27 -7.32 (m, 1 H) 7.59 (d, J=5.34 Hz, 1 H) 7.62 - 7.67 (m, 2 H) 7.70 - 7.76 (m, 1H) 7.99 (d, J=4.12 Hz, 1 H) 8.14 (dd, J=8.46, 1.14 Hz, 2 H) 8.37 (d, J=5.18Hz, 1H) 12.43 (d, J=2.14 Hz, 1H). LCMS: m / z 508 [M+H] + HRMS (ESI) for C 26 H 19 F2N3O4S [M+H] +The calculated value is 508.1137, and the measured value is 508.1132. 2-[2-methyl-4-(trifluoromethyl)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.25 (s, 3 H) 3.62 (s, 3 H) 7.18 (d, J=4.27 Hz, 1 H) 7.25 (s, 1 H) 7.52 - 7.58 (m, 2 H) 7.63 (t, J=7.93 Hz, 3 H)7.69 - 7.76 (m, 2 H) 7.99 (d, J=4.12 Hz, 1 H) 8.13 (dd, J=8.54, 1.07 Hz, 2 H) 8.34 (d, J=5.19 Hz, 1 H) 12.36 (s, 1 H). LCMS: m / z 540 [M+H] + HRMS (ESI) for C 27 H 20 F3N3O4S [M+H] + The calculated value is 540.12, and the measured value is 540.1207. 2-(2-fluoro-3-methoxyphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrolo-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d6) δ ppm 3.64 (s, 3 H) 3.88 (s, 3 H) 7.10 (td,J=6.83, 1.75 Hz, 1 H) 7.16 (d, J=4.12 Hz, 1 H) 7.18 - 7.30 (m, 3 H) 7.59 (d,J=5.19 Hz, 1 H) 7.60 - 7.67 (m, 2 H) 7.71 - 7.77 (m, 1 H) 7.98 (d, J=4.12 Hz,1 H) 8.13 (dd, J=8.46, 0.99 Hz, 2 H) 8.36 (d, J=5.19 Hz, 1 H) 12.39 (br. s.,1 H). LCMS: m / z 506 [M+H] + HRMS (ESI) for C 26 H 20 FN3O5S [M+H] + The calculated value is 506.1181, and the measured value is 506.1177. 2-(2-chloro-3-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrolo-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.61 (s, 3 H) 7.17 (d, J=4.12 Hz, 1 H)7.22 (s, 1 H) 7.39 (d, J=7.02 Hz, 1 H) 7.44 - 7.50 (m, 1 H) 7.50 - 7.54 (m, 1H) 7.55 (d, J=5.19 Hz, 1 H) 7.60 - 7.66 (m, 2 H) 7.70 - 7.75 (m, 1 H) 7.99(d, J=4.12 Hz, 1 H) 8.12 (dd, J=8.46, 1.14 Hz, 2 H) 8.35 (d, J=5.34 Hz, 1 H)12.48 (br. s., 1 H). LCMS: m / z 510 [M+H] + HRMS (ESI) for C 25 H 17 ClFN3O4S [M+H] + The calculated value is 510.0685, and the measured value is 510.0686. 2-(2-fluoro-3-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrolo-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.30 (d, J =1.59 Hz, 3 H) 3.64 (s, 3 H)7.09 - 7.24 (m, 3 H) 7.37 (t, J =7.26 Hz, 2 H) 7.59 (d, J =5.25 Hz, 1 H) 7.61 -7.66 (m, 2 H) 7.70 - 7.76 (m, 1 H) 7.98 (d, J =4.15 Hz, 1 H) 8.11 - 8.16 (m, 2H) 8.35 (d, J =5.13 Hz, 1 H) 12.34 (br. s., 1 H). LCMS: m / z 490 [M+H] + HRMS (ESI) for C 26 H 20 FN3O4S [M+H] + The calculated value is 490.1232, and the measured value is 490.1225. 2-[2-methyl-3-(trifluoromethyl)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d6) δ ppm 2.25 (s, 3 H) 3.61 (s, 3 H) 7.17 -7.20 (m, 1 H) 7.24 - 7.26 (m, 1 H) 7.44 - 7.51 (m, 1 H) 7.55 - 7.58 (m, 1 H)7.60 - 7.67 (m, 3 H) 7.70 - 7.75 (m, 1 H) 7.78 - 7.82 (m, 1 H) 7.98 - 8.00 (m, 1 H) 8.10 - 8.15 (m, 2 H) 8.31 - 8.36 (m, 1 H) 12.38 (d, J=2.29 Hz, 1 H). LCMS: m / z 540 [M+H] + HRMS (ESI) for C 27 H 20 F3N3O4S [M+H] + The calculated value is 540.11994, and the measured value is 540.1203. 2-[4-methoxy-2-(trifluoromethyl)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.55 (s, 3 H) 3.90 (s, 3 H) 7.15 (d, J=4.12 Hz, 1 H) 7.19 (d, J=2.75 Hz, 1 H) 7.30 (dd, J=8.46, 2.52 Hz, 1 H) 7.33(d, J=2.59 Hz, 1 H) 7.47 - 7.50 (m, 1 H) 7.52 (d, J=5.19 Hz, 1 H) 7.61 - 7.66(m, 2 H) 7.71 - 7.75 (m, 1 H) 7.98 (d, J=4.12 Hz, 1 H) 8.09 - 8.14 (m, 2 H)8.33 (d, J=5.34 Hz, 1 H) 12.37 (d, J=2.29 Hz, 1 H). LCMS: m / z 556 [M+H] + HRMS (ESI) for C 27 H 20 F3N3O5S [M+H] +The calculated value is 556.1149, and the measured value is 556.1144. 2-[2-chloro-4-(difluoromethoxy)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.94 (s, 3 H) 7.18 (d, J=4.12 Hz, 1 H)7.22 (d, J=2.75 Hz, 1 H) 7.27 (dd, J=8.35, 2.52 Hz, 1 H) 7.48 (d, J=2.59 Hz,1 H) 7.55 - 7.56 (m, 1 H) 7.63 - 7.65 (m, 2 H) 7.71 - 7.74 (m, 1 H) 7.98 (d,J=4.10 Hz, 1 H) 8.12 - 8.14 (m, 2 H) 8.35 (d, J=5.31 Hz, 1 H) 12.42 (d, J=2.24 Hz, 1H). LCMS: m / z 558 [M+H] + HRMS (ESI) for C 26 H 18 ClF2N3O5S [M+H] + The calculated value is 558.0697, and the measured value is 558.0714. 2-(3,4-Dichlorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrolo-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d6) δ ppm 3.71 (s, 3 H) 7.15 (d, J=4.12 Hz, 1 H)7.21 (d, J=2.59 Hz, 1 H) 7.61 - 7.66 (m, 3 H) 7.66 - 7.70 (m, 1 H) 7.71 -7.76 (m, 2 H) 7.94 - 8.02 (m, 2 H) 8.14 (dd, J=8.39, 1.07 Hz, 2 H) 8.39 (d, J=5.19 Hz, 1 H) 12.32 (d, J=1.98 Hz, 1 H). LCMS: m / z 526 [M+H] + HRMS (ESI) for C 25 H 17 Cl2N3O4S [M+H] + The calculated value is 526.039, and the measured value is 526.0387. 2-(3,4-Difluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.70 (s, 3 H) 7.15 (d, J=4.12 Hz, 1 H)7.20 (s, 1 H) 7.53 - 7.57 (m, 1 H) 7.62 - 7.67 (m, 3 H) 7.70 - 7.76 (m, 1 H)7.77 - 7.84 (m, 1 H) 7.99 (d, J=4.12 Hz, 1 H) 8.12 - 8.16 (m, 2 H) 8.38 (d, J=5.19 Hz, 1 H) 12.27 (s, 1 H). LCMS: m / z 494 [M+H] + HRMS (ESI) for C 25 H 17 F2N3O4S [M+H] + The calculated value is 494.0981, and the measured value is 494.0982. 2-(3-ethoxy-2-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 1.37 (t, J=6.94 Hz, 1 H) 3.65 (s, 3 H)4.15 (q, J=6.91 Hz, 1 H) 7.08 (td, J=6.90, 1.60 Hz, 1 H) 7.16 (d, J=4.27 Hz, 1 H) 7.17 - 7.22 (m, 2 H) 7.22 - 7.27 (m, 1 H) 7.59 (d, J=5.19 Hz, 1 H) 7.61- 7.67 (m, 2 H) 7.70 - 7.76 (m, 1 H) 7.99 (d, J=4.12 Hz, 1 H) 8.13 (dd, J=8.39, 1.07 Hz, 2 H) 8.36 (d, J=5.19 Hz, 1 H) 12.38 (d, J=2.14 Hz, 1 H). LCMS: m / z 520 [M+H] + HRMS (ESI) for C 27 H 22 FN3O5S [M+H] + The calculated value is 520.1337, and the measured value is 520.1335. 2-(4-methyl-3-nitrophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.58 (s, 3 H) 3.69 - 3.72 (m, 3 H)7.16 (d, J=4.12 Hz, 1 H) 7.23 (s, 1 H) 7.57 - 7.68 (m, 4 H) 7.70 - 7.77 (m, 1H) 7.94 (dd, J=7.93, 1.83 Hz, 1 H) 8.00 (d, J=4.12 Hz, 1 H) 8.12 - 8.18 (m, 2H) 8.32 (d, J=1.68 Hz, 1 H) 8.39 (d, J=5.18 Hz, 1 H) 12.36 (s, 1 H). LCMS: m / z517 [M+H] + HRMS (ESI) for C 26 H20 N4O6S [M+H] + The calculated value is 517.1177, and the measured value is 517.118. 2-(3-cyano-4-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.70 (s, 3 H) 7.17 (d, J=4.12 Hz, 1 H)7.21 (d, J=2.75 Hz, 1 H) 7.61 - 7.69 (m, 4 H) 7.72 - 7.77 (m, 1 H) 8.00 (d, J=4.12 Hz, 1 H) 8.06 - 8.18 (m, 3 H) 8.27 (dd, J=6.18, 2.36 Hz, 1 H) 8.39 (d, J=5.19 Hz, 1 H) 12.35 (d, J=2.14 Hz, 1 H). LCMS: m / z 501 [M+H] + HRMS (ESI) for C 26 H 17 FN4O4S [M+H] + The calculated value is 501.1028, and the measured value is 501.102. 2-(dibenzo[b,d]thiophene-4-yl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d6) δ ppm 3.51 - 3.60 (m, 3 H) 7.23 (d, J=4.27Hz, 1 H) 7.31 (d, J=2.59 Hz, 1 H) 7.51 - 7.56 (m, 2 H) 7.59 - 7.68 (m, 5 H)7.69 - 7.77 (m, 1 H) 7.94 - 8.05 (m, 2 H) 8.09 - 8.17 (m, 2 H) 8.37 (d, J=5.19 Hz, 1 H) 8.40 - 8.51 (m, 2 H) 12.60 (d, J=2.14 Hz, 1 H). LCMS: m / z 564 [M+H] + HRMS (ESI) for C 31 H 21 N3O4S2[M+H] + The calculated value is 564.1046, and the measured value is 564.1054. 2-(4-methylnaphthyl-1-yl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.74 (s, 3 H) 3.49 (s, 3 H) 7.21 (d, J=4.27 Hz, 1 H) 7.32 (d, J=2.90 Hz, 1 H) 7.42 - 7.52 (m, 3 H) 7.55 - 7.68 (m,5 H) 7.71 - 7.78 (m, 1 H) 7.99 (d, J=4.12 Hz, 1 H) 8.07 - 8.17 (m, 3H) 8.33 (d, J=5.19 Hz, 1 H) 12.44 (d, J=2.14 Hz, 1 H). LCMS: m / z 522 [M+H] + HRMS (ESI) for C 30 H 23 N3O4S [M+H] + The calculated value is 522.1482, and the measured value is 522.1477. 2-(3-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1H NMR (500 MHz, DMSO-d6) δ ppm 3.70 (s, 3 H) 7.15 (d, J=4.27 Hz, 1 H) 7.21 (d, J=2.75 Hz, 1 H) 7.23-7.30 (m, 1 H) 7.44-7.56 (m, 3 H) 7.60-7.68 (m, 3 H) 7.73 (d, J=7.47 Hz, 1 H) 7.99 (d, J=4.27 Hz, 1 H) 8.04-8.17 (m, 2 H) 8.37 (d, J=5.34 Hz, 1 H) 12.26 (d, J=2.14 Hz, 1 H). LCMS: m / z 476 [M+H] + HRMS (ESI) for C 25 H 18 FN3O4S [M+H] + The calculated value is 476.1075, and the measured value is 476.1072. 5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2-[4-(trifluoromethoxy)phenyl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO-d6) δ ppm 3.69 (s, 3 H) 7.16 (d, J=4.12 Hz, 1H) 7.21 (d, J=2.75 Hz, 1 H) 7.47 (d, J=8.08 Hz, 2 H) 7.57 - 7.67 (m, 3 H)7.70 - 7.76 (m, 1 H) 7.77 - 7.84 (m, 2 H) 7.99 (s, 1 H) 8.07 - 8.18 (m, 2 H)8.37 (d, J=5.19 Hz, 1 H) 12.28 (d, J=2.29 Hz, 1 H). LCMS: m / z 542 [M+H] + HRMS (ESI) for C 26 H 18 F3N3O5S [M+H] + The calculated value is 542.0992, and the measured value is 542.0999. 2-(1-benzothiophene-3-yl)-5-[1-(benzenesulfonyl)-1 H -pyrrolo[2,3- b ]pyridin-4-yl]-1H methyl pyrrole-3-carboxylate (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.57 (s, 3 H) 7.20 (d, J =4.12 Hz, 1 H)7.29 (d, J =2.59 Hz, 1 H) 7.37 - 7.45 (m, 2 H) 7.57 (m, J =1.98 Hz, 1 H) 7.64(m, J =5.19 Hz, 3 H) 7.73 (tt, J =7.50, 1.40 Hz, 1 H) 8.00 (m, J =4.12 Hz, 2 H)8.07 (m, J =1.83 Hz, 1 H) 8.14 (m, J =8.46, 1.14 Hz, 2 H) 8.36 (d, J =5.34 Hz, 1H) 12.45 (d, J =1.83 Hz, 1 H). LCMS: m / z 514 [M+H] + HRMS (ESI) for C 27 H 19 N3O4S2[M+H] + The calculated value is 514.089, and the measured value is 514.0878. 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[1-(benzenesulfonyl)-1 H -pyrrolo[2,3- b ]pyridin-4-yl] -1H methyl pyrrole-3-carboxylate (VII) 1H NMR (500 MHz, DMSO-d6) δ ppm 3.68 (s, 3 H) 4.22 - 4.35 (m, 4 H)6.93 (d, J=8.39 Hz, 1 H) 7.12 (d, J=4.12 Hz, 1 H) 7.13 - 7.18 (m, 2 H) 7.20(d, J=2.14 Hz, 1 H) 7.58 - 7.68 (m, 3 H) 7.69 - 7.76 (m, 1 H) 7.97 (d, J=4.12Hz, 1 H) 8.13 (dd, J=8.46, 0.99 Hz, 2 H) 8.34 (d, J=5.19 Hz, 1 H) 12.06 (s, 1H). LCMS: m / z 516 [M+H] + HRMS (ESI) for C 27 H 21 N3O6S [M+H] + The calculated value is 516.1224, and the measured value is 516.1206. 2-(4-fluoro-2-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.16 (s, 1 H) 3.61 (s, 3 H) 7.10 (td, J =8.50, 2.67 Hz, 1 H) 7.16 (d, J =4.12 Hz, 1 H) 7.18 - 7.22 (m, 2 H) 7.36 (dd, J =8.39, 6.10 Hz, 1 H) 7.57 (d, J =5.19 Hz, 1 H) 7.61 - 7.65 (m, 2 H) 7.70 -7.75 (m, 1 H) 7.97 (d, J =4.12 Hz, 1 H) 8.11 - 8.13 (m, 2 H) 8.33 (d, J =5.19Hz, 1H) 12.26 (br. s., 1H). LCMS: m / z 490 [M+H] + HRMS (ESI) for C26 H 20 FN3O4S [M+H] + The calculated value is 490.1232, and the measured value is 490.1224. Transformation 1 2-(2-fluoro-4-methylphenyl)-4-iodo-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) To a solution of methyl 2-(2-fluoro-4-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylate (1 equivalent, 200 mg, 0.40 mmol) in DMF (2 mL), N-iodosuccinimide (1.15 equivalent, 106 mg, 0.47 mmol) was added. The reaction mixture was stirred at room temperature for 15 h. Ice and distilled water were added and precipitate formation was observed. The solid was filtered and washed three times with distilled water and three times with Et₂O to give the title compound (beige solid, 960 mg, Y = quantitative %).

[0121] 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.36 (s, 3 H) 3.58 (s, 3 H) 6.84 (d, J =3.81 Hz, 1 H) 7.05 - 7.16 (m, 2 H) 7.45 (t, J =8.01 Hz, 1 H) 7.48 - 7.53 (m,1 H) 7.60 - 7.69 (m, 2 H) 7.70 - 7.77 (m, 1 H) 8.00 (d, J =4.12 Hz, 1 H) 8.10- 8.21 (m, 2 H) 8.46 (d, J =4.88 Hz, 1 H) 12.49 (br. s., 1 H). LCMS: m / z 616 [M+H] + HRMS (ESI) for C 26 H 19 FIN3O4S [M+H] + The calculated value is 616.0198, and the measured value is 616.0182. 2-(2-fluoro-4-methylphenyl)-4-bromo-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylic acid methyl ester (VII) At T=0 °C, 0.33 equivalents of N-bromosuccinimide (36 mg, 0.3 mmol) were added to a solution of methyl 2-(2-fluoro-4-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylate (1 equivalent, 300 mg, 0.61 mmol) in MeOH (24.4 mL) and THF (6.1 mL). The reaction mixture was stirred at T=0 °C for 30 minutes, and then 0.33 equivalents of N-bromosuccinimide (36 mg, 0.3 mmol) were added. The reaction mixture was stirred at T=0 °C for 30 minutes, and then the final portion of N-bromosuccinimide (0.33 equivalents, 36 mg, 0.3 mmol) was added. The reaction mixture was stirred at T=0 °C for 1 hour and 30 minutes. Distilled water was added, and the product was extracted three times with AcOEt. The organic layer was washed with brine, dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by rapid chromatography (hexane / AcOEt6 / 4) to provide the title compound (white solid, 188 mg, Y=54%).

[0122] LCMS: m / z 568 [M+H] + HRMS (ESI) for C 26 H 19 BrFN3O4S [M+H] + The calculated value is 568.0336, and the measured value is 568.0331. Step 4 2-(3-Chloro-2-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) At T=0°C, methyl 2-(3-chloro-2-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylate (1 equivalent, 100 mg, 0.196 mmol) in dry THF (1 ml) was added to a solution of methyl 2-(3-chloro-2-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrrole-3-carboxylate (1 equivalent, 100 mg, 0.196 mmol) in mineral oil. The reaction mixture was stirred at T=0°C for 20 minutes, and SEMCl (1.8 equivalent, 63 mg, 100 mg, 0.33 mmol) was added. L, 0.35 mmol). After 10 minutes at T=0℃, the reaction was heated and stirred at room temperature for 3 hours. Distilled water was added, and the product was extracted with AcOEt. The organic layer was washed with distilled water and brine, dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by rapid chromatography (hexane / AcOEt 85 / 15-7 / 3) to provide the title compound (solid, 118 mg, Y=94%).

[0123] 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.34 - -0.21 (m, 9 H) 0.40 - 0.59 (m,2 H) 2.89 - 2.98 (m, 2 H) 3.62 (s, 3 H) 4.96 - 5.21 (m, 2 H) 6.90 (d, J=4.12Hz, 1 H) 6.92 (s, 1 H) 7.36 (t, J=7.93 Hz, 1 H) 7.50 (d, J=5.03 Hz, 1 H) 7.52- 7.56 (m, 1 H) 7.62 - 7.68 (m, 2 H) 7.71 - 7.77 (m, 2 H) 8.01 (d, J=3.97 Hz,1 H) 8.17 (dd, J=8.46, 1.14 Hz, 2 H) 8.45 (d, J=5.03 Hz, 1 H). LCMS: m / z 640[M+H] + HRMS (ESI) for C 31 H 31 ClFN3O5SSi [M+H] + The calculated value is 640.1499, and the measured value is 640.149. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(2-fluoro-4-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.33 - -0.26 (m, 9 H) 0.47 (t, J=8.31Hz, 1 H) 2.40 (s, 3 H) 2.93 (q, J=8.29 Hz, 1 H) 3.60 (s, 3 H) 4.98 - 5.18 (m,2 H) 6.87 - 6.94 (m, 2 H) 7.11 - 7.19 (m, 2 H) 7.36 - 7.41 (m, 1 H) 7.51 (d,J=5.19 Hz, 1 H) 7.62 - 7.68 (m, 2 H) 7.71 - 7.79 (m, 1 H) 8.00 (d, J=4.12 Hz,1 H) 8.13 - 8.22 (m, 2 H) 8.44 (d, J=5.03 Hz, 1 H). LCMS: m / z 620 [M+H] + HRMS (ESI) for C 32 H 34 FN3O5SSi[M+H] + The calculated value is 620.2045, and the measured value is 620.2047. 2-(4-Chloro-2-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.30 - -0.28 (m, 9 H) 0.44 - 0.50 (m,2 H) 2.91 - 2.97 (m, 2 H) 3.59 - 3.64 (m, 3 H) 5.00 - 5.18 (m, 2 H) 6.89 (d,J=4.12 Hz, 1 H) 6.91 (s, 1 H) 7.44 (dd, J=8.24, 1.98 Hz, 1 H) 7.47 - 7.51 (m,1 H) 7.57 - 7.62 (m, 2 H) 7.63 - 7.67 (m, 2 H) 7.73 - 7.77 (m, 1 H) 8.01 (d,J=3.97 Hz, 1 H) 8.17 (dd, J=8.46, 1.14 Hz, 2 H) 8.45 (d, J=5.19 Hz, 1 H). LCMS: m / z 640 [M+H] + HRMS (ESI) for C 31 H 31 ClFN3O5SSi [M+H] + The calculated value is 640.1499, and the measured value is 640.1. 2-(2-Chloro-4-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.31 - -0.27 (m, 9 H) 0.47 (dd, J=9.38, 6.94 Hz, 2 H) 2.93 (dd, J=9.23, 7.55 Hz, 2 H) 3.59 (s, 3 H) 4.93 (d, J=11.13 Hz, 1 H) 5.10 (d, J=11.13 Hz, 1 H) 6.86 (d, J=4.12 Hz, 1 H) 6.89 (s, 1H) 7.36 (td, J=8.46, 2.59 Hz, 1 H) 7.48 (d, J=5.19 Hz, 1 H) 7.60 (dd, J=8.62,6.18 Hz, 1H) 7.62 - 7.68 (m, 3 H) 7.71 - 7.77 (m, 1 H) 8.01 (d, J=4.12 Hz, 1H) 8.16 (dd, J=8.46, 1.14 Hz, 2 H) 8.44 (d, J=5.03 Hz, 1 H). LCMS: m / z 640 [M+H] + HRMS (ESI) for C 31 H 31 ClFN3O5SSi [M+H] + The calculated value is 640.1499, and the measured value is 640.1491. 2-(2,4-Difluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 624 [M+H] + HRMS (ESI) for C 31 H 31 F2N3O5SSi [M+H] + The calculated value is 624.1795, and the measured value is 624.1788. 2-[2-chloro-4-(trifluoromethyl)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.32 - -0.30 (m, 8 H) 0.40 - 0.48 (m,2 H) 2.87 - 2.95 (m, 2 H) 3.57 - 3.62 (m, 3 H) 4.93 - 5.14 (m, 2 H) 6.87 (d,J=4.12 Hz, 1 H) 6.92 (s, 1 H) 7.45 - 7.51 (m, 1 H) 7.62 - 7.68 (m, 2 H) 7.72- 7.77 (m, 1 H) 7.79 - 7.82 (m, 1 H) 7.84 - 7.88 (m, 1 H) 8.02 (d, J=4.12 Hz,1 H) 8.05 (d, J=0.76 Hz, 1 H) 8.17 (dd, J=8.54, 1.07 Hz, 2 H) 8.46 (d, J=5.19Hz, 1 H). LCMS: m / z 690 [m+H] + HRMS (ESI) for C 32 H 31 ClF3N3O5SSi [M+H] + The calculated value is 690.1467, and the measured value is 690.1469. 2-(2,3-Difluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 624 [M+H] + HRMS (ESI) for C 31 H 31 F2N3O5SSi [M+H] + The calculated value is 624.1795, and the measured value is 624.1791. 2-(2,3-Dichlorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 656 [M+H] + HRMS (ESI) for C 31 H 31 Cl2N3O5SSi [M+H] +The calculated value is 656.1204, and the measured value is 656.1207. 2-[4-methyl-2-(trifluoromethyl)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.33 - -0.29 (m, 9 H) 0.45 (dd, J=9.23, 7.55 Hz, 2 H) 2.48 (s, 3 H) 2.90 (dd, J=9.30, 7.47 Hz, 2 H) 3.51 - 3.53(m, 3 H) 4.75 (d, J=10.98 Hz, 1 H) 5.07 (d, J=10.98 Hz, 1 H) 6.77 (d, J=4.12Hz, 1 H) 6.85 (s, 1 H) 7.39 - 7.45 (m, 2 H) 7.58 (d, J=7.93 Hz, 1 H) 7.62 -7.67 (m, 2 H) 7.70 (s, 1 H) 7.72 - 7.76 (m, 1 H) 8.01 (d, J=3.97 Hz, 1 H)8.16 (dd, J=8.62, 1.14 Hz, 2 H) 8.44 (d, J=5.03 Hz, 1 H). LCMS: m / z 670 [m+H] + HRMS (ESI) for C 33 H 34 F3N3O5SSi [M+H] + The calculated value is 670.2014, and the measured value is 670.2007. 2-(2-Chloro-4-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 636 [M+H] + HRMS (ESI) for C 32 H 34 ClN3O5SSi [M+H] +The calculated value is 636.1750, and the measured value is 636.1753. 2-(2,3-Difluoro-4-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 638 [M+H] + HRMS (ESI) for C 32 H 33 F2N3O5SSi [M+H] + The calculated value is 638.1951, and the measured value is 638.1956. 2-[2-methyl-4-(trifluoromethyl)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 670 [m+H] + HRMS (ESI) for C 33 H 34 F3N3O5SSi [M+H] + The calculated value is 670.2013, and the measured value is 670.2017. 2-(2-fluoro-3-methoxyphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 636 [M+H] + HRMS (ESI) for C 32 H 34 FN3O6SSi [M+H] + The calculated value is 636.1994, and the measured value is 636.1993. 2-(2-Chloro-3-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 640 [M+H] +HRMS (ESI) for C 31 H 31 ClFN3O5SSi [M+H] + The calculated value is 640.1499, and the measured value is 640.1495. 2-(2-fluoro-3-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 620 [M+H] + HRMS (ESI) for C 32 H 34 FN3O5SSi [M+H] + The calculated value is 620.2045, and the measured value is 620.2039. 2-[2-methyl-3-(trifluoromethyl)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 670 [m+H] + HRMS (ESI) for C 33 H 34 F3N3O5SSi [M+H] + The calculated value is 670.2013, and the measured value is 670.2008. 2-[4-methoxy-2-(trifluoromethyl)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 686 [M+H] + HRMS (ESI) for C 33 H 34 F3N3O6SSi [M+H] + The calculated value is 686.1963, and the measured value is 686.1961. 2-[2-chloro-4-(difluoromethoxy)phenyl]-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.31 - -0.28 (m, 9 H) 0.44 - 0.49 (m,2 H) 2.91 - 2.95 (m, 2 H) 3.59 (s, 3 H) 4.42- 5.12 (m, 2 H) 6.85 (d, J=3.85Hz, 1 H) 6.89 (s, 1 H) 7.59 (d, J=3.88 Hz, 1 H) 7.63 - 7.66 (m, 2 H) 7.73 -7.76 (m, 1 H) 8.01 (d, J=4.22 Hz, 1 H) 8.15 - 8.17 (m, 2 H) 8.45 (d, J=5.22Hz, 1H). LCMS: m / z 688 [M+H] + HRMS (ESI) for C 32 H 32 ClF2N3O6SSi [M+H] + The calculated value is 688.1511, and the measured value is 688.1508. 2-(3,4-Dichlorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.27 - -0.24 (m, 8 H) 0.47 - 0.57 (m,2 H) 2.97 - 3.04 (m, 2 H) 3.62 (s, 3 H) 5.05 (s, 2 H) 6.89 (s, 1 H) 6.93 (d,J=3.97 Hz, 1 H) 7.45 - 7.54 (m, 2 H) 7.62 - 7.69 (m, 2 H) 7.71 - 7.78 (m, 2H) 7.81 (d, J=1.98 Hz, 1 H) 8.01 (d, J=4.12 Hz, 1 H) 8.13 - 8.21 (m, 2 H)8.45 (d, J=5.19 Hz, 1 H). LCMS: m / z 656 [M+H] + HRMS (ESI) for C 31 H 31 Cl2N3O5SSi [M+H] + The calculated value is 656.1204, and the measured value is 656.1215. 2-(3,4-Difluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.28 - -0.26 (m, 8 H) 0.48 - 0.56 (m,2 H) 2.96 - 3.03 (m, 2 H) 3.61 (s, 3 H) 5.06 (s, 2 H) 6.88 (s, 1 H) 6.92 (d,J=4.12 Hz, 1 H) 7.34 - 7.39 (m, 1 H) 7.47 - 7.51 (m, 1 H) 7.53 - 7.67 (m, 4H) 7.72 - 7.78 (m, 1 H) 8.01 (d, J=3.97 Hz, 1 H) 8.14 - 8.21 (m, 2 H) 8.45(d, J=5.03 Hz, 1 H). LCMS: m / z 624 [M+H] + HRMS (ESI) for C 31 H 31 F2N3O5SSi [M+H] +The calculated value is 624.1795, and the measured value is 624.1816. 2-(3-ethoxy-2-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.31 - -0.26 (m, 9 H) 0.47 (t, J=8.31 ​​Hz, 2 H) 1.37 (t, J=7.02 Hz, 1 H) 2.87 - 3.02 (m, 2 H) 3.61 (s, 3 H)4.04 - 4.22 (m, 1 H) 4.98 - 5.18 (m, 2 H) 6.84 - 6.94 (m, 1 H) 6.97 - 7.09(m, 2 H) 7.19 - 7.25 (m, 1 H) 7.26 - 7.32 (m, 1 H) 7.52 (d, J=5.03 Hz, 1 H)7.62 - 7.68 (m, 2H) 7.72 - 7.77 (m, 1 H) 8.00 (d, J=4.12 Hz, 1 H) 8.17 (dd,J=8.46, 1.14 Hz, 2 H) 8.44 (d, J=5.19 Hz, 1 H). LCMS: m / z 650 [M+H] + HRMS (ESI) for C 33 H 36 FN3O6SSi [M+H] + The calculated value is 650.2151, and the measured value is 650.2164. 2-(4-Methyl-3-nitrophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.28 - -0.25 (m, 8 H) 0.52 - 0.58 (m,2 H) 2.60 (s, 3 H) 2.98 - 3.05 (m, 2 H) 3.62 (s, 3 H) 5.04 (s, 2 H) 6.91 (s,1 H) 6.93 (d, J=4.12 Hz, 1 H) 7.51 (d, J=5.03 Hz, 1 H) 7.59 - 7.69 (m, 3 H)7.71 - 7.78 (m, 2 H) 8.01 (d, J=4.12 Hz, 1 H) 8.14 - 8.24 (m, 3 H) 8.45 (d, J=5.03 Hz, 1H). LCMS: m / z 647 [M+H] + HRMS (ESI) for C 32 H 34 N4O7SSi [M+H] + The calculated value is 647.1990, and the measured value is 647.2003; 2-(3-Cyano-4-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.28 - -0.24 (m, 9 H) 0.46 - 0.57 (m,2 H) 2.92 - 3.04 (m, 2 H) 3.62 (s, 3 H) 5.05 (s, 2 H) 6.90 (s, 1 H) 6.92 (d, J =4.12 Hz, 1 H) 7.47 (d, J =5.03 Hz, 1 H) 7.62 - 7.71 (m, 3 H) 7.72 - 7.77 (m,1 H) 7.87 - 7.97 (m, 1 H) 8.02 (d, J =4.12 Hz, 1 H) 8.12 (dd, J =6.25, 2.14 Hz,1 H) 8.15 - 8.20 (m, 2 H) 8.46 (d, J=5.03 Hz, 1 H). LCMS: m / z 631[M+H] + HRMS (ESI) for C 32 H 31 FN4O5SSi [M+H] + The calculated value is 631.1841, and the measured value is 631.1846. 2-(dibenzo[b,d]thiophen-4-yl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) LCMS: m / z 694 [M+H] + HRMS (ESI) for C 37 H 35 N3O5S2Si [M+H] + The calculated value is 694.1860, and the measured value is 694.1863. 2-(4-methylnaphthyl-1-yl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.40 - -0.35 (m, 9 H) 0.19 - 0.32 (m,2H) 2.67 - 2.81 (m, 5 H) 3.44 (s, 3 H) 4.74 - 5.08 (m, 2 H) 6.91 - 7.01 (m, 2H) 7.43 - 7.51 (m, 4 H) 7.53 - 7.61 (m, 2 H) 7.62 - 7.71 (m, 2 H) 7.73 - 7.78(m, 1 H) 8.02 (d, J=4.12 Hz, 1 H) 8.10 (d, J=8.39 Hz, 1 H) 8.17 (dd, J=8.46,0.99 Hz, 1 H) 8.44 (d, J=5.03 Hz, 1 H). LCMS: m / z 652[M+H] + HRMS (ESI) for C 36 H 37 N3O5SSi [M+H]+ The calculated value is 652.2296, and the measured value is 652.2303; 2-(3-Fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.29 - -0.24 (m, 9 H) 0.49 - 0.56 (m,2 H) 2.94 - 3.02 (m, 2 H) 3.60 (s, 3 H) 5.05 (s, 2 H) 6.89 (s, 1 H) 6.92 (d, J =3.97 Hz, 1 H) 7.29 - 7.40 (m, 3 H) 7.47 - 7.56 (m, 2 H) 7.60 - 7.68 (m, 2H) 7.70 - 7.77 (m, 1 H) 8.01 (d, J =4.12 Hz, 1 H) 8.17 (dd, J =8.46, 1.14 Hz, 2H) 8.45 (d, J =5.03 Hz, 1 H). LCMS: m / z 606 [M+H] + HRMS (ESI) for C 31 H 32 FN3O5SSi [M+H] + The calculated value is 606.1889, and the measured value is 606.1885. 5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2-[4-(trifluoromethoxy)phenyl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1H NMR (500 MHz, DMSO-d6) δ ppm -0.30 - -0.26 (m, 9 H) 0.46 - 0.55(m, 2 H) 2.94 - 3.01 (m, 2 H) 3.60 (s, 3 H) 5.04 (s, 2 H) 6.90 (s, 1 H) 6.92(d, J=4.12 Hz, 1 H) 7.44 - 7.53 (m, 3 H) 7.61 - 7.68 (m, 4 H) 7.71 - 7.78 (m,1 H) 8.01 (d, J=4.12 Hz, 1 H) 8.17 (dd, J=8.46, 1.14 Hz, 2 H) 8.45 (d, J=5.03Hz, 1H). LCMS: m / z 672 [M+H] + HRMS (ESI) for C 32 H 32 F3N3O6SSi [M+H] + The calculated value is 672.1806, and the measured value is 672.1808. 2-(1-benzothiophene-3-yl)-5-[1-(benzenesulfonyl)-1 H -pyrrolo[2,3- b ]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1 H methyl pyrrole-3-carboxylate (VIII) 1H NMR (500 MHz, DMSO-d6) δ ppm -0.39 - -0.33 (m, 9 H) 0.31 - 0.43(m, 2 H) 2.78 - 2.89 (m, 2 H) 3.49 (s, 3 H) 4.97 (d, J=10.98 Hz, 1 H) 5.21(d, J=10.98 Hz, 1 H) 6.93 (d, J=4.12 Hz, 1 H) 6.99 (s, 1 H) 7.33 - 7.45 (m, 3H) 7.56 (d, J=5.03 Hz, 1 H) 7.62 - 7.69 (m, 2 H) 7.71 - 7.78 (m, 1H) 7.99(s, 1 H) 8.02 (d, J=4.12 Hz, 1 H) 8.04 - 8.12 (m, 1 H) 8.14 - 8.22 (m, 2 H)8.45 (d, J=5.19 Hz, 1 H). LCMS: m / z 644[M+H] + HRMS (ESI) for C 33 H 33 N3O5S2Si [M+H] + The calculated value is 644.1704, and the measured value is 644.17. 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[1-(benzenesulfonyl)-1 H -pyrrolo[2,3- b ]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1 H methyl pyrrole-3-carboxylate (VIII) 1H NMR (500 MHz, DMSO-d6) δ ppm -0.25 (s, 9 H) 0.50 - 0.59 (m, 2 H)2.98 - 3.07 (m, 2 H) 3.61 (s, 3 H) 4.29 (q, J=4.98 Hz, 4 H) 5.04 (s, 2 H)6.86 (s, 1 H) 6.91 (d, J=4.12 Hz, 1 H) 6.92 - 6.96 (m, 2 H) 7.00 (m, J=1.22Hz, 1 H) 7.52 (d, J=5.19 Hz, 1 H) 7.61 - 7.67 (m, 2 H) 7.74 (m, J=7.47 Hz, 1H) 7.99 (d, J=4.12 Hz, 1 H) 8.17 (dd, J=8.39, 1.07 Hz, 2 H) 8.43 (d, J=5.19Hz, 1 H). LCMS: m / z 646 [M+H] + HRMS (ESI) for C 33 H 35 N3O7SSi[M+H] + The calculated value is 646.2038, and the measured value is 646.2045. 2-(4-fluoro-2-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.32 - -0.28 (m, 9 H) 0.40 - 0.50 (m,2 H) 2.08 (s, 3 H) 2.82 - 3.04 (m, 2 H) 3.57 (s, 3 H) 4.79 - 5.05 (m, 2 H)6.84 - 6.92 (m, 2 H) 7.12 (d, J =2.59 Hz, 1 H) 7.21 (dd, J =10.07, 2.59 Hz, 1H) 7.33 (dd, J=8.46, 6.02 Hz, 1 H) 7.47 - 7.52 (m, 1 H) 7.58 - 7.68 (m, 2 H)7.70 - 7.77 (m, 1 H) 8.00 (d, J =3.97 Hz, 1 H) 8.16 (dd, J =8.46, 1.14 Hz, 2 H)8.43 (d, J =5.19 Hz, 1 H). LCMS: m / z 620 [M+H] + HRMS (ESI) for C 32 H 34 FN3O5SSi [M+H] + The calculated value is 620.2045, and the measured value is 620.2034. 2-(2-fluoro-3-methylphenyl)-4-iodo-5-[1-(benzenesulfonyl)-1 H -pyrrolo[2,3- b ]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1 H methyl pyrrole-3-carboxylate (VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.30 (s, 9 H) 0.32 (m, J =9.65, 9.65,6.63 Hz, 2 H) 2.38 (s, 3 H) 2.67 - 2.86 (m, 2 H) 3.53 (s, 3 H) 4.58 - 5.07(m, 2 H) 6.37 - 6.81 (m, 1 H) 7.09 - 7.19 (m, 2 H) 7.39 (d, J =5.03 Hz, 2 H)7.61 - 7.71 (m, 2 H) 7.73 - 7.79 (m, 1 H) 8.02 (d, J =3.97 Hz, 1 H) 8.19 (d, J =7.47 Hz, 2 H) 8.51 (d, J =5.03 Hz, 1 H). LCMS: m / z 746 [M+H] + HRMS (ESI) for C 33 H 33FIN3O5SSi [M+H] + The calculated value is 746.1012, and the measured value is 746.1024. 2-(2-fluoro-3-methylphenyl)-4-bromo-5-[1-(benzenesulfonyl)-1 H -pyrrolo[2,3- b ]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1 H methyl pyrrole-3-carboxylate (VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.34 - -0.27 (m, 9 H) 0.26 - 0.41 (m, 2 H) 2.39 (s, 3 H) 2.80 (m, J =11.13, 11.13, 6.56 Hz, 2 H) 3.55 (s, 3 H) 4.68- 5.18 (m, 2 H) 6.47 - 6.85 (m, 1 H) 7.08 - 7.22 (m, 2 H) 7.30 - 7.48 (m, 2H) 7.59 - 7.70 (m, 2 H) 7.70 - 7.82 (m, 1 H) 8.03 (d, J =3.97 Hz, 1 H) 8.18 -8.22 (m, 2 H) 8.51 (d, J =5.03 Hz, 1 H). LCMS: m / z 698 [M+H] + HRMS (ESI) for C 33 H 33 BrFN3O5SSi [M+H] + The calculated value is 698.1151, and the measured value is 698.1159. Transformation 2 4-Vinyl-2-(2-fluoro-4-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester (VIII) Under an argon atmosphere, methyl 2-(2-fluoro-4-methylphenyl)-4-iodo-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylate (1 equivalent, 50 mg, 0.06 mmol), vinylboric acid (2 equivalents, 23 µl, 0.13 mmol), Na₂CO₃ (3 equivalents, 21.3 mg, 0.2 mmol), degassed 1,4-dioxane (1 ml), and degassed distilled water (0.25 ml) were added to a reactor. After three vacuum / argon cycles, the catalyst tetra(triphenylphosphine)palladium(0) (0.1 equivalents, 7.7 mg, 0.006 mmol) was added. After three vacuum / argon cycles, the reaction mixture was heated at T=100 °C for 2 hours. Add distilled water and extract the product with AcOEt (3 times). Wash the organic layer with distilled water and brine, dry with anhydrous Na2SO4 and evaporate to dryness. Purify the crude product by rapid chromatography (hexane / ethyl acetate 8 / 2) to provide the title compound (white solid, 28 mg, Y=72%).

[0124] 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.32 - -0.28 (m, 9 H) 0.27 - 0.37 (m,2 H) 2.36 - 2.40 (m, 3 H) 2.77 (td, J =10.29, 6.41 Hz, 2 H) 3.50 - 3.54 (m, 3H) 4.64 (d, J =17.54 Hz, 1 H) 4.84 (dd, J =11.44, 1.68 Hz, 1 H) 4.86 - 5.02 (m,2 H) 6.79 (br. s., 2 H) 7.08 - 7.18 (m, 2 H) 7.28 - 7.47 (m, 2 H) 7.60 -7.69 (m, 2 H) 7.74 (t, J =7.40 Hz, 1 H) 7.93 - 8.04 (m, 1 H) 8.11 - 8.22 (m, 2H) 8.45 - 8.53 (m, 1 H). LCMS: m / z 645 [M+H] + HRMS (ESI) for C 34 H 36 FN3O5SSi [M+H] +The calculated value is 646.2202, and the measured value is 646.2194. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(2-fluoro-4-methylphenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-(prop-1-en-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid methyl ester 12(VIII) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.34 - -0.23 (m, 9 H) 0.27 - 0.39 (m,2 H) 1.88 (s, 3 H) 2.38 (s, 3 H) 2.74 - 2.81 (m, 2 H) 3.49 (s, 3 H) 4.44 (d, J =1.37 Hz, 1 H) 4.76 (s, 3 H) 6.39 - 6.76 (m, 1 H) 7.07 - 7.17 (m, 3 H) 7.32(d, J =4.88 Hz, 1 H) 7.62 - 7.68 (m, 2 H) 7.70 - 7.80 (m, 1 H) 7.95 (d, J =4.12Hz, 1 H) 8.17 (d, J =7.47 Hz, 2 H) 8.42 (d, J =5.03 Hz, 1 H). LCMS: m / z 659 [M+H] + HRMS (ESI) for C 35 H 38 FN3O5SSi [M+H] + The calculated value is 660.2358, and the measured value is 660.2358. Step 5 2-(3-Chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) To a solution of methyl 2-(3-chloro-2-fluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylate (1 equivalent, 100 mg, 0.156 mmol) in dioxane (0.5 mL), 0.5 mL of 4 M NaOH solution was added. The reaction mixture was stirred at T = 100 °C for 4 hours. After cooling to room temperature, acetic acid was added to achieve pH = 6. Distilled water was added, and the product was extracted three times with AcOEt. The organic layer was washed with brine, dried over anhydrous Na₂SO₄, and evaporated to dryness. The crude product (white solid, 70 mg, Y = 92%) was used in the next step without further purification.

[0125] 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.24 - -0.18 (m, 9 H) 0.46 - 0.58 (m,2 H) 2.90 - 3.02 (m, 2 H) 5.04 - 5.21 (m, 2 H) 6.53 (dd, J=3.43, 1.91 Hz, 1H) 6.86 (s, 1 H) 7.23 (d, J=5.03 Hz, 1 H) 7.35 (t, J=7.85 Hz, 1 H) 7.53 -7.61 (m, 2 H) 7.67 - 7.73 (m, 1 H) 8.29 (d, J=4.88 Hz, 1 H) 11.86 (br. s., 1H) 12.04 (br. s., 1 H). LCMS: m / z 486 [M+H] + HRMS (ESI) for C 24 H 25 ClFN3O3Si [M+H] + The calculated value is 486.1411, and the measured value is 486.1397. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(4-Chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.23 - -0.18 (m, 9 H) 0.48 - 0.56 (m,2 H) 2.94 - 3.00 (m, 2 H) 5.04 - 5.22 (m, 2 H) 6.52 (dd, J=3.43, 1.91 Hz, 1H) 6.85 (s, 1 H) 7.22 (d, J=4.88 Hz, 1 H) 7.42 (dd, J=8.31, 2.06 Hz, 1 H)7.53 - 7.58 (m, 2 H) 7.61 (t, J=8.08 Hz, 1 H) 8.28 (d, J=5.03 Hz, 1 H) 11.85(br. s., 1 H) 12.08 (br. s., 1 H). LCMS: m / z 486 [M+H] + HRMS (ESI) for C 24 H 25 ClFN3O3Si [M+H] + The calculated value is 486.1411, and the measured value is 486.1417. 2-(2-Chloro-4-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 486 [M+H] + HRMS (ESI) for C 24 H 25 ClFN3O3Si [M+H] + The calculated value is 486.1411, and the measured value is 486.1408. 2-(2,4-Difluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 470 [M+H] + HRMS (ESI) for C 24 H 25 F2N3O3Si[M+H] + The calculated value is 470.1706, and the measured value is 470.1711. 2-[2-chloro-4-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.24 - -0.22 (m, 7 H) 0.42 - 0.52 (m, 2 H) 2.89 - 2.98 (m, 2 H) 4.96 - 5.18 (m, 2 H) 6.49 (dd, J=3.36, 1.83 Hz,1 H) 6.85 (s, 1 H) 7.20 (d, J=4.88 Hz, 1 H) 7.56 - 7.59 (m, 1 H) 7.80 - 7.87 (m, 2 H) 8.03 (s, 1 H) 8.29 (d, J=4.88 Hz, 1 H) 11.87 (br. s., 1 H). LCMS: m / z536 [M+H] + HRMS (ESI) for C 25 H 25 ClF3N3O3Si [M+H] + The calculated value is 536.1379, and the measured value is 536.1384. 2-(2,3-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 470 [M+H] + HRMS (ESI) for C 24 H 25 F2N3O3Si [M+H + The calculated value is 470.1706, and the measured value is 470.1701. 2-(2,3-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 502 [M+H] + HRMS (ESI) for C 24 H 25Cl2N3O3Si [M+H] + The calculated value is 502.1112, and the measured value is 502.1119. 2-[4-methyl-2-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.25 - -0.19 (m, 9 H) 0.49 (ddd, J=9.76, 7.02, 2.29 Hz, 2 H) 2.47 (s, 3 H) 2.86 - 2.99 (m, 2 H) 4.76 (d, J=10.98Hz, 1 H) 5.11 (d, J=10.98 Hz, 1 H) 6.39 (dd, J=3.36, 1.83 Hz, 1 H) 6.79 (s, 1H) 7.16 (d, J=5.03 Hz, 1 H) 7.43 (d, J=7.78 Hz, 1 H) 7.52 - 7.60 (m, 2 H)7.68 (s, 1 H) 8.28 (d, J=4.88 Hz, 1 H) 11.85 (br. s., 1 H). LCMS: m / z 516 [M+H] + HRMS (ESI) for C 26 H 28 F3N3O3Si [M+H] + The calculated value is 516.1925, and the measured value is 516.1931. 2-(2-Chloro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 482 [M+H] + HRMS (ESI) for C 25 H 28 ClN3O3Si [M+H] + The calculated value is 482.1661, and the measured value is 482.1664. 2-(2,3-Difluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 484 [M+H] + HRMS (ESI) for C 25 H 27 F2N3O3Si [M+H + The calculated value is 484.1863, and the measured value is 484.1866. 2-[2-methyl-4-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 516 [M+H] + HRMS (ESI) for C 26 H 28 F3N3O3Si [M+H] + The calculated value is 516.1925, and the measured value is 516.1927. 2-(2-fluoro-3-methoxyphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 482 [M+H] + HRMS (ESI) for C 25 H 28 FN3O4Si [M+H] + The calculated value is 482.1906, and the measured value is 482.1904. 2-(2-Chloro-3-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 486 [M+H] + HRMS (ESI) for C 24 H 25 ClFN3O3Si [M+H] +The calculated value is 486.1411, and the measured value is 486.1409. 2-(2-fluoro-3-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 466 [M+H] + HRMS (ESI) for C 25 H 28 FN3O3Si [M+H] + The calculated value is 466.1957, and the measured value is 466.1951. 2-[2-methyl-3-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 516 [M+H] + HRMS (ESI) for C 26 H 28 F3N3O3Si[M+H] + The calculated value is 516.1925, and the measured value is 516.1919. 2-[4-methoxy-2-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 532 [M+H] + HRMS (ESI) for C 26 H 28 F3N3O4Si [M+H] + The calculated value is 532.1874, and the measured value is 532.1871. 2-[2-chloro-4-(difluoromethoxy)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 534 [M+H] + HRMS (ESI) for C 25 H 26ClF2N3O4Si [M+H] + The calculated value is 534.1422, and the measured value is 534.1423. 2-(3,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 502 [M+H] + HRMS (ESI) for C 24 H 25 Cl2N3O3Si [M+H] + The calculated value is 502.1115, and the measured value is 502.1121. 2-(3,4-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 470 [M+H] + HRMS (ESI) for C 24 H 25 F2N3O3Si [M+H + The calculated value is 470.1706, and the measured value is 470.1715. 2-(3-ethoxy-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.24 - -0.16 (m, 9 H) 0.48 - 0.58 (m,2 H) 1.38 (t, J=6.94 Hz, 1 H) 2.87 - 3.08 (m, 2 H) 4.04 - 4.25 (m, 1 H) 4.95- 5.23 (m, 2 H) 6.52 (dd, J=3.43, 1.91 Hz, 1 H) 6.81 - 6.91 (m, 1 H) 7.02 -7.11 (m, 1 H) 7.18 - 7.32 (m, 3 H) 7.55 - 7.61 (m, 1 H) 8.28 (d, J=4.88 Hz, 1H) 11.85 (br. s., 1 H) 11.95 (br. s., 1 H). LCMS: m / z 496 [M+H] + HRMS (ESI) for C 26 H 30 FN3O4Si [M+H] + The calculated value is 496.2063, and the measured value is 496.2069. 2-(4-Methyl-3-nitrophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.20 - -0.14 (m, 2 H) 0.57 - 0.67 (m,1 H) 2.61 (s, 1 H) 2.99 - 3.11 (m, 1 H) 5.09 (s, 1 H) 6.57 (dd, J=3.36, 1.98Hz, 1 H) 6.88 (s, 1 H) 7.26 (d, J=5.03 Hz, 1 H) 7.55 - 7.65 (m, 1 H) 7.80 (dd, J=7.85, 1.75 Hz, 1 H) 8.18 (d, J=1.68 Hz, 1 H) 8.30 (d, J=4.88 Hz, 1 H)11.60 - 12.24 (m, 1 H). LCMS: m / z 493 [M+H] + HRMS (ESI) for C 25 H 28 N4O5Si [M+H]+ The calculated value is 493.1902, and the measured value is 493.1903. 2-(3-Carboxy-4-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 496 [M+H] + HRMS (ESI) for C 25 H 26 FN3O5Si [M+H + The calculated value is 496.1699, and the measured value is 496.1701. 2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 466 [M+H] + HRMS (ESI) for C 25 H 28 FN3O3Si [M+H] + The calculated value is 466.1957, and the measured value is 466.1959. 2-(dibenzo[b,d]thiophen-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 540 [M+H] + HRMS (ESI) for C 30 H 29 N3O3SSi [M+H] + The calculated value is 540.1772, and the measured value is 540.1775. 2-(4-Methylnaphth-1-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 498 [M+H] + HRMS (ESI) for C 29 H 31N3O3Si [M+H] + The calculated value is 498.2207, and the measured value is 498.2209. 2-(3-Fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 452 [M+H] + HRMS (ESI) for C 24 H 26 FN3O3Si [M+H] + The calculated value is 452.1800, and the measured value is 452.1811. 5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-2-[4-(trifluoromethoxy)phenyl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 518 [M+H] + HRMS (ESI) for C 25 H 26 F3N3O4Si [M+H] + The calculated value is 518.1718, and the measured value is 518.1725. 2-(1-benzothiophene-3-yl)-5-(1 H -pyrrolo[2,3- b ]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1 H 3-pyrrole-3-carboxylic acid (IX) LCMS: m / z 490 [M+H] + For HRMS (ESI) C 26 H 27 N3O3SSi [M+H] + The calculated value is 490.1615, and the measured value is 490.1624. 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-(1 H -pyrrolo[2,3- b ]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1 H 3-pyrrole-3-carboxylic acid (IX) LCMS: m / z 492 [M+H] + HRMS (ESI) for C 26 H 29 N3O5Si [M+H] + The calculated value is 492.1949, and the measured value is 492.1952. 2-(4-fluoro-2-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 466 [M+H] + HRMS (ESI) for C 25 H 28 N3O3Si [M+H] + The calculated value is 466.1957, and the measured value is 466.1959. 2-(2-fluoro-4-methylphenyl)-4-iodo-5-(1 H -pyrrolo[2,3- b ]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1 H 3-pyrrole-3-carboxylic acid (IX) LCMS: m / z 592 [M+H] + HRMS (ESI) for C 25 H 27 FIN3O3Si [M+H] + The calculated value is 592.0923, and the measured value is 592.0929. 2-(2-fluoro-4-methylphenyl)-4-bromo-5-(1 H -pyrrolo[2,3- b ]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1 H 3-pyrrole-3-carboxylic acid (IX) LCMS: m / z 544 [M+H] + HRMS (ESI) C 25 H 27 BrFN3O3Si [M+H] + The calculated value is 544.1062, and the measured value is 544.1067. 4-Vinyl-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 492 [M+H] + HRMS (ESI) for C 27 H 30 FN3O3Si [M+H] + The calculated value is 492.2113, and the measured value is 492.2114. 2-(2-fluoro-4-methylphenyl)-4-(prop-1-en-2-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (IX) LCMS: m / z 506 [M+H] + HRMS (ESI) for C 28 H 32 FN3O3Si [M+H] + The calculated value is 506.2270, and the measured value is 506.2271. Step 6 2-(3-Chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) To a solution of methyl 2-(3-chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (1 equivalent, 70 mg, 0.144 mmol) in DMA (1 mL), DIPEA (6 equivalents, 143 μl, 0.87 mmol), TBTU (2 equivalents, 93 mg, 0.289 mmol), and HOBt NH3 (2 equivalents, 44 mg, 0.289 mmol) were added. The reaction mixture was stirred overnight at room temperature. Distilled water was added, and the product was extracted three times with AcOEt. The organic layer was washed with 0.5 M NaOH and brine, dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by rapid chromatography (DCM / acetone 7 / 3) to provide the title compound (solid, 67 mg, Y = 96%). 1H NMR (500 MHz, DMSO- d 6) δ ppm -0.21 - -0.18 (m, 9 H) 0.52 - 0.58 (m, 2 H) 2.95 - 3.02 (m, 2H) 5.01 - 5.19 (m, 2 H) 6.67 (dd, J=3.43, 1.91 Hz, 1 H) 6.87 (br. s., 1 H)7.08 (s, 1 H) 7.23 (d, J=4.88 Hz, 1 H) 7.30 (t, J=7.93 Hz, 1 H) 7.46 - 7.51(m, 1 H) 7.54 (br. s., 1 H) 7.56 - 7.58 (m, 1 H) 7.62 - 7.68 (m, 1H) 8.28(d, J=5.03 Hz, 1 H) 11.82 (br. s., 1 H). LCMS: m / z 485 [M+H] + HRMS (ESI) for C 24 H 26 ClFN4O2Si [M+H] + The calculated value is 485.1571, and the measured value is 485.1555. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(4-Chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.23 - -0.16 (m, 9 H) 0.50 - 0.59 (m,2 H) 2.94 - 3.04 (m, 2 H) 4.96 - 5.17 (m, 2 H) 6.65 (dd, J=3.43, 1.91 Hz, 1H) 6.86 (br. s., 1 H) 7.06 (s, 1 H) 7.22 (d, J=4.88 Hz, 1 H) 7.38 (dd, J=8.24, 1.83 Hz, 1 H) 7.46 - 7.60 (m, 4 H) 8.27 (d, J=5.03 Hz, 1 H) 11.82 (br.s., 1 H). LCMS: m / z 485 [M+H] + HRMS (ESI) for C 24 H 26 ClFN4O2Si [M+H] + The calculated value is 485.1571, and the measured value is 485.1567. 2-(2-Chloro-4-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) LCMS: m / z 485 [M+H] + HRMS (ESI) for C 24 H 26 ClFN4O2Si [M+H] + The calculated value is 485.1571, and the measured value is 485.1566. 2-(2,4-Difluorophenyl)-5-[1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) LCMS: m / z 469 [M+H] + HRMS (ESI) for C 24 H 26 F2N4O2Si [M+H] + The calculated value is 469.1866, and the measured value is 469.1861. 2-[2-chloro-4-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.24 - -0.20 (m, 9 H) 0.45 - 0.55 (m, 0 H) 2.90 - 2.96 (m, 2 H) 4.87 - 5.20 (m, 2 H) 6.62 (dd, J=3.43, 1.91 Hz,1 H) 6.87 (br. s., 1 H) 7.08 (s, 1 H) 7.20 (d, J=4.88 Hz, 1 H) 7.54 (br. s.,1 H) 7.57 - 7.60 (m, 1 H) 7.71 - 7.76 (m, 1 H) 7.77 - 7.82 (m, 1 H) 7.97 (d,J=0.92 Hz, 1H) 8.28 (d, J=4.88 Hz, 1 H) 11.84 (s, 1 H). LCMS: m / z 535 [M+H] + HRMS (ESI) for C 25 H 26 ClF3N4O2Si [M+H] + The calculated value is 535.1539, and the measured value is 535.1536. 2-(2,3-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) LCMS: m / z 469 [M+H] + HRMS (ESI) for C 24 H 26 F2N4O2Si [M+H] + The calculated value is 469.1866, and the measured value is 469.1862. 2-(2,3-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) LCMS: m / z 501 [M+H] + HRMS (ESI) for C 24 H 26 Cl2N4O2Si[M+H] + The calculated value is 501.1275, and the measured value is 501.1278. 2-[4-methyl-2-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.23 - -0.19 (m, 9 H) 0.46 - 0.57 (m,2 H) 2.46 (s, 3 H) 2.83 - 3.02 (m, 2 H) 4.71 (d, J=10.83 Hz, 1 H) 5.09 (d, J=10.98 Hz, 1 H) 6.52 (dd, J=3.43, 1.91 Hz, 1 H) 6.73 (br. s., 1 H) 7.00 (s, 1H) 7.16 (d, J=4.88 Hz, 1 H) 7.24 (br. s., 1 H) 7.38 (d, J=7.93 Hz, 1 H) 7.53(d, J=7.93 Hz, 1 H) 7.55 - 7.57 (m, 1 H) 7.64 (s, 1 H) 8.26 (d, J=4.88 Hz, 1H) 11.81 (br. s., 1 H). LCMS: m / z 515 [M+H] + HRMS (ESI) for C 26 H 29 F3N4O2Si [M+H] + The calculated value is 515.2085, and the measured value is 515.2093. 2-(2-Chloro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) LCMS: m / z 481 [M+H] + HRMS (ESI) for C 25 H29 ClN4O2Si [M+H] + The calculated value is 481.1821, and the measured value is 481.1825. 2-(2,3-Difluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) LCMS: m / z 483 [M+H] + HRMS (ESI) for C 25 H 28 F2N4O2Si [M+H] + The calculated value is 483.2022, and the measured value is 483.2025. 2-[2-methyl-4-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.25 - -0.19 (m, 9 H) 0.46 - 0.54 (m,2 H) 2.20 (s, 3 H) 2.82 - 2.98 (m, 2 H) 4.89 (d, J=10.83 Hz, 1 H) 5.01 (d, J=10.83 Hz, 1 H) 6.65 (dd, J=3.43, 1.91 Hz, 1 H) 6.83 (br. s., 1 H) 7.08 (s, 1H) 7.21 (d, J=5.03 Hz, 1 H) 7.41 (br. s., 1 H) 7.51 (d, J=7.78 Hz, 1 H) 7.55- 7.57 (m, 1 H) 7.60 (d, J=7.78 Hz, 1 H) 7.67 (s, 1 H) 8.27 (d, J=4.88 Hz, 1H) 11.81 (br. s., 1 H). LCMS: m / z 515 [M+H] + HRMS (ESI) for C 26 H 29 F3N4O2Si [M+H] + The calculated value is 515.2085, and the measured value is 515.2084. 2-(2-fluoro-3-methoxyphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.22 - -0.17 (m, 9 H) 0.54 (t, J=8.39Hz, 2 H) 2.92 - 3.04 (m, 2 H) 3.87 (s, 3 H) 4.99 - 5.05 (m, 1 H) 5.12 - 5.17(m, 1 H) 6.66 (dd, J=3.43, 1.91 Hz, 1 H) 6.81 (br. s., 1 H) 6.98 - 7.03 (m, 1H) 7.04 (s, 1 H) 7.17 - 7.21 (m, 1 H) 7.21 - 7.27 (m, 1 H) 7.38 (br. s., 1 H)7.53-7.57 (m, 1 H) 8.26 (d, J=4.88 Hz, 1 H) 11.80 (s, 1 H). LCMS: m / z 481 [M+H] + HRMS (ESI) for C 25 H 29 FN4O3Si [M+H + The calculated value is 481.2066, and the measured value is 481.2061. 2-(2-Chloro-3-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.24 - -0.17 (m, 9 H) 0.48 - 0.56 (m,2 H) 2.90 - 3.00 (m, 2 H) 4.96 (d, J=11.13 Hz, 1 H) 5.13 (d, J=11.13 Hz, 1 H)6.62 (dd, 7.55 -7.59 (m, 1 H) 8.27 (d, J=5.03 Hz, 1 H) 11.82 (br. s., 1 H). LCMS: m / z 485 [M+H] + HRMS (ESI) for C 24 H 26 ClFN4O2Si [M+H] + The calculated value is 485.1571, and the measured value is 485.1562. 2-(2-fluoro-3-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.21 - -0.17 (m, 9 H) 0.55 (t, J=8.39Hz, 2 H) 2.27 (s, 3 H) 2.95 - 3.04 (m, 2 H) 4.97 - 5.04 (m, 1 H) 5.12 - 5.17(m, 1 H) 6.66 (dd, J=3.43, 1.91 Hz, 1 H) 6.79 (br. s., 1 H) 7.04 (s, 1 H)7.14 - 7.18 (m, 1 H) 7.25 (d, J=5.03 Hz, 1 H) 7.28 - 7.32 (m, 1 H) 7.33 -7.41 (m, 2 H) 7.55 - 7.57 (m, 1 H) 8.26 (d, J=5.03 Hz, 1 H) 11.80 (br. s., 1H). LCMS: m / z 465 [M+H]+ HRMS (ESI) for C 25 H 29 FN4O2Si[M+H] + The calculated value is 465.2117, and the measured value is 465.2108. 2-[2-methyl-3-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) LCMS: m / z 515 [M+H] + HRMS (ESI) for C 26 H 29 F3N4O2Si [M+H] + The calculated value is 515.2085, and the measured value is 515.2081. 2-[4-methoxy-2-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) LCMS: m / z 531 [M+H] + HRMS (ESI) for C 26 H 29 F3N4O3Si [M+H] + The calculated value is 531.2034, and the measured value is 531.2029. 2-[2-chloro-4-(difluoromethoxy)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.22 - -0.19 (m, 9 H) 0.48 - 0.55 (m,2 H) 2.91 - 3.00 (m, 2 H) 4.91 (d, J=10.98 Hz, 1 H) 5.14 (d, J=11.13 Hz, 1 H)6.61 (dd, J=3.36, 1.98 Hz, 1 H) 6.81 (br. s., 1 H) 7.05 (s, 1 H) 7.16 - 7.28 (m, 3 H) 7.37 - 7.45 (m, 3 H) 7.52 - 7.59 (m, 3 H) 8.25 - 8.29 (m, 1 H) 11.82(br. s., 1 H). LCMS: m / z 533 [M+H] + HRMS (ESI) for C 25 H 27 ClF2N4O3Si [M+H] + The calculated value is 533.1582, and the measured value is 533.1585. 2-(3,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.17 -0.13 (m, 8 H) 0.61 - 0.68 (m,1 H) 1.95 (s, 1 H) 2.78 (s, 1 H) 2.94 (s, 1 H) 3.05 - 3.12 (m, 1 H) 5.06 (s,1 H) 6.71 (dd, 7.56 - 7.58 (m,1 H) 7.70 (d, J=8.24 Hz, 1 H) 7.76 (d, J=1.98 Hz, 1 H) 8.27 (d, J=5.03 Hz, 1H) 11.82 (br. s., 1 H). LCMS: m / z 501 [M+H] +HRMS (ESI) for C 24 H 26 Cl2N4O2Si [M+H] + The calculated value is 501.1275, and the measured value is 501.1282. 2-(3,4-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.18 - -0.13 (m, 8 H) 0.58 - 0.66 (m,2 H) 3.03 - 3.11 (m, 2 H) 5.07 (s, 2 H) 6.69 (dd, J=3.43, 1.91 Hz, 1 H) 6.89 (br. s., 1 H) 7.00 (s, 1 H) 7.25 (d, J=4.88 Hz, 1 H) 7.31 - 7.38 (m, 1 H)7.44 (br. s., 1 H) 7.48 - 7.60 (m, 3 H) 8.27 (d, J=4.88 Hz, 1 H) 11.81 (br.s., 1H). LCMS: m / z 469 [M+H] + HRMS (ESI) for C 24 H 26 F2N4O2Si [M+H] + The calculated value is 469.1866, and the measured value is 469.1864. 2-(3-ethoxy-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.22 - -0.18 (m, 8 H) 0.55 (t, J=8.39Hz, 2 H) 1.34 - 1.40 (m, 3 H) 4.12 (quin, J=7.40 Hz, 2 H) 4.98 - 5.19 (m, 2H) 6.66 (dd, J=3.36, 1.98 Hz, 1 H) 6.81 (br. s., 1 H) 6.96 - 7.02 (m, 1 H)7.04 (s, 1 H) 7.13 - 7.29 (m, 3 H) 7.37 (br. s., 1 H) 7.53 - 7.59 (m, 1 H)8.26 (d, J=5.03 Hz, 1H) 11.80 (br. s., 1 H). LCMS: m / z 495 [M+H] + HRMS (ESI) for C 26 H 31 FN4O3Si [M+H + The calculated value is 495.2222, and the measured value is 495.2216. 2-(4-methyl-3-nitrophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.22 - -0.09 (m, 1 H) 0.57 - 0.73 (m,1 H) 2.59 (s, 1 H) 3.06 - 3.14 (m, 1 H) 5.05 (s, 1 H) 6.72 (dd, J=3.36, 1.98Hz, 1 H) 6.93 (br. s., 1 H) 7.05 (s, 1 H) 7.27 (d, J=5.03 Hz, 1 H) 7.52 -7.60 (m, 1 H) 7.74 (dd, J=7.85, 1.75 Hz, 1 H) 8.15 (d, J=1.68 Hz, 1 H) 8.28 (d, J=5.03 Hz, 1H) 11.82 (br. s., 1 H). LCMS: m / z 492 [M+H] + HRMS (ESI) for C 25 H 29N5O4Si [M+H] + The calculated value is 492.2062, and the measured value is 492.2056. 2-(3-Carbamoyl-4-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.13 (s, 9 H) 0.63 - 0.75 (m, 2 H)3.03 - 3.16 (m, 2 H) 5.00 - 5.07 (m, 2 H) 6.67 - 6.77 (m, 1 H) 6.85 - 6.93(m, 1 H) 6.99 - 7.07 (m, 1 H) 7.27 - 7.33 (m, 1 H) 7.33 - 7.40 (m, 1 H) 7.41 - 7.48 (m, 1 H) 7.56 - 7.60 (m, 1 H) 7.61 - 7.66 (m, 1 H) 7.68 - 7.73 (m, 1H) 7.74 - 7.79 (m, 1 H) 7.82 - 7.87 (m, 1 H) 8.26 - 8.31 (m, 1 H) 11.66 -11.98 (m, 1 H). LCMS: m / z 494 [M+H] + HRMS (ESI) for C 25 H 28 FN5O3Si [M+H + The calculated value is 494.2018, and the measured value is 494.2011. 2-(2-fluoro-4-methylphenyl)-N-[2-(morpholin-4-yl)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) To a solution of 2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylic acid (1 equivalent, 90 mg, 19 mmol) in DMA (1.5 mL), DIPEA (3 equivalents, 131 µl, 0.76 mmol), TBTU (2 equivalents, 118.5 mg, 0.38 mmol), and 2-(morpholino-1-yl)ethylamine (1.5 equivalents, 38 µl, 0.28 mmol) were added. The reaction mixture was stirred overnight at room temperature. Distilled water was added, and the product was extracted three times with AcOEt. The organic layer was washed with 0.5 M NaOH and brine, dried over anhydrous Na₂SO₄, and evaporated to dryness. The crude product was purified by rapid chromatography (DCM / MeOH 9 / 1) to provide the title compound (beige solid, 92 mg, Y=84%).

[0126] 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.24 - -0.17 (m, 2 H) 0.54 (t, J=8.39Hz, 1 H) 2.27 - 2.41 (m, 2 H) 2.90 - 3.04 (m, 1 H) 3.19 - 3.28 (m, 1 H) 3.52(t, J=4.50 Hz, 1 H) 4.92 - 5.27 (m, 1 H) 6.64 (dd, J=3.43, 1.91 Hz, 1 H) 6.99 (s, 1 H) 7.07 - 7.15 (m, 1 H) 7.24 (d, J=4.88 Hz, 1 H) 7.38 (t, J=7.85 Hz, 1H) 7.55 - 7.60 (m, 1 H) 7.65 (t, J=5.57 Hz, 1 H) 8.26 (d, J=5.03 Hz, 1 H) 11.81 (s, 1 H). LCMS: m / z 578 [M+H] + HRMS (ESI) for C 31 H 40 FN5O3Si [M+H + The calculated value is 578.2957, and the measured value is 578.2952. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: N-[2-(dimethylamino)ethyl]-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.23 - -0.16 (m, 9 H) 0.54 (t, J=8.39Hz, 1 H) 2.10 (s, 6 H) 2.27 (t, J=6.79 Hz, 2 H) 2.39 (s, 3 H) 2.90 - 3.04 (m,2 H) 3.13 - 3.24 (m, 2 H) 4.94 - 5.23 (m, 2 H) 6.64 (dd, J=3.35, 1.98 Hz, 1H) 7.00 (s, 1 H) 7.04 - 7.15 (m, 2 H) 7.24 (d, J=5.03 Hz, 1 H) 7.36 (t, J=7.85Hz, 1H) 7.57 (t, J=2.97 Hz, 1 H) 7.65 (t, J=5.49 Hz, 1 H) 8.26 (d, J=4.88 Hz, 1 H) 11.81 (br. s., 1 H). LCMS: m / z 536 [M+H] + HRMS (ESI) for C 29 H 38 FN5O2Si [M+H] + The calculated value is 536.2852, and the measured value is 536.2849. 2-(2-fluoro-4-methylphenyl)-N-[2-(pyrrolidine-1-yl)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) LCMS: m / z 562 [M+H] + HRMS (ESI) for C 31 H 40 FN5O2Si [M+H] + The calculated value is 562.3008, and the measured value is 562.3012. [(1R,2S)-2-({[2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-yl]carbonyl}amino)cyclohexyl]tert-butyl carbamate (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.21 (s, 9 H) 0.52 (t, J=8.39 Hz, 2H) 1.16 - 1.67 (m, 15 H) 2.38 (s, 3 H) 2.92 - 3.01 (m, 2 H) 3.52 - 3.66 (m, 1H) 3.89 (br. s., 1 H) 4.92 - 5.26 (m, 2 H) 6.47 - 6.64 (m, 2 H) 6.91 (br. s.,1 H) 7.11 (d, J=10.22 Hz, 3 H) 7.23 (d, J=4.88 Hz, 1 H) 7.35 - 7.48 (m, 1 H)7.56 (t, J=2.97 Hz, 1 H) 8.27 (d, J=4.88 Hz, 1 H) 11.82 (br. s., 1 H). LCMS: m / z 662 [M+H] + HRMS (ESI) for C 36 H 48 FN5O4Si [M+H + The calculated value is 662.3533, and the measured value is 662.3553. 2-(2-fluoro-4-methylphenyl)-N-(furan-2-ylmethyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.25 - -0.16 (m, 9 H) 0.55 (t, J=8.31Hz, 2 H) 2.37 - 2.41 (m, 3 H) 2.95 - 3.05 (m, 2H) 4.27 - 4.39 (m, 2 H) 4.95 -5.26 (m, 2 H) 6.18 (dd, J=3.13, 0.69 Hz, 1 H) 6.37 (dd, J=3.20, 1.83 Hz, 1 H)6.68 (dd, J=3.36, 1.98 Hz, 1 H) 7.04 - 7.14 (m, 3 H) 7.25 (d, J=5.03 Hz, 1 H)7.36 (t, J=7.70 Hz, 1 H) 7.52 - 7.59 (m, 2 H) 8.26 (d, J=4.88 Hz, 1 H) 8.42 (t, J=5.87 Hz, 1 H) 11.81 (br. s., 1 H). LCMS: m / z 545 [M+H] + HRMS (ESI) for C 30 H 33 FN4O3Si [M+H + The calculated value is 545.2379, and the measured value is 545.2383. [2-({[2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-yl]carbonyl}amino)ethyl]tert-butyl methylcarbamate (XI) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.24 - -0.18 (m, 9 H) 0.54 (t, J=8.39Hz, 2 H) 1.27 - 1.41 (m, 9 H) 2.36 - 2.42 (m, 3 H) 2.77 (d, J=10.37 Hz, 2 H)2.89 - 3.05 (m, 2 H) 3.14 - 3.29 (m, 2 H) 4.87 - 5.31 (m, 2 H) 6.64 (d, J=8.69 Hz, 1 H) 6.97 - 7.12 (m, 3 H) 7.24 (d, J=4.88 Hz, 1 H) 7.34 (br. s., 1H) 7.57 (t, J=2.82 Hz, 1 H) 7.99 (br. s., 1 H) 8.26 (d, J=5.03 Hz, 1 H) 11.81 (br. s., 1 H). LCMS: m / z 622 [M+H] + HRMS (ESI) for C 33 H 44 FN5O4Si [M+H + The calculated value is 622.322, and the measured value is 622.3234. N-(2-Fluoroethyl)-2-(2-Fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.21 - -0.17 (m, 9 H) 0.55 (t, J=8.39Hz, 2 H) 2.36 - 2.41 (m, 3 H) 2.95 - 3.05 (m, 2 H) 3.38 - 3.47 (m, 1 H) 4.39(t, J=5.19 Hz, 1 H) 4.48 (t, J=5.19 Hz, 1 H) 4.89 - 5.28 (m, 2 H) 6.68 (dd, J=3.43, 1.91 Hz, 1 H) 7.05 - 7.13 (m, 3 H) 7.26 (d, J=4.88 Hz, 1 H) 7.36 (t, J=7.63 Hz, 1H) 7.52 - 7.62 (m, 1 H) 8.16 (t, J=5.57 Hz, 1 H) 8.26 (d, J=5.03Hz, 1 H) 11.81 (br. s., 1 H). LCMS: m / z 511 [M+H] + HRMS (ESI) for C 27 H 32 F2N4O2Si [M+H] + The calculated value is 511.2336, and the measured value is 511.2336. 2-(2-fluoro-4-methylphenyl)-N-(1-methylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.28 - -0.14 (m, 9 H) 0.54 (t, J=8.39Hz, 2 H) 1.53 (d, J=9.15 Hz, 2 H) 1.74 (br. s., 2 H) 2.15 - 2.35 (m, 2 H)2.38 (s, 3H) 2.74 - 3.05 (m, 4 H) 3.65 (br. s., 1 H) 4.91 - 5.29 (m, 2 H)6.65 (dd, J=3.36, 1.98 Hz, 1 H) 7.05 (s, 1 H) 7.07 - 7.12 (m, 2 H) 7.24 (d, J=4.88 Hz, 1 H) 7.37 (t, J=7.78 Hz, 1 H) 7.53 - 7.59 (m, 1 H) 7.63 (br. s., 1H) 8.26 (d, J=4.88 Hz, 1 H) 11.81 (br. s., 1 H). LCMS: m / z 562 [M+H] + HRMS (ESI) for C 31 H 40 FN5O2Si [M+H] + The calculated value is 562.3008, and the measured value is 562.2991. 2-(dibenzo[b,d]thiophen-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) LCMS: m / z 539 [M+H] + HRMS (ESI) for C 30 H 30 N4O2SSi [M+H] + The calculated value is 539.1932, and the measured value is 539.1938. 2-(4-methylnaphthyl-1-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d6) δ ppm -0.32 - -0.26 (m, 9 H) 0.26 - 0.36 (m,2 H) 2.68 - 2.83 (m, 5 H) 4.73 - 5.08 (m, 2 H) 6.65 - 6.77 (m, 2 H) 6.86 -6.99 (m, 1 H) 7.12 (s, 1 H) 7.28 (d, J=5.03 Hz, 1 H) 7.43 - 7.54 (m, 4 H)7.55 - 7.61 (m, 2 H) 8.09 (d, J=8.39 Hz, 1 H) 8.26 (d, J=5.03 Hz, 1 H) 11.81 (br. s., 1 H). LCMS: m / z 497 [M+H] + HRMS (ESI) for C 29 H 32 N4O2Si [M+H] + The calculated value is 497.2368, and the measured value is 497.2369. 2-(3-Fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO-d6) δ ppm -0.20 - -0.12 (m, 9 H) 0.57 - 0.67(m, 2 H) 3.01 - 3.10 (m, 2 H) 5.06 (s, 2 H) 6.70 (dd, J=3.43, 1.91 Hz, 1 H)6.88 (br. s., 1 H) 6.99 (s, 1 H) 7.22 - 7.30 (m, 2 H) 7.30 - 7.36 (m, 2 H)7.39 (br. s., 1 H) 7.44 - 7.52 (m, 1 H) 7.52 - 7.60 (m, 1 H) 8.27 (d, J=4.88Hz, 1 H) 11.80 (br. s., 1 H). LCMS: m / z 451 [M+H] + HRMS (ESI) for C 24 H 27 FN4O2Si [M+H] + The calculated value is 451.196, and the measured value is 451.1948. 5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-2-[4-(trifluoromethoxy)phenyl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO-d6) δ ppm -0.22 - -0.14 (m, 9 H) 0.52 - 0.67(m, 2 H) 2.92 - 3.11 (m, 2 H) 5.05 (s, 2 H) 6.70 (dd, J=3.36, 1.98 Hz, 1 H)6.82 - 6.91 (m, 1 H) 7.01 (s, 1 H) 7.26 (d, J=5.03 Hz, 1 H) 7.43 (m, 3 H)7.53 - 7.58 (m, 1 H) 7.59 - 7.66 (m, 2 H) 8.27 (d, J=4.88 Hz, 1 H) 11.80 (br.s., 1 H). LCMS: m / z 517 [M+H] + HRMS (ESI) for C 25 H 27 F3N4O3Si [M+H] + The calculated value is 517.1878, and the measured value is 517.1857. 2-(1-Benzothiophene-3-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.28 - -0.25 (m, 9 H) 0.39 - 0.49 (m, 2 H) 2.88 (dd, J =9.00, 7.78 Hz, 2 H) 4.97 (d, J =10.83 Hz, 1 H) 5.22 (d, J =10.83 Hz, 1 H) 6.70 (dd, J=3.43, 1.91 Hz, 1 H) 6.78 - 6.86 (m, 1 H) 7.10 (s,1 H) 7.24 (br. s., 1 H) 7.29 (d, J =5.03 Hz, 1 H) 7.34 - 7.42 (m, 2 H) 7.43 -7.47 (m, 1 H) 7.57 (t, J =1.00 Hz, 1 H) 7.93 (s, 1 H) 8.04 (m, J =7.09, 1.14Hz, 1 H) 8.27 (d, J =5.03 Hz, 1 H) 11.81 (br. s., 1 H). LCMS: m / z 489 [M+H] + HRMS (ESI) for C 26 H 28 N4O2SSi [M+H] + The calculated value is 489.1775, and the measured value is 489.1761. 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.17 - -0.12 (m, 9 H) 0.61 - 0.70 (m,2 H) 3.03 - 3.13 (m, 2 H) 4.21 - 4.34 (m, 4 H) 5.04 (s, 2 H) 6.68 (dd, J =3.43, 1.91 Hz, 1 H) 6.84 (br. s., 1 H) 6.89 - 6.98 (m, 3 H) 7.01 (d, J =1.98Hz, 1 H) 7.06 (br. s., 1 H) 7.27 (d, J =5.03 Hz, 1 H) 7.54 (t, J =1.00 Hz, 1 H)8.25 (d, J =5.03 Hz, 1 H) 11.77 (br. s., 1 H). LCMS: m / z 491 [M+H]+ HRMS (ESI) for C 26 H 30 N4O4Si [M+H] + The calculated value is 491.2109, and the measured value is 491.2094. 2-(4-fluoro-2-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.22 - -0.19 (m, 9 H) 0.54 (t, J =8.39Hz, 2 H) 2.12 (s, 3 H) 2.86 - 3.01 (m, 2 H) 4.88 (d, J =10.83 Hz, 1 H) 5.01(d, J =10.68 Hz, 1 H) 6.63 (dd, J =3.36, 1.98 Hz, 1 H) 6.79 (br. s., 1 H) 7.03(s, 1 H) 7.09 (td, J =8.58, 2.82 Hz, 1 H) 7.12 - 7.19 (m, 2 H) 7.22 (d, J =5.03Hz, 1 H) 7.32 (dd, J =8.39, 6.10 Hz, 1 H) 7.53 - 7.57 (m, 1 H) 8.25 (d, J =5.03Hz, 1H) 11.79 (br. s., 1H). LCMS: m / z 465 [M+H] + HRMS (ESI) for C 25 H 29 FN4O2Si [M+H] + The calculated value is 465.2117, and the measured value is 465.2126. 2-(2-Fluoro-4-methylphenyl)-4-iodo-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.27 - -0.23 (m, 9 H) 0.36 (t, J =7.70Hz, 2 H) 2.36 - 2.40 (m, 3 H) 2.74 - 2.89 (m, 2 H) 4.93 (br. s., 1 H) 6.04 -6.40 (m, 1 H) 6.99 (d, J =4.88 Hz, 2 H) 7.07 - 7.21 (m, 3 H) 7.43 (br. s., 1H) 7.54 - 7.61 (m, 1 H) 8.28 - 8.38 (m, 1 H) 11.87 (br. s., 1 H). LCMS: m / z 591[M+H] + HRMS (ESI) for C 25 H 28 FIN4O2Si [M+H] + The calculated value is 591.1083, and the measured value is 591.1073. 2-(2-fluoro-4-methylphenyl)-4-bromo-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.35 - -0.19 (m, 9 H) 0.37 (t, J =7.78Hz, 2 H) 2.38 (s, 3 H) 2.76 - 2.92 (m, 2 H) 4.90 - 5.23 (m, 2 H) 6.32 (br.s., 1 H) 6.84 - 7.25 (m, 4 H) 7.43 (br. s., 1 H) 7.59 (t, J =2.97 Hz, 1 H)8.33 (d, J =4.88 Hz, 1 H) 11.88 (br. s., 1 H). LCMS: m / z 543 [M+H] + HRMS (ESI) for C 25 H 28 BrFN4O2Si [M+H]+ The calculated value is 543.1222, and the measured value is 543.1221. 4-Vinyl-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XIa) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.32 - -0.18 (m, 9 H) 0.38 (br. s., 2H) 2.33 - 2.42 (m, 3 H) 2.72 - 2.91 (m, 2 H) 4.90 (d, J =12.81 Hz, 3 H) 5.28(d, J =17.69 Hz, 1 H) 6.22 (br. s., 1 H) 6.44 (dd, J =17.77, 11.67 Hz, 1 H)7.01 - 7.29 (m, 5 H) 7.44 (t, J =7.85 Hz, 1 H) 7.56 (br. s., 1 H) 8.26 - 8.39 (m, 1 H) 11.84 (br. s., 1 H). LCMS: m / z 491 [M+H] + HRMS (ESI) for C 27 H 31 FN4O2Si [M+H] + The calculated value is 491.2273, and the measured value is 491.2267. 2-(2-fluoro-4-methylphenyl)-4-(prop-1-en-2-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XIa) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.23 (s, 9 H) 0.38 (t, J =8.31 ​​Hz, 2H) 1.76 (s, 3 H) 2.36 - 2.39 (m, 3 H) 2.71 - 2.89 (m, 2 H) 4.75 (d,J =1.68Hz, 1 H) 4.86 (br. s., 3 H) 6.22 (br. s., 1 H) 6.75 (br. s., 1 H) 6.93 - 7.06 (m, 2 H) 7.07 - 7.17 (m, 2 H) 7.37 - 7.66 (m, 2 H) 8.25 (d, J =4.88 Hz, 1 H)11.77 (br. s., 1 H). LCMS: m / z 505 [M+H] + HRMS (ESI) for C 28 H 33 FN4O2Si [M+H] + The calculated value is 505.243, and the measured value is 505.2415. Transformation 3 2-(2-fluoro-4-methylphenyl)-4-(propyl-2-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) At 60°C, a solution of 2-(2-fluoro-4-methylphenyl)-4-(prop-1-en-2-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (1 equivalent, 50 mg, 0.1 mmol) in DCM / MeOH 1 / 1 (2 ml) was pumped into an H-Cube. ® In the apparatus, the flow rate was 1 ml / min and the pressure was 60 bar. The catalyst used was a CatCart catalyst. ® The Pd / C content was 10%. The product was separated from a 25 ml product solution and analyzed by HPLC. The solvent was evaporated, and the crude product was purified by rapid chromatography (DCM / MeOH 85 / 15) to provide the title compound (white solid, 48 mg, Y = 97%).

[0127] 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.23 (s, 9 H) 0.29 - 0.40 (m, 2 H)1.12 - 1.22 (m, 6 H) 2.36 (s, 3 H) 2.75 (br. s., 2 H) 2.84 (quin, J=7.02 Hz,1 H) 4.64 - 5.02 (m, 2 H) 6.19 (br. s., 1 H) 6.54 - 6.86 (m, 1 H) 6.92 (br.s., 1 H) 6.99 (d, J =4.88 Hz, 1 H) 7.07 - 7.16 (m, 2 H) 7.39 (br. s., 1 H)7.51 - 7.57 (m, 1 H) 8.29 (d, J =4.73 Hz, 1 H) 11.81 (br. s., 1 H). LCMS: m / z507 [M+H] + HRMS (ESI) for C 28 H 35 FN4O2Si [M+H] + The calculated value is 507.2586, and the measured value is 507.2566. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 4-Ethyl-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XI) 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.24 (s, 9 H) 0.37 (br. s., 2 H) 0.92 (t, J =7.40 Hz, 3 H) 2.37 (s, 4 H) 2.70 - 2.91 (m, 2 H) 4.87 (br. s., 2 H)6.25 (br. s., 1 H) 6.64 (br. s., 1 H) 6.92 (br. s., 1 H) 7.03 (d, J =4.12 Hz,1 H) 7.08 - 7.19 (m, 2 H) 7.43 (t, J =7.85 Hz, 1 H) 7.53 (t, J =2.90 Hz, 1 H)8.29 (d, J =4.88 Hz, 1 H) 11.80 (br. s., 1 H). LCMS: m / z 493 [M+H] +HRMS (ESI) for C 27 H 33 FN4O2Si [M+H] + The calculated value is 493.243, and the measured value is 493.2415. Step 7 2-(3-Chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=3-chloro-2-fluorophenyl, R3=R4=R5=H] Compound 1 TFA (75 equivalents, 9.3 mmol, 711 µl) was added to a solution of 2-(3-chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (1 equivalent, 60 mg, 0.12 mmol) in DCM (2.6 mL). The reaction mixture was stirred at room temperature for 5 hours. The solvent was removed under reduced pressure, and the crude product was treated three times with toluene. In the same reactor, 2-(3-chloro-2-fluorophenyl)-1-(hydroxymethyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (1 equivalent, 60 mg, 0.12 mmol) in DCM (2.6 mL) was added. H 3-pyrrole-3-carboxamide was dissolved in 95% EtOH (0.6 ml), and 30%-32% ammonium hydroxide solution (0.3 ml) was added. The reaction mixture was stirred at room temperature for 2 hours, and precipitate formation was observed. The solid was filtered and washed three times with distilled water (to remove CF3COO). - NH4 + The sample was washed three times with DCM / Et2O 1 / 1 to obtain the title compound (pale yellow solid, 36 mg, Y = 82%).

[0128] 1 H NMR (500 MHz, DMSO- d6) δ ppm 6.84 (br. s., 1 H) 7.01 (dd, J=3.5,2.0 Hz, 1 H) 7.28 (t, J=7.9 Hz, 1 H) 7.39 (d, J=5.2 Hz, 1 H) 7.43 (d, J=2.7Hz, 1 H) 7.50 - 7.53 (m, 1 H) 7.55 - 7.57 (m, 1 H) 7.58 - 7.62 (m, 1 H) 7.63 (br. s., 1 H) 8.20 (d, J=5.0 Hz, 1 H) 11.71 (br. s., 1 H) 12.03 (d, J=1.8 Hz, 1 H). LCMS: m / z 355 [M+H] + HRMS (ESI) for C 18 H 12 ClFN4O [M+H] + The calculated value is 355.0757, and the measured value is 355.0758. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(4-Chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=4-chloro-2-fluorophenyl, R3=R4=R5=H] Compound 2 1 H NMR (500 MHz, DMSO- d 6) δ ppm 6.83 (br. s., 1 H) 7.00 (dd, J=3.5,1.8 Hz, 1 H) 7.35 (dd, J=8.2, 2.0 Hz, 1 H) 7.38 (d, J=5.2 Hz, 1 H) 7.42 (d, J=2.6 Hz, 1 H) 7.46 - 7.51 (m, 1 H) 7.52 - 7.56 (m, 1 H) 7.57 - 7.59 (m, 1 H)7.60 (br. s., 1 H) 8.20 (d, J=5.0 Hz, 1 H) 11.71 (br. s., 1 H) 11.98 (d, J=2.0 Hz, 1H). LCMS: m / z 355 [M+H] + HRMS (ESI) for C 18 H 12ClFN4O [M+H] + The calculated value is 355.0757, and the measured value is 355.0757. 2-(2-Chloro-4-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-chloro-4-fluorophenyl, R3=R4=R5=H] Compound 3 1 H NMR (500 MHz, DMSO- d 6) δ ppm 6.76 (br. s., 1 H) 7.02 (dd, J=3.4,1.9 Hz, 1 H) 7.28 (td, J=8.5, 2.7 Hz, 1 H) 7.37 (d, J=5.2 Hz, 1 H) 7.44 (d, J=2.7 Hz, 1 H) 7.49 - 7.57 (m, 4 H) 8.17 (d, J=5.0 Hz, 1 H) 11.69 (br. s., 1H) 11.96 (d, J=2.1 Hz, 1 H). LCMS: m / z 355 [M+H] + HRMS (ESI) for C 18 H 12 ClFN4O [M+H] + The calculated value is 355.0757, and the measured value is 355.0756. 2-(2,4-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2,4-difluorophenyl, R3=R4=R5=H] Compound 4 1 H NMR (500 MHz, DMSO- d6) δ ppm 6.80 (br. s., 1 H) 7.01 (dd, J=3.6,1.9 Hz, 1 H) 7.15 (td, J=8.5, 2.3 Hz, 1 H) 7.30 (td, J=9.8, 2.6 Hz, 1 H) 7.39(d, J=5.2 Hz, 1 H) 7.42 (d, J=2.7 Hz, 1 H) 7.53 - 7.56 (m, 1 H) 7.56 - 7.62 (m, 2 H) 8.19 (d, J=5.0 Hz, 1 H) 11.70 (br. s., 1 H) 11.96 (d, J=1.8 Hz, 1H). LCMS: m / z 339 [M+H] + HRMS (ESI) for C 18 H 12 F2N4O [M+H] + The calculated value is 339.1052, and the measured value is 339.1048. 2-[2-chloro-4-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-chloro-4-(trifluoromethyl)phenyl, R3=R4=R5=H] Compound 5 1 H NMR (500 MHz, DMSO- d 6) δ ppm 6.80 (br. s., 1 H) 7.03 (dd, J=3.4,1.8 Hz, 1 H) 7.36 (d, J=5.1 Hz, 1 H) 7.48 (d, J=2.4 Hz, 1 H) 7.54 - 7.57 (m,1 H) 7.61 (br. s., 1 H) 7.70 - 7.79 (m, 2 H) 7.94 (s, 1 H) 8.19 (d, J=5.0 Hz,1 H) 11.69 (br. s., 1 H) 12.04 (br. s., 1 H). LCMS: m / z 405 [M+H] + HRMS (ESI) for C 19 H 12 ClF3N4O [M+H] + The calculated value is 405.0725, and the measured value is 405.0724. 2-(2,3-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2,3-difluorophenyl, R3=R4=R5=H] Compound 6 1 H NMR (500 MHz, DMSO- d 6) δ ppm 6.81 (br. s., 1 H) 7.01 (dd, J=3.5,1.8 Hz, 1 H) 7.21 - 7.30 (m, 1 H) 7.33 - 7.49 (m, 4 H) 7.55 (t, J=3.1 Hz, 1H) 7.60 (br. s., 1 H) 8.20 (d, J=5.0 Hz, 1 H) 11.69 (br. s., 1 H) 12.01 (br.s., 1 H). LCMS: m / z 339 [M+H] + HRMS (ESI) for C 18 H 12 F2N4O [M+H] + The calculated value is 339.1052, and the measured value is 339.1046. 2-(2,3-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2,3-dichlorophenyl, R3=R4=R5=H] Compound 7 1 H NMR (500 MHz, DMSO- d 6) δ ppm 6.78 (br. s., 1 H) 7.02 (dd, J=3.5,2.0 Hz, 1 H) 7.36 (d, J=5.2 Hz, 1 H) 7.39 - 7.43 (m, 1 H) 7.44 - 7.47 (m, 2H) 7.54 - 7.56 (m, 1 H) 7.57 (br. s., 1 H) 7.68 (dd, J=7.9, 1.8 Hz, 1 H) 8.18 (d, J=5.2 Hz, 1 H) 11.70 (br. s., 1 H) 12.01 (d, J=1.8 Hz, 1 H). LCMS: m / z 371[M+H] +HRMS (ESI) for C 18 H 12 Cl2N4O [M+H] + The calculated value is 371.0461, and the measured value is 371.0463. 2-[4-methyl-2-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=4-methyl-2-(trifluoromethyl)phenyl, R3=R4=R5=H] Compound 8 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.46 (s, 3 H) 6.66 (br. s., 1 H) 7.01 (dd, J=3.51, 1.83 Hz, 1 H) 7.33 (d, J=5.19 Hz, 1 H) 7.39 (d, J=7.78 Hz, 2 H)7.42 (d, J=2.75 Hz, 1 H) 7.48 - 7.51 (m, 1 H) 7.53 - 7.54 (m, 1 H) 7.62 (s, 1H) 8.15 (d, J=5.19 Hz, 1 H) 11.67 (br. s., 1 H) 11.91 (d, J=1.98 Hz, 1 H). LCMS: m / z 385 [M+H] + HRMS (ESI) for C 20 H 15 F3N4O [M+H] + The calculated value is 385.1271, and the measured value is 385.1270. 2-(2-Chloro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-chloro-4-methylphenyl, R3=R4=R5=H] Compound 9 1H NMR (500 MHz, DMSO-d6) δ ppm 2.35 - 2.40 (m, 3 H) 6.68 - 6.78 (m,1 H) 7.01 (dd, J=3.5, 1.8 Hz, 1 H) 7.20 (dd, J=7.9, 0.8 Hz, 1 H) 7.33 - 7.38(m, 3 H) 7.39 - 7.43 (m, 2 H) 7.52 - 7.55 (m, 1 H) 8.16 (d, J=5.2 Hz, 1 H) 11.67 (br. s., 1 H) 11.88 (d, J=1.8 Hz, 1 H). LCMS: m / z 351 [M+H] + HRMS (ESI) for C 19 H 15 ClN4O [M+H] + The calculated value is 351.1007, and the measured value is 351.1008. 2-(2,3-Difluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2,3-difluoro-4-methylphenyl, R3=R4=R5=H] Compound 10 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.32 - 2.36 (m, 3 H) 6.82 (br. s., 1H) 7.00 (dd, J=3.4, 1.9 Hz, 1 H) 7.12 - 7.16 (m, 1 H) 7.22 - 7.26 (m, 1 H)7.39 (d, J=5.2 Hz, 1 H) 7.41 (d, J=2.6 Hz, 1 H) 7.53 - 7.56 (m, 1 H) 7.59(br. s., 1 H) 8.20 (d, J=5.2 Hz, 1 H) 11.70 (br. s., 1 H) 11.97 (br. s., 1H). LCMS: m / z 353 [m+H] + HRMS (ESI) for C 19 H 14 F2N4O [M+H] + The calculated value is 353.1209, and the measured value is 353.121. 2-[2-methyl-4-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-methyl-4-(trifluoromethyl)phenyl, R3=R4=R5=H] Compound 11 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.28 (s, 3 H) 6.80 (br. s., 1 H) 7.03 (dd, J=3.5, 2.0 Hz, 1 H) 7.38 (d, J=5.2 Hz, 1 H) 7.47 - 7.49 (m, 1 H) 7.50 -7.53 (m, 1 H) 7.53 - 7.60 (m, 3 H) 7.66 (s, 1 H) 8.17 (d, J=5.2 Hz, 1 H) 11.68 (br. s., 1 H) 11.90 (d, J=2.1 Hz, 1 H). LCMS: m / z 385 [M+H] + HRMS (ESI) for C 20 H 15 F3N4O [M+H] + The calculated value is 385.1271, and the measured value is 385.127. 2-(2-fluoro-3-methoxyphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-3-methoxyphenyl, R3=R4=R5=H] Compound 12 1 H NMR (500 MHz, DMSO-d6) δ ppm 3.87 (s, 3 H) 6.77 (br. s., 1 H) 7.00 (dd, J=3.5, 1.8 Hz, 1 H) 7.03 - 7.08 (m, 1 H) 7.13 - 7.21 (m, 2 H) 7.37 -7.41 (m, 2 H) 7.51 (br. s., 1 H) 7.53 - 7.55 (m, 1 H) 8.18 (d, J=5.0 Hz, 1 H) 11.68 (br. s., 1 H) 11.93 (d, J=2.0 Hz, 1 H). LCMS: m / z 351 [M+H]+ HRMS (ESI) for C 19 H 15 FN4O2[M+H] + The calculated value is 351.1252, and the measured value is 351.1252. 2-(2-Chloro-3-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-chloro-3-fluorophenyl, R3=R4=R5=H] Compound 13 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.79 (br. s., 1 H) 7.03 (dd, J=3.4,1.9 Hz, 1 H) 7.32 - 7.36 (m, 1 H) 7.38 (d, J=5.2 Hz, 1 H) 7.41 - 7.48 (m, 3H) 7.53 - 7.62 (m, 2 H) 8.18 (d, J=5.2 Hz, 1 H) 11.72 (br. s., 1 H) 12.02 (br. s., 1 H). LCMS: m / z 355 [M+H] + HRMS (ESI) for C 18 H 12 ClFN4O [M+H] + The calculated value is 355.0757, and the measured value is 355.0755. 2-(2-fluoro-3-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-3-methylphenyl, R3=R4=R5=H] Compound 14 1H NMR (500 MHz, DMSO-d6) δ ppm 2.28 (d, J=0.9 Hz, 3 H) 6.76 (br. s.,1 H) 7.00 (dd, J=3.4, 1.9 Hz, 1 H) 7.11 - 7.16 (m, 1 H) 7.32 (dt, J=19.9, 7.2Hz, 2 H) 7.38 - 7.42 (m, 2 H) 7.50 (br. s., 0 H) 7.53 - 7.56 (m, 1 H) 8.18 (d, J=5.0 Hz, 1 H) 11.68 (br. s., 1 H) 11.90 (br. s., 1 H). LCMS: m / z 335 [M+H] + HRMS (ESI) for C 19 H 15 FN4O [M+H] + The calculated value is 335.1303, and the measured value is 335.1299. 2-[2-methyl-3-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-methyl-3-(trifluoromethyl)phenyl, R3=R4=R5=H] Compound 15 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.27 (s, 3 H) 6.90 (br. s., 1 H) 7.33 (br. s., 1 H) 7.44 - 7.50 (m, 1 H) 7.61 (d, J=7.47 Hz, 1 H) 7.69 (d, J=5.80Hz, 2 H) 7.74 - 7.86 (m, 3 H) 8.37 (d, J=6.10 Hz, 1 H) 12.34 (br. s., 1 H)12.56 (br. s., 1 H). LCMS: m / z 385 [M+H] + HRMS (ESI) for C 20 H 15 F3N4O [M+H] + The calculated value is 385.1271, and the measured value is 385.1276. 2-[4-methoxy-2-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=4-methoxy-2-(trifluoromethyl)phenyl, R3=R4=R5=H] Compound 16 1 H NMR (500 MHz, DMSO-d6) δ ppm 3.89 (s, 3 H) 6.65 (br. s., 1 H) 7.01 (dd, J=3.43, 1.91 Hz, 1 H) 7.24 - 7.30 (m, 2 H) 7.33 (d, J=5.03 Hz, 2 H) 7.40- 7.45 (m, 2 H) 7.52 - 7.55 (m, 1 H) 8.15 (d, J=5.03 Hz, 1 H) 11.66 (br. s.,1 H) 11.89 (d, J=2.29 Hz, 1 H). LCMS: m / z 401 [M+H] + HRMS (ESI) for C 20 H 15 F3N4O2[M+H] + The calculated value is 401.122, and the measured value is 401.1208. 2-[2-chloro-4-(difluoromethoxy)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-chloro-4-(difluoromethoxy)phenyl, R3=R4=R5=H] Compound 17 1 H NMR (500 MHz, DMSO-d6) δ ppm 3.89 (s, 3 H) 6.65 (br. s., 1 H) 7.01 (dd, J=3.43, 1.91 Hz, 1 H) 7.24 - 7.30 (m, 2 H) 7.33 (d, J=5.03 Hz, 2 H) 7.40- 7.45 (m, 2 H) 7.52 - 7.55 (m, 3 H) 8.15 (d, J=5.03 Hz, 1 H) 11.66 (br. s.,1 H) 11.89 (d, J=2.29 Hz, 1 H). LCMS: m / z 403 [M+H]+ HRMS (ESI) for C 19 H 13 ClF2N4O2[M+H] + The calculated value is 403.07679, and the measured value is 403.0769. 2-(3,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=3,4-dichlorophenyl, R3=R4=R5=H] Compound 18 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.92 - 7.04 (m, 2 H) 7.36 (d, J=2.59Hz, 1 H) 7.47 (d, J=5.03 Hz, 1 H) 7.52 - 7.57 (m, 1 H) 7.64 - 7.75 (m, 3 H)8.00 (d, J=1.98 Hz, 1 H) 8.22 (d, J=5.03 Hz, 1 H) 11.71 (br. s., 1 H) 11.88 (d, J=1.83 Hz, 1 H). LCMS: m / z 371 [M+H] + HRMS (ESI) for C 18 H 12 Cl2N4O [M+H] + The calculated value is 371.0461, and the measured value is 371.0458. 2-(3,4-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=3,4-difluorophenyl, R3=R4=R5=H] Compound 19 1H NMR (500 MHz, DMSO-d6) δ ppm 6.88 - 7.03 (m, 2 H) 7.35 (d, J=2.59Hz, 1 H) 7.43 - 7.61 (m, 4 H) 7.66 (br. s., 1 H) 7.83 (ddd, J=12.32, 8.12,1.98 Hz, 1 H) 8.21 (d, J=5.03 Hz, 1 H) 11.46 - 11.96 (m, 2 H). LCMS: m / z 339 [M+H] + HRMS (ESI) for C 18 H 12 F2N4O [M+H] + The calculated value is 339.1052, and the measured value is 339.1049. 2-(3-ethoxy-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=3-ethoxy-2-fluorophenyl, R3=R4=R5=H] Compound 20 1 H NMR (500 MHz, DMSO-d6) δ ppm 1.38 (t, J=7.02 Hz, 3 H) 4.13 (q, J=7.02 Hz, 2 H) 6.77 (br. s., 1 H) 7.00 (dd, J=3.51, 1.98 Hz, 1 H) 7.03 - 7.09(m, 1 H) 7.11 - 7.20 (m, 2 H) 7.36 - 7.44 (m, 2 H) 7.46 - 7.58 (m, 2 H) 8.18(d, J=5.03 Hz, 1 H) 11.36 - 12.12 (m, 2 H). LCMS: m / z 365 [M+H] + HRMS (ESI) for C 20 H 17 FN4O2[M+H] + The calculated value is 365.1409, and the measured value is 365.141. 2-(4-Methyl-3-nitrophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=4-methyl-3-nitrophenyl, R3=R4=R5=H] Compound 21 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.57 (s, 3 H) 6.96 (br. s., 1 H) 7.00 (br. s., 1 H) 7.39 (d, J=2.59 Hz, 1 H) 7.47 (d, J=5.19 Hz, 1 H) 7.50 - 7.57(m, 2 H) 7.72 (br. s., 1 H) 7.97 (dd, J=7.85, 1.75 Hz, 1 H) 8.22 (d, J=5.19Hz, 1 H) 8.37 (d, J=1.83 Hz, 1 H) 11.43 - 12.13 (m, 2 H). LCMS: m / z 362 [M+H] + HRMS (ESI) for C 19 H 15 N5O3[M+H] + The calculated value is 362.1248, and the measured value is 362.1241. 2-(3-Carbamoyl-4-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=3-carbamoyl-4-fluorophenyl, R3=R4=R5=H] Compound 22 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.87 (br. s., 1 H) 7.01 (dd, J=3.36,1.83 Hz, 1 H) 7.31 (dd, J=10.37, 8.69 Hz, 1 H) 7.37 (d, J=2.44 Hz, 1 H) 7.41- 7.51 (m, 1 H) 7.52 - 7.57 (m, 1 H) 7.59 - 7.78 (m, 1 H) 7.85 (ddd, J=8.46,4.88, 2.36 Hz, 1 H) 7.96 (dd, J=7.02, 2.29 Hz, 1 H) 8.21 (d, J=5.19 Hz, 1 H)11.71 (br. s., 1 H) 11.84 (br. s., 1 H). LCMS: m / z 364 [M+H] + HRMS (ESI) for C19 H 14 FN5O2[M+H] + The calculated value is 364.1205, and the measured value is 364.1204. 2-(2-fluoro-4-methylphenyl)-N-[2-(pyrrolidine-1-yl)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-4-methylphenyl, R3=N-2-(pyrrolidine-1-yl)ethyl, R4=R5=H] Compound 23 The compound was isolated as a TFA salt.

[0129] 1 H NMR (500 MHz, DMSO-d6) δ ppm 1.78 - 1.91 (m, 2 H) 1.93 - 2.06 (m,2 H) 2.37 - 2.40 (m, 3H) 2.97 - 3.10 (m, 2 H) 3.23 - 3.31 (m, 2 H) 3.47 -3.55 (m, 1 H) 3.56 - 3.65 (m, 2 H) 6.94 - 6.98 (m, 1 H) 7.04 - 7.11 (m, 2 H)7.38 - 7.47 (m, 3 H) 7.57 - 7.60 (m, 1 H) 8.17 - 8.23 ​​(m, 1 H) 8.24 - 8.31 (m, 1 H) 9.25 - 9.63 (m, 1 H) 11.67 - 11.83 (m, 1 H) 11.99 - 12.09 (m, 1 H). LCMS: m / z 432 [M+H] + HRMS (ESI) for C 25 H 26 FN5O [M+H] + The calculated value is 432.2194, and the measured value is 432.2197. N-[2-(dimethylamino)ethyl]-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-4-methylphenyl, R3=N-2-(dimethylamino)ethyl, R4=R5=H] Compound 24 The compound was isolated as a TFA salt.

[0130] 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.37 - 2.41 (m, 3 H) 2.78 - 2.88 (m,6 H) 3.17 - 3.24 (m, 2 H) 3.46 - 3.56 (m, 2 H) 6.92 - 6.98 (m, 1 H) 7.05 -7.13 (m, 2 H) 7.38 - 7.46 (m, 3 H) 7.55 - 7.61 (m, 1 H) 8.13 - 8.24 (m, 1 H)8.25 - 8.32 (m, 1 H) 11.59 - 11.85 (m, 1 H) 11.95 - 12.12 (m, 1 H). LCMS: m / z406 [M+H] + HRMS (ESI) for C 23 H 24 FN5O [M+H] + The calculated value is 406.2038, and the measured value is 406.2036. 2-(2-fluoro-4-methylphenyl)-N-[2-(morpholin-4-yl)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-4-methylphenyl, R3=N-2-(morpholin-4-yl)ethyl, R4=R5=H] Compound 25 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.37 - 2.39 (m, 3 H) 2.9 - 4.02 (m,12 H) 6.95 (dd, J=3.43, 1.91 Hz, 1 H) 7.04 - 7.12 (m, 2 H) 7.32 - 7.47 (m, 2H) 7.57 (t, J=2.82 Hz, 1 H) 8.20 (d, J=5.03 Hz, 1 H) 11.47 - 12.21 (m, 2 H). LCMS: m / z 448 [M+H] + HRMS (ESI) for C 25 H 26 FN5O2[M+H] + The calculated value is 448.2144, and the measured value is 448.2132. N-[(1S,2R)-2-aminocyclohexyl]-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-4-methylphenyl, R3=N-(1S,2R)-2-aminocyclohexyl, R4=R5=H] Compound 26 The compound was isolated as a TFA salt.

[0131] 1 H NMR (500 MHz, DMSO-d6) δ ppm 1.30 - 1.45 (m, 2 H) 1.48 - 1.78 (m,6 H) 2.38 (s, 3 H) 4.23 (br. s., 1 H) 6.98 (dd, J=3.43, 1.91 Hz, 1 H) 7.06 -7.15 (m, 2 H) 7.40 (d, J=5.19 Hz, 1 H) 7.42 - 7.49 (m, 3 H) 7.55 - 7.62 (m, 1H) 7.71 (br. s., 2 H) 8.21 (d, J=5.19 Hz, 1 H) 11.74 (br. s., 1 H) 11.98 (d,J=2.14 Hz, 1H). LCMS: m / z 432 [M+H] + HRMS (ESI) for C 25 H 26 FN5O [M+H] + The calculated value is 432.2194, and the measured value is 432.2189. 2-(2-fluoro-4-methylphenyl)-N-(furan-2-ylmethyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-4-methylphenyl, R3=N-(furan-2-ylmethyl), R4=R5=H] Compound 27 1H NMR (500 MHz, DMSO-d6) δ ppm 2.38 (s, 1 H) 4.38 (d, J=5.80 Hz, 1H) 6.20 - 6.25 (m, 1 H) 6.39 (dd, J=3.13, 1.91 Hz, 1 H) 7.03 - 7.11 (m, 1 H)7.37 - 7.47 (m, 1 H) 7.55 - 7.60 (m, 1 H) 8.22 (d, J=5.34 Hz, 1 H) 8.50 (t, J=5.87 Hz, 1 H) 11.64 - 12.14 (m, 1 H). LCMS: m / z 415 [M+H] + HRMS (ESI) for C 24 H 19 FN4O2[M+H] + The calculated value is 415.1565, and the measured value is 415.1569. N-(fluoroethyl)-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-4-methylphenyl, R3=N-(fluoroethyl), R4=R5=H] Compound 28 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.36 - 2.40 (m, 3 H) 3.41 - 3.54 (m,2 H) 4.38 - 4.58 (m, 2 H) 7.00 (dd, J=3.51, 1.83 Hz, 1 H) 7.04 - 7.10 (m, 2H) 7.38 - 7.44 (m, 3 H) 7.54 - 7.56 (m, 1 H) 8.19 (d, J=5.19 Hz, 1 H) 8.24 (t, J=5.64 Hz, 1 H) 11.53 - 12.04 (m, 2 H). LCMS: m / z 381 [M+H] + HRMS (ESI) for C 21 H 18 F2N4O [M+H] + The calculated value is 381.1522, and the measured value is 381.1518. 2-(2-fluoro-4-methylphenyl)-N-[2-(methylamino)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-4-methylphenyl, R3=N-(2-(methylamino)ethyl, R4=R5=H] Compound 29 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.37 - 2.40 (m, 3 H) 2.58 (s, 3 H)3.04 (t, J=5.95 Hz, 2 H) 3.45 (q, J=6.00 Hz, 2 H) 6.96 (dd, J=3.43, 1.91 Hz,1 H) 7.04 - 7.11 (m, 2 H) 7.37 - 7.46 (m, 3 H) 7.55 - 7.60 (m, 1 H) 8.20 (d,J=5.03 Hz, 1 H) 8.26 (t, J=5.64 Hz, 1 H) 8.33 (br. s., 1 H) 11.51 - 12.14 (m,2 H). LCMS: m / z 392 [M+H] + HRMS (ESI) for C 22 H 22 FN5O [M+H] + The calculated value is 392.1881, and the measured value is 392.1878. 2-(2-fluoro-4-methylphenyl)-N-(1-methylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-4-methylphenyl, R3=N-(1-methylpiperidin-4-yl), R4=R5=H] Compound 30 1H NMR (500 MHz, DMSO-d6) δ ppm 1.45 - 1.59 (m, 2 H) 1.72 (d, J=10.37Hz, 2 H) 1.90 (t, J=11.21 Hz, 2 H) 2.15 (s, 3 H) 2.35 - 2.39 (m, 3 H) 2.74(d, J=11.13 Hz, 2 H) 3.56 - 3.68 (m, 1 H) 7.00 (dd, J=3.51, 1.98 Hz, 1 H)7.04 - 7.10 (m, 2 H) 7.31 - 7.43 (m, 3 H) 7.52 - 7.58 (m, 1 H) 7.70 (d, J=7.93 Hz, 1 H) 8.18 (d, J=5.03 Hz, 1 H) 11.53 - 12.01 (m, 2 H). LCMS: m / z 432 [M+H] + HRMS (ESI) for C 25 H 26 FN5O [M+H] + The calculated value is 432.2194, and the measured value is 432.2186. 2-(dibenzo[b,d]thiophen-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=dibenzo[b,d]thiophen-4-yl, R3=R4=R5=H] Compound 31 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.81 (br. s., 1 H) 7.07 (dd, J=3.51,1.83 Hz, 1 H) 7.43 (d, J=5.19 Hz, 1 H) 7.46 - 7.55 (m, 3 H) 7.56 - 7.58 (m, 1H) 7.59 - 7.64 (m, 1 H) 7.96 - 8.02 (m, 1 H) 8.19 (d, J=5.19 Hz, 1 H) 8.36 -8.46 (m, 2 H) 11.71 (br. s., 1 H) 12.13 (d, J=1.83 Hz, 1 H). LCMS: m / z 409 [M+H] + HRMS (ESI) for C 24 H 16N4OS [M+H] + The calculated value is 409.1118, and the measured value is 409.1119. 2-(4-methylnaphth-1-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=4-methylnaphth-1-yl, R3=R4=R5=H] Compound 32 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.73 (s, 3 H) 6.68 (br. s., 1 H) 7.05 (dd, J=3.43, 1.91 Hz, 1 H) 7.23 (br. s., 1 H) 7.40 (d, J=5.19 Hz, 1 H) 7.43 -7.48 (m, 3 H) 7.51 (d, J=2.75 Hz, 1 H) 7.54 - 7.61 (m, 2 H) 7.66 (d, J=8.24Hz, 1 H) 8.09 (d, J=8.39 Hz, 1 H) 8.14 (d, J=5.03 Hz, 1 H) 11.68 (br. s., 1H) 11.98 (br. s., 1 H). LCMS: m / z 367 [M+H] + HRMS (ESI) for C 23 H 18 N4O [M+H] + The calculated value is 367.1554, and the measured value is 367.1545. 2-(3-Fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=3-fluorophenyl, R3=R4=R5=H] Compound 33 1H NMR (500 MHz, DMSO-d6) δ ppm 6.92 (br. s., 1 H) 7.00 (dd, J=3.51,1.83 Hz, 1 H) 7.14 - 7.23 (m, 1 H) 7.34 (d, J=2.59 Hz, 1 H) 7.41 - 7.50 (m, 1H) 7.52 - 7.61 (m, 3 H) 7.62 - 7.66 (m, 1 H) 8.21 (d, J=5.19 Hz, 1 H) 11.70 (br. s., 1 H) 11.81 (br. s., 1 H). LCMS: m / z 321 [M+H] + HRMS (ESI) for C 18 H 13 FN4O[M+H] + The calculated value is 321.1146, and the measured value is 321.1143. 5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-2-[4-(trifluoromethoxy)phenyl]-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=4-(trifluoromethoxy)phenyl, R3=R4=R5=H] Compound 34 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.89 (br. s., 1 H) 7.01 (dd, J=3.51,1.83 Hz, 1 H) 7.37 (d, J=2.59 Hz, 1 H) 7.41 (d, J=8.24 Hz, 1 H) 7.46 (d, J=5.19 Hz, 1 H) 7.51 - 7.57 (m, 1 H) 7.64 (br. s., 1 H) 7.77 - 7.85 (m, 1 H)8.20 (d, J=5.03 Hz, 1 H) 11.69 (br. s., 1 H) 11.83 (d, J=1.98 Hz, 1H). LCMS: m / z 387 [M+H] + HRMS (ESI) for C 19 H 13 F3N4O2[M+H] + The calculated value is 387.1064, and the measured value is 387.106. 2-(1-Benzothiophene-3-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=1-benzothiophene-3-yl, R3=R4=R5=H] Compound 35 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.79 - 6.82 (m, 1 H) 7.03 - 7.05 (m,1 H) 7.37 - 7.41 (m, 1 H) 7.43 - 7.45 (m, 1 H) 7.47 - 7.49 (m, 1 H) 7.54 -7.57 (m, 1 H) 7.58 - 7.61 (m, 1 H) 7.90 - 7.92 (m, 1 H) 8.03 - 8.06 (m, 1 H)8.16 - 8.20 (m, 1 H) 11.66 - 11.71 (m, 1 H) 11.97 - 12.02 (m, 1 H). LCMS: m / z359 [M+H] + HRMS (ESI) for C 20 H 14 N4OS [M+H] + The calculated value is 359.0961, and the measured value is 359.0962; 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2,3-dihydro-1,4-benzodioxin-6-yl, R3=R4=R5=H] Compound 36 1H NMR (500 MHz, DMSO-d6) δ ppm 4.28 (s, 4 H) 6.81 (br. s., 1 H) 6.88 (d, J=8.39 Hz, 1 H) 6.97 (dd, J=3.51, 1.83 Hz, 1 H) 7.18 (dd, J=8.39, 2.14Hz, 1 H) 7.24 (d, J=2.14 Hz, 1 H) 7.27 (d, J=2.74 Hz, 1 H) 7.46 (d, J=5.19Hz, 1 H) 7.51 - 7.52 (m, 1 H) 8.18 (d, J=5.03 Hz, 1 H) 11.58 - 11.67 (m, 2H). LCMS: m / z 361 [M+H] + HRMS (ESI) for C 20 H 16 N4O3[M+H] + The calculated value is 361.1295, and the measured value is 361.1295. 2-(4-fluoro-2-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=4-fluoro-2-methylphenyl, R3=R4=R5=H] Compound 37 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.20 (s, 3 H) 6.73 (br. s., 1 H) 7.01 (dd, J=3.51, 1.98 Hz, 1 H) 7.06 (d, J=2.75 Hz, 1 H) 7.15 (dd, J=10.22, 2.75Hz, 1 H) 7.33 (dd, J=8.46, 6.18 Hz, 1 H) 7.36 - 7.40 (m, 1 H) 7.43 (d, J=2.59Hz, 1 H) 7.52 - 7.54 (m, 1 H) 8.15 (d, J=5.19 Hz, 1 H) 11.66 (br. s., 1 H)11.81 (d, J=1.98 Hz, 1 H). LCMS: m / z 335 [M+H] + HRMS (ESI) for C 19 H 15 FN4O [M+H] +The calculated value is 335.1303, and the measured value is 335.13. 2-(2-fluoro-4-methylphenyl)-4-iodo-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (I) [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-4-methylphenyl, R3=R4=H, R5=iodo] Compound 38 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.35 (s, 3 H) 6.54 (dd, J=3.43, 1.91Hz, 1 H) 7.07 (d, J=7.78 Hz, 1 H) 7.11 (d, J=11.44 Hz, 1 H) 7.17 (br. s., 1H) 7.23 (br. s., 1 H) 7.26 (d, J=5.03 Hz, 1 H) 7.42 (t, J=7.85 Hz, 1 H) 7.51- 7.60 (m, 1 H) 8.29 (d, J=5.03 Hz, 1 H) 11.78 (br. s., 1 H) 11.99 (s, 1 H). LCMS: m / z 461 [M+H] + HRMS (ESI) for C 19 H 14 FIN4O [M+H] + The calculated value is 461.0269, and the measured value is 461.0263. 2-(2-fluoro-4-methylphenyl)-4-bromo-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2-fluoro-4-methylphenyl, R3=R4=H, R5=bromo] Compound 39 1H NMR (500 MHz, DMSO-d6) δ ppm 2.36 (s, 3 H) 6.58 (dd, J=3.43, 1.91Hz, 1 H) 7.08 (d, J=7.78 Hz, 1 H) 7.12 (d, J=11.44 Hz, 1 H) 7.23 (br. s., 1H) 7.25 (d, J=4.88 Hz, 1 H) 7.28 (br. s., 1 H) 7.44 (t, J=7.85 Hz, 1 H) 7.53- 7.58 (m, 1 H) 8.28 (d, J=5.03 Hz, 1 H) 11.79 (br. s., 1 H) 12.00 (s, 1 h). LCMS: m / z 413 [M+H] + HRMS (ESI) for C 19 H 14 FBrN4O [M+H] + The calculated value is 413.0408, and the measured value is 413.0407. 4-Ethyl-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=4-fluoro-2-methylphenyl, R3=R4=R5=ethyl] Compound 40 1 H NMR (500 MHz, DMSO- d 6) δ ppm 1.05 (t, J =7.40 Hz, 3 H) 2.35 (s, 3 H)2.71 (q, J =7.37 Hz, 2 H) 6.51 (dd, J =3.43, 1.91 Hz, 1 H) 6.95 (s, 2 H) 7.02 -7.11 (m, 3 H) 7.44 (t, J =7.93 Hz, 1 H) 7.50 (t, J =1.00 Hz, 1 H) 8.24 (d, J =4.88 Hz, 1 H) 11.28 (s, 1 H) 11.70 (br. s., 1 H). LCMS: m / z 363 [M+H] + HRMS (ESI) for C 21 H19 FN4O [M+H] + The calculated value is 363.1616, and the measured value is 363.1601. 2-(2-fluoro-4-methylphenyl)-4-(propyl-2-yl)-5-(1 H -pyrrolo[2,3- b ]pyridin-4-yl)-1 H -Pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=4-fluoro-2-methylphenyl, R3=R4=H, R5=propyl-2-yl] Compound 41 1 H NMR (500 MHz, DMSO- d 6) δ ppm 1.31 (d, J =7.02 Hz, 6 H) 2.34 (s, 3 H)3.10 (spt, J =7.00 Hz, 1 H) 6.51 (dd, J =3.36, 1.98 Hz, 1 H) 6.89 - 7.14 (m, 5H) 7.39 (t, J =7.93 Hz, 1 H) 7.51 (t, J =2.90 Hz, 1 H) 8.24 (d, J =4.88 Hz, 1 H)11.18 (s, 1 H) 11.71 (br. s., 1 H). LCMS: m / z 377 [M+H] + HRMS (ESI) for C 22 H 21 FN4O[M+H] + The calculated value is 377.1772, and the measured value is 377.1767. Example B Step 8 2-(2,4-Dichlorophenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxynitrile(XIII) At T=0 °C, 60% NaH (1.7 equivalent, 287 mg, 7.17 mmol) in mineral oil was added to a solution of 2-(2,4-dichlorophenyl)-1H-pyrrolo-3-carboxynitrile (1 equivalent, 1.0 g, 4.22 mmol) in dry THF (20 mL). The reaction mixture was stirred at T=0 °C for 20 min, and SEMCl (1.8 equivalent, 1.35 mL, 7.59 mmol) was added. After 10 min at T=0 °C, the reaction was heated at room temperature and stirred for 3 h. Distilled water was added, and the product was extracted with DCM. The organic layer was washed with distilled water and brine, dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by rapid chromatography (hexane / AcOEt9 / 1) to provide the title compound (pale yellow oil, 1.45 g, Y=94%).

[0132] 1 H NMR (500 MHz, DMSO- d 6) δ ppm -0.13 - -0.06 (m, 9 H) 0.65 - 0.75 (m,2 H) 3.19 - 3.31 (m, 2 H) 5.01 - 5.07 (m, 1 H) 5.19 - 5.22 (m, 1 H) 6.64 -6.69 (m, 1 H) 7.24 - 7.29 (m, 1 H) 7.54 - 7.57 (m, 1 H) 7.59 - 7.62 (m, 1 H)7.87 - 7.90 (m, 1 H). LCMS: m / z 367 [M+H] + HRMS (ESI) for C 17 H 21 Cl2N2OSi [M+H] + The calculated value is 367.0795, and the measured value is 367.08; Operating in a similar manner, but using 2-(2-fluoro-4-methylphenyl)-1H-pyrrole-3-carboxynitrile as the starting material, the following compounds were obtained: 2-(2-Fluoro-4-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxynitrile(XIII) 1H NMR (500 MHz, DMSO-d6) δ ppm -0.15 - -0.07 (m, 9 H) 0.66 - 0.72(m, 2 H) 2.40 (s, 3 H) 3.18 - 3.32 (m, 2 H) 5.17 (s, 2 H) 6.65 (d, J=3.20 Hz,1 H) 7.17 - 7.21 (m, 1 H) 7.23 - 7.27 (m, 2 H) 7.40 (t, J=7.78 Hz, 1 H). LCMS: m / z 331 [M+H] + HRMS (ESI) for C 18 H 24 FN2OSi [M+H] + The calculated value is 331.1637, and the measured value is 331.1628. 2-(2,4-Dichlorophenyl)-1-(benzenesulfonyl)-1H-pyrrole-3-carboxynitrile (XIII) At T=0 °C, 60% NaH (1.3 equivalents, 219 mg, 5.49 mmol) in mineral oil was added to a solution of 2-(2,4-dichlorophenyl)-1H-pyrrolo-3-carboxynitrile (1 equivalent, 1.0 g, 4.22 mmol) in dry DMF (10 mL). The reaction mixture was stirred at T=0 °C for 20 min, and benzenesulfonyl chloride (1.2 equivalents, 0.64 mL, 5.06 mmol) was added. The reaction mixture was stirred at T=0 °C for 2.5 h. Distilled water was added at T=0 °C, and the product was extracted with AcOEt. The organic layer was washed with distilled water and brine, dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by rapid chromatography (hexane / AcOEt 9 / 1-hexane / AcOEt 8 / 2) to provide the title compound (white solid, 1.32 g, Y=83%).

[0133] 1H NMR (500 MHz, DMSO-d6) δ ppm 6.96 (d, J=3.51 Hz, 1 H) 7.37 (d, J=8.24 Hz, 1 H) 7.58 (dd, J=8.24, 2.14 Hz, 1 H) 7.60 - 7.66 (m, 4 H) 7.78 (d, J=2.13 Hz, 1 H) 7.81 (tt, J=5.85, 2.76 Hz, 1 H) 7.85 (d, J=3.51 Hz, 1 H). LCMS: m / z 378 [M+H] +HRMS (ESI) for C 17 H 11 Cl2N2O2S [M+H] + The calculated value is 378.9732, and the measured value is 378.9744. Step 9 5-Bromo-2-(2,4-Dichlorophenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxynitrile (XIV) At T=0 °C, 0.5 equivalents of N-bromosuccinimide (349.5 mg, 1.96 mmol) were added to a solution of 2-(2,4-dichlorophenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (1 equivalent, 1.44 g, 3.93 mmol) in MeOH (20 ml) and THF (10 ml). The reaction mixture was stirred at T=0 °C for 30 min, and then 0.5 equivalents of N-bromosuccinimide (349.5 mg, 1.96 mmol) were added. The reaction mixture was stirred at T=0 °C for 1 h followed by 30 min. Distilled water was added, and the product was extracted three times with AcOEt. The organic layer was washed with brine, dried over anhydrous Na₂SO₄, and evaporated to dryness. The crude product was purified by rapid chromatography (hexane / AcOEt 95 / 5) to provide the title compound (clear to pale yellow oil, 1.44 g, Y=82%).

[0134] 1H NMR (500 MHz, DMSO-d6) δ ppm -0.15 - -0.06 (m, 9 H) 0.69 (t, J=8.16 Hz, 2 H) 3.17 - 3.32 (m, 2 H) 5.06 (d, J=11.44 Hz, 1 H) 5.21 (d, J=11.44Hz, 1H) 6.96 (s, 1H) 7.59 - 7.67 (m, 2H) 7.92 (d, J=1.98Hz, 1H). LCMS: m / z444 [M+H] + HRMS (ESI) for C 17 H 20 BrCl2N2OSi [M+H] + The calculated value is 444.99, and the measured value is 444.9915. Operating in a similar manner, but using 2-(2-fluoro-4-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxynitrile as the starting material, the following compounds were obtained: 5-Bromo-2-(2-fluoro-4-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxynitrile (XIV) 1H NMR (500 MHz, DMSO-d6) δ ppm -0.13 - -0.09 (m, 9 H) 0.63 - 0.71(m, 2 H) 2.41 (s, 3 H) 3.17 - 3.27 (m, 2 H) 5.18 (br. s., 2 H) 6.89 - 6.97 (m, 1 H) 7.16 - 7.23 (m, 1 H) 7.25 - 7.32 (m, 1 H) 7.39 - 7.45 (m, 1 H). LCMS: m / z 409 [M+H] + HRMS (ESI) for C 18 H 23 BrFN2OSi [M+H] + The calculated value is 409.0742, and the measured value is 409.0743. 5-Bromo-2-(2,4-dichlorophenyl)-1-(benzenesulfonyl)-1H-pyrrole-3-carboxylonitrile (XIV) LCMS: m / z 454 [M+H] + HRMS (ESI) for C 17 H 10 BrCl2N2O2S [M+H] + The calculated value is 454.9018, and the measured value is 454.9125. Step 10 2-(2,4-Dichlorophenyl)-5-(1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) Under an argon atmosphere, 5-bromo-2-(2,4-dichlorophenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxylonitrile (1 equivalent, 100 mg, 0.22 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborhecyclopentan-2-yl)-1H-pyrazole (1.5 equivalent, 99 mg, 0.34 mmol), Na2CO3 (3 equivalent, 71 mg, 0.67 mmol), degassed 1,4-dioxane (4 ml), and degassed distilled water (1 ml) were added to the reactor. After three vacuum / argon cycles, the catalyst [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride (1:1) (0.1 equivalent, 18 mg, 0.022 mmol) was added. After three vacuum / argon cycles, the reaction mixture was heated at T=100°C for 2 hours. Distilled water was added, and the product was extracted with AcOEt (3 times). The organic layer was washed with distilled water and brine, dried over anhydrous Na₂SO₄, and evaporated to dryness. The crude product was purified by rapid chromatography (DCM / MeOH 98 / 2) to provide the title compound (yellow solid, 43 mg, Y=45%).

[0135] 1H NMR (401 MHz, DMSO-d6) δ ppm -0.12 (s, 9 H) 0.65 (t, J=8.30 Hz, 2H) 1.28 - 1.28 (m, 1 H) 3.10 - 3.21 (m, 2 H) 4.99 (d, J=11.35 Hz, 1 H) 5.21(d, J=11.35 Hz, 1 H) 6.78 (s, 1 H) 7.59 - 7.63 (m, 1 H) 7.63 - 7.67 (m, 1 H)7.78 (s, 1 H) 7.91 (d, J=1.71 Hz, 1 H) 8.02 (s, 1 H). LCMS: m / z 433 [M+H] + HRMS (ESI) for C 20 H 23 Cl2N4OSi [M+H] + The calculated value is 433.1013, and the measured value is 433.1014. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(2,4-Dichlorophenyl)-5-(3-methyl-1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) 1H NMR (500 MHz, DMSO-d6) δ ppm -0.13 (s, 9 H) 0.61 (t, J=8.31 ​​Hz, 2H) 2.15 - 2.29 (m, 3 H) 3.07 (q, J=7.83 Hz, 2 H) 4.91 (d, J=11.29 Hz, 1 H)5.09 (d, J=10.98 Hz, 1 H) 6.61 - 6.72 (m, 1 H) 7.57 - 7.68 (m, 3 H) 7.84 -7.96 (m, 2 H) 12.72 - 12.97 (m, 1 H). LCMS: m / z 447 [M+H] + HRMS (ESI) for C 21 H 25 Cl2N4OSi [M+H] + The calculated value is 447.1169, and the measured value is 447.1173. 5-(2-amino-1,3-thiazo-4-yl)-2-(2,4-dichlorophenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) LCMS: m / z 465 [M+H] + HRMS (ESI) for C 20 H 23 Cl2N4OSSi [M+H] + The calculated value is 465.0733, and the measured value is 465.0764. 2-(2,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) LCMS: m / z 483 [M+H] + HRMS (ESI) for C 24 H 25 Cl2N4OSi [M+H] + The calculated value is 483.1169, and the measured value is 483.1185. 2-(2,4-Dichlorophenyl)-5-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) LCMS: m / z 484 [M+H] + HRMS (ESI) for C 23 H 24 Cl2N5OSi [M+H] + The calculated value is 484.1122, and the measured value is 484.1157. 2-(2,4-Dichlorophenyl)-5-[3-(trifluoromethyl)-1H-pyrazol-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) LCMS: m / z 501 [M+H] + HRMS (ESI) for C 21 H 22 Cl2F3N4OSi [M+H] + The calculated value is 501.0887, and the measured value is 501.0894. Operating in a similar manner, but using 5-bromo-2-(2,4-dichlorophenyl)-1-(benzenesulfonyl)-1H-pyrrole-3-carboxynitrile as the starting material, the following compounds were obtained: 5-(6-aminopyrimidin-4-yl)-2-(2,4-dichlorophenyl)-1-(benzenesulfonyl)-1H-pyrrolo-3-carboxynitrile (XV) 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.60 (d, J=0.91 Hz, 1 H) 7.12 (s, 1H) 7.14 (br. s., 1 H) 7.41 (d, J=8.24 Hz, 1 H) 7.56 (dd, J=8.31, 2.06 Hz, 1H) 7.58 - 7.63 (m, 2 H) 7.76 (dd, J=8.46, 0.99 Hz, 2 H) 7.78 (d, J=1.98 Hz, 1H) 7.80 (t, J=7.50 Hz, 0 H) 8.40 (d, J=0.92 Hz, 1 H). LCMS: m / z 470 [M+H] + HRMS (ESI) for C 21 H 14 Cl2N5O2S [M+H] + The calculated value is 470.0240, and the measured value is 470.0256. Operating in a similar manner, but using 5-bromo-2-(2-fluoro-4-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxynitrile as the starting material, the following compounds were obtained: 2-(2-Fluoro-4-methylphenyl)-5-(1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) 1 H NMR (500 MHz, DMSO-d6) δ ppm -0.15 - -0.12 (m, 9 H) 0.59 - 0.69(m, 2 H) 2.41 (s, 3 H) 3.09 - 3.19 (m, 2 H) 5.14 (br. s., 2 H) 6.76 (s, 1 H)7.22 (d, J=8.24 Hz, 1 H) 7.29 (d, J=10.83 Hz, 1 H) 7.43 (t, J=7.85 Hz, 1 H)7.77 (s, 1 H) 8.01 (s, 1 H) 13.14 (br. s., 1 H). LCMS: m / z 397 [M+H] + HRMS (ESI) for C 21 H 26 FN4OSi [M+H] + The calculated value is 397.1855, and the measured value is 397.1857. 5-(3,5-Dimethyl-1H-pyrazol-4-yl)-2-(2-fluoro-4-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) 1 H NMR (500 MHz, DMSO-d6) δ ppm -0.16 (s, 9 H) 0.46 - 0.58 (m, 2 H)2.02 (s, 3 H) 2.10 (s, 3 H) 2.41 (s, 3 H) 2.86 - 3.00 (m, 2 H) 4.93 (s, 2 H)6.56 (s, 1 H) 7.20 (d, J=7.63 Hz, 1 H) 7.26 (d, J=10.98 Hz, 1 H) 7.46 (t, J=7.78 Hz, 1 H) 12.50 (s, 1 H). LCMS: m / z 425 [M+H]+ HRMS (ESI) for C 23 H 30 FN4OSi [M+H] + The calculated value is 425.2168, and the measured value is 425.2172. 2-(2-Fluoro-4-methylphenyl)-5-(1-methyl-1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) 1 H NMR (500 MHz, DMSO-d6) δ ppm -0.13 (s, 9 H) 0.65 (dd, J=9.00, 7.63Hz, 2 H) 2.41 (s, 3 H) 3.08 - 3.19 (m, 2 H) 3.88 (s, 3 H) 5.14 (br. s., 2 H)6.74 (s, 1 H) 7.22 (dsxt, J=7.78, 0.80, 0.80, 0.80, 0.80, 0.80 Hz, 1 H) 7.29(d, J=10.98 Hz, 1 H) 7.43 (t, J=7.85 Hz, 1 H) 7.71 (d, J=0.61Hz, 1H) 7.96 (s, 1 H). LCMS: m / z 411 [M+H] + HRMS (ESI) for C 22 H 28 FN4OSi [M+H] + The calculated value is 411.2011, and the measured value is 411.2011. 2-(2-Fluoro-4-methylphenyl)-5-(3-methyl-1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) LCMS: m / z 411 [M+H] + HRMS (ESI) for C 22 H 28 FN4OSi [M+H] + The calculated value is 411.2011, and the measured value is 411.2035. 2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XV) 1 H NMR (500 MHz, DMSO-d6) δ ppm -0.27 - -0.19 (m, 9 H) 0.40 - 0.55(m, 2 H) 2.43 (s, 3 H) 2.91 - 3.01 (m, 2 H) 5.23 (br. s., 2 H) 6.53 (dd, J=3.43, 1.91 Hz, 1 H) 7.01 (s, 1 H) 7.21 - 7.28 (m, 2 H) 7.32 (d, J=10.83 Hz, 1H) 7.54 - 7.62 (m, 2 H) 8.30 (d, J=4.88 Hz, 1 H) 11.90 (br. s., 1 H). LCMS: m / z447 [M+H] + HRMS (ESI) for C 25 H 28 FN4OSi [M+H] + The calculated value is 447.2011, and the measured value is 447.2020. Step 11 2-(2,4-Dichlorophenyl)-5-(1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (XVI) To a solution of 2-(2,4-dichlorophenyl)-5-(1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (1 equivalent, 220 mg, 0.51 mmol) in toluene (7 mL), acetaldehyde oxime (20 equivalents, 0.62 mL, 10.16 mmol) and InCl3 (0.1 equivalents, 11 mg, 0.051 mmol) were added. The reaction mixture was heated at T = 100 °C for 4 hours. Distilled water was added, and the product was extracted with AcOEt (3 times). The organic layer was washed with distilled water and brine, dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by rapid chromatography (DCM / MeOH 95 / 5) to provide the title compound (white solid, 106 g, Y = 47%).

[0136] 1H NMR (500 MHz, DMSO-d6) δ ppm -0.14 - -0.10 (m, 8 H) 0.59 - 0.69(m, 2 H) 3.05 - 3.17 (m, 2 H) 4.81 (d, J=11.13 Hz, 1 H) 5.06 (d, J=11.29 Hz,1 H) 6.71 - 6.76 (m, 2 H) 7.18 (br. s., 1 H) 7.38 - 7.42 (m, 1 H) 7.47 - 7.50 (m, 2 H) 7.70 (d, J=2.14 Hz, 1 H) 7.92 (d, J=4.27 Hz, 1 H) 13.05 (br. s., 1H). LCMS: m / z 451 [M+H] + HRMS (ESI) for C 20 H 25 Cl2N4O2Si [M+H] + The calculated value is 451.1119, and the measured value is 451.1119. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(2,4-Dichlorophenyl)-5-(3-methyl-1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (XVI) 1 H NMR (500 MHz, DMSO-d6) δ ppm -0.22 - -0.04 (m, 9 H) 0.61 (t, J=8.39 Hz, 2 H) 2.26 (br. s., 3 H) 2.89 - 3.13 (m, 2 H) 4.73 (d, J=10.98 Hz, 1H) 4.95 (d, J=10.98 Hz, 1 H) 6.48 - 6.69 (m, 1 H) 6.73 (br. s., 1 H) 7.22 (br. s., 1 H) 7.40 (d, J=8.20 Hz, 1 H) 7.47 (dd, J=8.20, 2.10 Hz, 1 H) 7.68(d, J=2.14 Hz, 1 H) 12.46 - 13.03 (m, 1 H). LCMS: m / z 465 [M+H] + HRMS (ESI) for C 21 H27 Cl2N4O2Si [M+H] + The calculated value is 465.1275, and the measured value is 465.1289. 5-(2-amino-1,3-thiazo-4-yl)-2-(2,4-dichlorophenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxynitrile (XVI) LCMS: m / z 483 [M+H] + HRMS (ESI) for C 20 H 24 Cl2N4O2SSi [M+H] + The calculated value is 483.0839, and the measured value is 483.0852. 2-(2,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XVI) LCMS: m / z 501 [M+H] + HRMS (ESI) for C 24 H 27 Cl2N4O2Si [M+H] + The calculated value is 501.1275, and the measured value is 501.1268. 2-(2,4-Dichlorophenyl)-5-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XVI) LCMS: m / z 502 [M+H] + HRMS (ESI) for C 23 H 26 Cl2N5O2Si [M+H] + The calculated value is 502.1227, and the measured value is 502.1236. 2-(2,4-Dichlorophenyl)-5-[3-(trifluoromethyl)-1H-pyrazol-4-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (XVI) LCMS: m / z 519 [M+H] + HRMS (ESI) for C21 H 24 Cl2F3N4O2Si [M+H] + The calculated value is 519.0992, and the measured value is 519.0996. 5-(6-aminopyrimidin-4-yl)-2-(2,4-dichlorophenyl)-1-(benzenesulfonyl)-1H-pyrrole-3-carboxamide (XVI) LCMS: m / z 488 [M+H] + HRMS (ESI) for C 21 H 16 Cl2N5O3S [M+H] + The calculated value is 488.0345, and the measured value is 488.0352. 2-(2-Fluoro-4-methylphenyl)-5-(1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (XVI) LCMS: m / z 415 [M+H] + HRMS (ESI) for C 21 H 28 FN4O2Si [M+H] + The calculated value is 415.1960, and the measured value is 415.1975. 5-(3,5-Dimethyl-1H-pyrazol-4-yl)-2-(2-fluoro-4-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (XVI) 1 H NMR (500 MHz, DMSO-d6) δ ppm -0.15 (s, 9 H) 0.42 - 0.60 (m, 2 H)2.05 (br. s., 6 H) 2.36 (s, 3 H) 2.89 (q, J=8.80 Hz, 2 H) 4.56 - 4.95 (m, 2H) 6.48 (s, 1 H) 6.69 (br. s., 1 H) 7.02 (br. s., 1 H) 7.03 - 7.08 (m, 2 H) 7.26 (t, J=7.85 Hz, 1 H) 12.38 (br. s., 1 H). LCMS: m / z 443 [M+H] + HRMS (ESI) for C23 H 32 FN4O2Si [M+H] + The calculated value is 443.2273, and the measured value is 443.2272. 2-(2-Fluoro-4-methylphenyl)-5-(1-methyl-1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (XVI) 1 H NMR (500 MHz, DMSO-d6) δ ppm -0.12 (s, 9 H) 0.64 (t, J=8.31 ​​Hz, 2H) 2.37 (s, 3 H) 2.97 - 3.09 (m, 1 H) 3.12 (t, J=8.24 Hz, 1 H) 3.88 (s, 3 H)4.80 - 4.98 (m, 1 H) 4.98 - 5.18 (m, 1 H) 6.68 (s, 1 H) 6.70 (br. s., 1 H)7.04 (br. s., 1 H) 7.05 - 7.11 (m, 2 H) 7.23 (t, J=7.85 Hz, 1 H) 7.61 (d, J=0.61 Hz, 1 H) 7.86 (s, 1 H). LCMS: m / z 429 [M+H] + HRMS (ESI) for C 22 H 30 FN4O2Si [M+H] + The calculated value is 429.2117, and the measured value is 429.2116. 2-(2-Fluoro-4-methylphenyl)-5-(3-methyl-1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (XVI) LCMS: m / z 429 [M+H] + HRMS (ESI) for C 22 H 30 FN4O2Si [M+H] + The calculated value is 429.2117, and the measured value is 429.2116. 2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo-3-carboxamide (XVI) 1 H NMR (500 MHz, DMSO-d6) δ ppm -0.21 - -0.17 (m, 9 H) 0.55 (t, J=8.39 Hz, 2 H) 2.38 (s, 3 H) 2.87 - 3.10 (m, 2 H) 4.95 - 5.22 (m, 2 H) 6.66(br. s., 0 H) 6.80 (br. s., 1 H) 7.09 (d, J=9.15 Hz, 2 H) 7.24 (d, J=5.03 Hz, 1 H) 7.31 - 7.41 (m, 2 H) 7.54 - 7.58 (m, 1 H) 8.26 (d, J=4.88 Hz, 1H) 11.80 (br. s., 1 H). LCMS: m / z 465 [M+H] + HRMS (ESI) for C 25 H 30 FN4O2Si [M+H] + The calculated value is 465.2117, and the measured value is 465.2132. Step 12 5-(6-aminopyrimidin-4-yl)-2-(2,4-dichlorophenyl)-1H-pyrrolo-3-carboxamide [R1=6-aminopyrimidin-4-yl, R2=2,4-dichlorophenyl, R3=R4=R5=H] Compound 42 To a solution of 5-(6-aminopyrimidin-4-yl)-2-(2,4-dichlorophenyl)-1-(benzenesulfonyl)-1H-pyrrolo-3-carboxamide (1 equivalent, 100 mg, 0.20 mmol) in THF (2.3 mL) and H₂O (1.8 mL), LiOH (4 equivalents, 0.8 mmol, 33.5 mg) was added. The reaction mixture was stirred under reflux for 4 hours. The solvent was partially removed under reduced pressure, and 2N HCl was added to the mixture. The reaction was stirred at room temperature for 30 minutes, and the title compound (white solid, 67 mg, Y = 95%) was collected by filtration.

[0137] 1H NMR (500 MHz, DMSO-d6) δ ppm 6.65 (s, 1 H) 6.76 (br. s., 1 H) 6.91 (br. s., 2 H) 7.29 (s, 1 H) 7.35 (br. s., 1 H) 7.40 - 7.47 (m, 2 H) 7.65 (d,J=1.68 Hz, 1 H) 8.34 (s, 1 H) 12.09 (br. s., 1 H). LCMS: m / z 348 [M+H] + HRMS (ESI) for C 15 H 12 Cl2N5O [M+H] + The calculated value is 348.0414, and the measured value is 348.0424. 2-(2,4-Dichlorophenyl)-5-(1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide [R1=1H-pyrazol-4-yl, R2=2,4-dichlorophenyl, R3=R4=R5=H] Compound 43 To a solution of 2-(2,4-dichlorophenyl)-5-(1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (1 equivalent, 100 mg, 0.22 mmol) in DCM (4.9 mL), TFA (75 equivalents, 16.5 mmol, 1.26 mL) was added. The reaction mixture was stirred at room temperature for 5 hours. The solvent was removed under reduced pressure, and the crude product was treated three times with toluene. In the same reactor, 2-(2,4-dichlorophenyl)-1-(hydroxymethyl)-5-(1 H -pyrazole-4-yl)-1 H 3-pyrrole-3-carboxamide was dissolved in 95% EtOH (8.5 ml), and 30%-32% ammonium hydroxide solution (1.2 ml) was added. The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the solid was washed five times with distilled water (to remove CF3COO). - NH4 + The solution was washed three times with DCM / Et2O 1 / 1 to give the title compound (pale yellow solid, 31 mg, Y = 44%).

[0138] 1H NMR (500 MHz, DMSO-d6) δ ppm 6.65 (br. s., 1 H) 6.67 (d, J=2.6 Hz,1 H) 7.09 (br. s., 1 H) 7.40 - 7.48 (m, 2 H) 7.66 (dd, J=1.4, 0.8 Hz, 1 H)7.73 (br. s., 1 H) 7.93 (br. s., 1 H) 11.46 (s, 1 H) 12.84 (br. s., 1 H). LCMS: m / z 321 [M+H] + HRMS (ESI) for C 14 H 11 Cl2N4O [M+H] + The calculated value is 321.0305, and the measured value is 321.0305. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(2,4-Dichlorophenyl)-5-(3-methyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide [R1=3-methyl-1H-pyrazol-4-yl, R2=2,4-dichlorophenyl, R3=R4=R5=H] Compound 44 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.61 (br. s., 1 H) 6.64 (br. s., 2 H)7.20 (br. s., 1 H) 7.44 (d, J=1.2 Hz, 2 H) 7.65 (s, 1 H) 11.15 - 11.47 (m, 1H) 12.30 - 12.76 (m, 1H). LCMS: m / z 335 [M+H] + HRMS (ESI) for C 15 H 13 Cl2N4O [M+H] + The calculated value is 335.0461, and the measured value is 335.0464. 5-(2-amino-1,3-thiazolyl-4-yl)-2-(2,4-dichlorophenyl)-1H-pyrrole-3-carboxamide [R1=2-amino-1,3-thiazolyl-4-yl, R2=2,4-dichlorophenyl, R3=R4=R5=H] Compound 45 1H NMR (500 MHz, DMSO-d6) δ ppm 6.70 (br. s., 1 H) 6.75 (s, 1 H) 6.83 (d, J=2.59 Hz, 1 H) 7.19 (br. s., 1 H) 7.42 - 7.45 (m, 1 H) 7.45 - 7.47 (m, 1H) 7.67 (d, J=1.98 Hz, 1 H) 11.70 (br. s., 1 H). LCMS: m / z 353 [m+H] + HRMS (ESI) for C 14 H 11 Cl2N4OS [M+H] + The calculated value is 353.0025, and the measured value is 353.0023; 2-(2,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl, R2=2,4-dichlorophenyl, R3=R4=R5=H] Compound 46 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.78 (br. s., 1 H) 7.02 (dd, J=3.5,1.8 Hz, 1 H) 7.36 (d, J=5.2 Hz, 1 H) 7.43 - 7.52 (m, 3 H) 7.53 - 7.59 (m, 2H) 7.70 (d, J=2.0 Hz, 1 H) 8.18 (d, J=5.0 Hz, 1 H) 9.50 - 9.51 (m, 1 H) 11.69 (br. s., 1 H) 11.98 (d, J=1.7 Hz, 1 H). LCMS: m / z 371 [M+H] + HRMS (ESI) for C 18 H 12 Cl2N4O [M+H] + The calculated value is 371.0461, and the measured value is 371.0462. 2-(2,4-Dichlorophenyl)-5-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-pyrrole-3-carboxamide [R1=1H-pyrazolo[3,4-b]pyridin-4-yl, R2=2,4-dichlorophenyl, R3=R4=R5=H] Compound 47 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.88 (br. s., 1 H) 7.46 (d, J=4.9 Hz,1 H) 7.48 - 7.51 (m, 1 H) 7.51 - 7.54 (m, 1 H) 7.59 (br. s., 1 H) 7.67 (d, J=2.6 Hz, 1 H) 7.72 (d, J=2.0 Hz, 1 H) 8.46 (d, J=4.9 Hz, 1 H) 8.67 (d, J=1.1Hz, 1 H) 12.23 (br. s., 1 H) 13.68 (s, 1 H). LCMS: m / z 372 [M+H] + HRMS (ESI) for C 17 H 12 Cl2N5O [M+H] + The calculated value is 372.0414, and the measured value is 372.0417. 2-(2,4-Dichlorophenyl)-5-[3-(trifluoromethyl)-1H-pyrazol-4-yl]-1H-pyrrole-3-carboxamide [R1=3-(trifluoromethyl)-1H-pyrazol-4-yl, R2=2,4-dichlorophenyl, R3=R4=R5=H] Compound 48 1 H NMR (500 MHz, DMSO-d6) δ ppm 6.68 (d, J=1.7 Hz, 2 H) 7.22 (br. s.,1 H) 7.41 - 7.50 (m, 2 H) 7.67 (dd, J=1.7, 0.6 Hz, 1 H) 8.15 (s, 1 H) 11.53 (br. s., 1 H) 13.61 (br. s., 1 H). LCMS: m / z 389 [M+H] + HRMS (ESI) for C 15 H 10 Cl2F3N4O [M+H] + The calculated value is 389.0178, and the measured value is 389.0184. 2-(2-fluoro-4-methylphenyl)-5-(1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide [R1=1H-pyrazol-4-yl, R2=2-fluoro-4-methylphenyl, R3=R4=R5=H] Compound 49 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.39 (s, 3 H) 6.65 (br. s, 1 H) 6.66 (d, J=2.6 Hz, 1 H) 7.04 (br. s., 1 H) 7.05 - 7.12 (m, 2 H) 7.37 (t, J=7.9 Hz,1 H) 7.78 (s, 1 H) 7.98 (s, 1 H) 11.38 (br. s., 1 H) 12.86 (br. s., 1 H). LCMS: m / z 285 [m+H] + HRMS (ESI) for C 15 H 14 FN4O [M+H] + The calculated value is 285.1146, and the measured value is 285.1147. 5-(3,5-Dimethyl-1H-pyrazol-4-yl)-2-(2-fluoro-4-methylphenyl)-1H-pyrrole-3-carboxamide [R1=3,5-dimethyl-1H-pyrazol-4-yl, R2=2-fluoro-4-methylphenyl, R3=R4=R5=H] Compound 50 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.20 (br. s., 3 H) 2.25 (br. s., 3 H)2.34 (s, 3 H) 6.43 (d, J=2.7 Hz, 1 H) 6.62 (br. s., 1 H) 6.98 - 7.04 (m, 2 H)7.07 (br. s., 1 H) 7.35 (t, J=8.0 Hz, 1 H) 10.97 (d, J=2.0 Hz, 1 H) 12.24 (s,1 H). LCMS: m / z 313 [M+H] + HRMS (ESI) for C 17 H 18 FN4O [M+H] + The calculated value is 313.1459, and the measured value is 313.1456. 2-(2-fluoro-4-methylphenyl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide [R1=1-methyl-1H-pyrazol-4-yl, R2=2-fluoro-4-methylphenyl, R3=R4=R5=H] Compound 51 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.35 (s, 3 H) 3.84 (s, 3 H) 6.60 (d,J=2.7 Hz, 1 H) 6.63 (br. s., 1 H) 7.01 (br. s., 1 H) 7.03 (d, J=7.0 Hz, 1 H)7.05 (d, J=10.4 Hz, 1 H) 7.33 (t, J=7.9 Hz, 1 H) 7.68 (d, J=0.6 Hz, 1 H) 7.88 (s, 1 H) 11.37 (br. s., 1 H). LCMS: m / z 299 [M+H] + HRMS (ESI) for C 16 H 16 FN4O [M+H] + The calculated value is 299.1303, and the measured value is 299.1299. 2-(2-fluoro-4-methylphenyl)-5-(3-methyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide [R1=3-methyl-1H-pyrazol-4-yl, R2=2-fluoro-4-methylphenyl, R3=R4=R5=H] Compound 52 1 H NMR (500 MHz, DMSO-d6) δ ppm 2.35 (s, 6 H) 6.51 - 6.68 (m, 2 H)7.00 - 7.07 (m, 2 H) 7.10 (br. s., 1 H) 7.33 (t, J=7.9 Hz, 1 H) 7.75 (br. s.,1 H) 11.23 (br. s., 1 H) 12.18 - 12.82 (m, 1 H). LCMS: m / z 299 [M+H] + HRMS (ESI) for C 16 H 16 FN4O [M+H] + The calculated value is 299.1303, and the measured value is 299.1299. 2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl), R2=2-fluoro-4-methylphenyl, R3=R4=R5=H] Compound 53 1 H NMR (500 MHz, DMSO- d 6) δ ppm 2.38 (s, 3 H) 6.81 (br. s., 1 H) 7.02- 7.15 (m, 3 H) 7.38 - 7.44 (m, 1 H) 7.47 - 7.57 (m, 3 H) 7.63 (t, J =2.90 Hz, 1 H) 8.26 (d, J =5.49 Hz, 1 H) 11.89 - 12.15 (m, 2 H). LCMS: m / z 335 [M+H] + HRMS (ESI) for C 19 H 16 FN4O [M+H] + The calculated value is 335.1303, and the measured value is 335.1302. Example C Step 13 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(2,4-dichlorophenyl)-1H-pyrrolo-3-carboxynitrile (XVIII) At T=0 °C, 60% NaH (1.8 equivalent, 92 mg, 2.29 mmol) in mineral oil was added to a solution of 2-(2,4-dichlorophenyl)-1H-pyrrolo-3-carboxynitrile (1 equivalent, 300 mg, 1.27 mmol) in dry THF (6 mL). The reaction mixture was stirred at T=0 °C for 20 min, and (2-bromo-ethoxy)-tert-butyl-dimethylsilane (XVII) (1.8 equivalent, 0.49 mL, 2.29 mmol) was added. After 10 min at T=0 °C, the reaction was heated at room temperature and stirred for 6 h. Distilled water was added, and the product was extracted with DCM. The organic layer was washed with distilled water and brine, dried over anhydrous Na₂SO₄, and evaporated to dryness. The crude product was purified by rapid chromatography (hexane / AcOEt 9 / 1) to give the title compound (pale yellow oil, 336 mg, Y=67%).

[0139] 1H NMR (500 MHz, DMSO-d6) δ ppm -0.14 - -0.08 (m, 6 H) 0.73 - 0.80(m, 9 H) 3.54 - 3.78 (m, 3 H) 3.89 - 3.97 (m, 1 H) 6.63 (d, J=3.05 Hz, 1 H)7.14 (d, J=3.05 Hz, 1 H) 7.52 (d, J=8.39 Hz, 1 H) 7.63 (dd, J=8.24, 2.14 Hz, 1 H) 7.89 (d, J=2.14 Hz, 1 H). LCMS: m / z 395 [M+H] + HRMS (ESI) for C 19 H 25 Cl2N2OSi[M+H] + The calculated value is 395.1108, and the measured value is 395.1110. By operating in a similar manner, but using appropriately substituted starting materials as intermediates (XVII), the following compounds were obtained: 2-(2,4-Dichlorophenyl)-1-(3,3,3-trifluoropropyl)-1H-pyrrolo-3-carboxynitrile (XVIII) LCMS: m / z 333 [M+H] + HRMS (ESI) for C 14 H9Cl2F3N2[M+H] + The calculated value is 333.0168, and the measured value is 333.0172. 2-(2,4-Dichlorophenyl)-1-methyl-1H-pyrrole-3-carboxynitrile (XVIII) LCMS: m / z 251 [M+H] + HRMS (ESI) for C 12 H8Cl2N2[M+H] + The calculated value is 251.0137, and the measured value is 251.0139. 2-(2,4-Dichlorophenyl)-1-ethyl-1H-pyrrole-3-carboxynitrile (XVIII) LCMS: m / z 265 [M+H] + HRMS (ESI) for C 13 H 10 Cl2N2[M+H]+ The calculated value is 265.0294, and the measured value is 265.0297. Step 14 5-Bromo-2-(2,4-dichlorophenyl)-1-(2-hydroxyethyl)-1H-pyrrole-3-carboxynitrile (XIX) At T=0 °C, 0.5 equivalents of N-bromosuccinimide (74.5 mg, 0.42 mmol) were added to a solution of 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(2,4-dichlorophenyl)-1H-pyrrolo-3-carboxynitrile (1 equivalent, 330 mg, 0.84 mmol) in MeOH (4 ml) and THF (2 ml). The reaction mixture was stirred at T=0 °C for 30 minutes, and then 0.5 equivalents of N-bromosuccinimide (74.5 mg, 0.42 mmol) were added. The reaction mixture was stirred at T=0 °C for 1 hour and 30 minutes. Distilled water was added, and the product was extracted three times with AcOEt. The organic layer was washed with brine, dried over anhydrous Na₂SO₄, and evaporated to dryness. The crude product was purified by rapid chromatography (hexane / AcOEt 95 / 5) to provide the title compound (clear to pale yellow oil, 360 mg, Y=48%).

[0140] LCMS: m / z 358 [M+H] + HRMS (ESI) for C 13 H 10 BrCl2N2O [M+H] + The calculated value is 358.9348, and the measured value is 358.9352. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 5-Bromo-2-(2,4-dichlorophenyl)-1-(3,3,3-trifluoropropyl)-1H-pyrrolo-3-carboxylonitrile (XIX) LCMS: m / z 410 [M+H] + HRMS (ESI) for C 14 H9BrCl2F3N2[M+H] + The calculated value is 410.9273, and the measured value is 410.9274. 5-Bromo-2-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-3-carboxylonitrile (XIX) LCMS: m / z 328 [M+H]+ HRMS (ESI) for C 12 H7BrCl2N2[M+H] + The calculated value is 328.9242, and the measured value is 328.9240. 5-Bromo-2-(2,4-dichlorophenyl)-1-ethyl-1H-pyrrole-3-carboxylonitrile (XIX) LCMS: m / z 342 [M+H] + HRMS (ESI) for C 13 H9BrCl2N2[M+H] + The calculated value is 342.9399, and the measured value is 342.9398. Step 15 2-(2,4-Dichlorophenyl)-1-(2-hydroxyethyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxylonitrile (XX) Under an argon atmosphere, 5-bromo-2-(2,4-dichlorophenyl)-1-(2-hydroxyethyl)-1H-pyrrolo-3-carboxylonitrile (1 equivalent, 140 mg, 0.39 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborphane-2-yl)-1H-pyrrolo[2,3-b]pyridine (1.5 equivalent, 142 mg, 0.58 mmol), Na2CO3 (3 equivalent, 124 mg, 1.17 mmol), degassed 1,4-dioxane (4 ml), and degassed distilled water (1 ml) were added to the reactor. After three vacuum / argon cycles, the catalyst [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (1:1) (0.1 equivalent, 32 mg, 0.039 mmol) was added. After three vacuum / argon cycles, the reaction mixture was heated at T=100°C for 3 hours. Distilled water was added, and the product was extracted with AcOEt (3 times). The organic layer was washed with distilled water and brine, dried over anhydrous Na₂SO₄, and evaporated to dryness. The crude product was purified by rapid chromatography (AcOEt) to provide the title compound (yellow solid, 110 mg, Y=71%).

[0141] 1H NMR (500 MHz, DMSO-d6) δ ppm 3.01 (quind, J=11.74, 11.74, 11.74,11.74, 6.10 Hz, 2 H) 3.77 (dt, J=14.03, 6.86 Hz, 1 H) 3.99 - 4.07 (m, 1 H)4.63 (t, J=5.57 Hz, 1 H) 6.42 - 6.44 (m, 1 H) 6.89 (s, 1 H) 7.18 (d, J=5.0Hz, 1 H) 7.59 - 7.61 (m, 1 H) 7.67 - 7.69 (m, 1 H) 7.74 - 7.72 (m, 1H) 7.94 (d, J=2.0 Hz, 1 H) 8.30 (d, J=5.0 Hz, 1 H) 11.91 (br. s., 1 H). LCMS: m / z 397[M+H] + HRMS (ESI) for C 20 H 15 Cl2N4O [M+H] + The calculated value is 397.0618, and the measured value is 397.0623. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(2,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-(3,3,3-trifluoropropyl)-1H-pyrrolo-3-carboxylonitrile (XX) LCMS: m / z 449 [M+H] + HRMS (ESI) for C 21 H 14 Cl2F3N4[M+H] + The calculated value is 449.0542, and the measured value is 449.0541. 2-(2,4-Dichlorophenyl)-1-methyl-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxylonitrile (XX) LCMS: m / z 367 [M+H] + HRMS (ESI) for C 19 H 12 Cl2N4[M+H] + The calculated value is 367.0512, and the measured value is 367.0513; 2-(2,4-Dichlorophenyl)-1-ethyl-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxylonitrile (XX) LCMS: m / z 381 [M+H] + HRMS (ESI) for C 20 H 14 Cl2N4[M+H] + The calculated value is 381.0668, and the measured value is 381.0670. Step 15 2-(2,4-Dichlorophenyl)-1-(2-hydroxyethyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl), R2=2,4-dichlorophenyl, R3=R5=H, R4=2-hydroxyethyl] Compound 54 To a solution of 2-(2,4-dichlorophenyl)-1-(2-hydroxyethyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxynitrile (1 equivalent, 100 mg, 0.25 mmol) in toluene (3.6 mL), acetaldehyde oxime (20 equivalents, 0.307 mL, 5.05 mmol) and InCl3 (0.1 equivalents, 5.6 mg, 0.025 mmol) were added. The reaction mixture was heated at T = 100 °C for 1 hour. Distilled water was added, and the product was extracted with AcOEt (3 times). The organic layer was washed with distilled water and brine, dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by rapid chromatography (DCM / EtOH 95 / 5) to provide the title compound (white solid, 21 mg, Y = 20%).

[0142] 1H NMR (500 MHz, DMSO-d6) δ ppm 2.94 - 3.07 (m, 2 H) 3.68 (dt, J=14.2, 7.1 Hz, 1 H) 3.88 - 3.97 (m, 1 H) 6.53 (dd, J=3.4, 1.8 Hz, 1 H) 6.74(br. s., 1 H) 6.93 (s, 1 H) 7.18 (d, J=5.0 Hz, 1 H) 7.33 (br. s., 1 H) 7.50 -7.52 (m, 1 H) 7.53 - 7.55 (m, 1 H) 7.57 - 7.60 (m, 1 H) 7.75 (d, J=2.0 Hz, 1H) 8.30 (d, J=5.0 Hz, 1 H) 11.91 (br. s., 1 H). LCMS: m / z 415 [M+H] + HRMS (ESI) for C 20 H 17 Cl2N4O2[M+H] + The calculated value is 415.0723, and the measured value is 415.0722. By operating in a similar manner, but using appropriately substituted starting materials, the following compounds were obtained: 2-(2,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-(3,3,3-trifluoropropyl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl), R2=2,4-dichlorophenyl, R3=R5=H, R4=3,3,3-trifluoropropyl] Compound 55 1H NMR (500 MHz, DMSO-d6) δ ppm 1.99 - 2.17 (m, 2 H) 3.88 - 3.97 (m,1 H) 4.11 - 4.20 (m, 1 H) 6.51 (dd, J=3.4, 1.9 Hz, 1 H) 6.80 (br. s., 1 H)6.97 (s, 1 H) 7.14 (d, J=4.9 Hz, 1 H) 7.39 (br. s., 1 H) 7.53 - 7.56 (m, 1 H)7.57 - 7.61 (m, 2 H) 7.79 (d, J=2.0 Hz, 1 H) 8.30 (d, J=4.9 Hz, 1 H) 11.86(br. s., 1 H). LCMS: m / z 467 [M+H] + HRMS (ESI) for C 21 H 16 Cl2F3N4O [M+H] + The calculated value is 467.0648, and the measured value is 467.0656. 2-(2,4-Dichlorophenyl)-1-methyl-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl), R2=2,4-dichlorophenyl, R3=R5=H, R4=methyl] Compound 56 1 H NMR (500 MHz, DMSO- d 6) δ ppm 3.30 (s, 1 H) 6.60 (dd, J =3.43, 1.91Hz, 1 H) 6.74 (br. s., 1 H) 7.02 (s, 1 H) 7.11 (d, J =4.88 Hz, 1 H) 7.38 (br.s., 1 H) 7.50 - 7.52 (m, 2 H) 7.56 (t, J =1.00 Hz, 1 H) 7.76 (s, 1 H) 8.27 (d, J =4.88 Hz, 1 H) 11.81 (br. s., 1 H). LCMS: m / z 385 [M+H] + HRMS (ESI) for C 19 H 14Cl2N4O [M+H] + The calculated value is 385.0618, and the measured value is 385.0616. 2-(2,4-Dichlorophenyl)-1-ethyl-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide [R1=1H-pyrrolo[2,3-b]pyridin-4-yl), R2=2,4-dichlorophenyl, R3=R5=H, R4=ethyl] Compound 57 1 H NMR (500 MHz, DMSO- d 6) δ ppm 0.73 (t, J =7.17 Hz, 3 H) 3.61 - 3.90(m, 2 H) 6.51 (dd, J =3.36, 1.83 Hz, 1 H) 6.72 (br. s., 1 H) 6.93 (s, 1 H)7.10 (d, J =4.88 Hz, 1 H) 7.32 (br. s., 1 H) 7.48 - 7.59 (m, 3 H) 7.75 (d, J =1.83 Hz, 1 H) 8.28 (d, J =5.03 Hz, 1 H) 11.83 (br. s., 1 H). LCMS: m / z 399 [M+H] + HRMS (ESI) for C 20 H 16 Cl2N4O [M+H] + The calculated value is 399.0774, and the measured value is 399.0767.

Claims

1. A compound of formula (I): in: R1 is a heteroaryl group selected from the group consisting of: , , , and in: Ra, Rb, and Rc are independently straight-chain or branched (C1-C6) alkyl groups, either hydrogen or optionally substituted with halogens. R2 is a substituted phenyl ring or a substituted α-naphthyl or β-naphthyl group, α-tetrahydronaphthyl or β-tetrahydronaphthyl group, having one to three substituents selected from the following: halogen, nitro, aminocarbonyl, straight-chain or branched (C1-C6) alkyl, straight-chain or branched (C1-C6) alkoxy, straight-chain or branched polyfluorinated (C1-C6) alkyl and straight-chain or branched polyfluorinated (C1-C6) alkoxy; The condition is that 2,5-disubstituted phenyl groups are excluded; R3 is hydrogen; a straight-chain or branched (C1-C4) alkyl group, optionally substituted with 1 to 3 groups independently selected from: (C1-C6) alkylamino, di(C1-C6) alkylamino, halogen, (C5-C6) heterocyclic group, in which one or two carbon atoms are replaced by a heteroatom selected from nitrogen or oxygen, and a 5-membered heteroaryl group having a heteroatom O; cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl groups optionally substituted with an amino group; or a (C5-C6) heterocyclic group having a heteroatom N optionally substituted with a (C1-C6) alkyl group; R4 is a straight-chain or branched (C1-C6) alkyl group, either hydrogen or optionally substituted with 1-3 groups independently selected from hydroxyl or halogen groups; and R5 is a hydrogen, halogen, or straight-chain or branched (C1-C3) alkyl group; Or its pharmaceutically acceptable salt.

2. The compound of formula (I) according to claim 1, or a pharmaceutically acceptable salt thereof, wherein: Ra, Rb, and Rc are independently straight-chain or branched (C1-C6) alkyl groups, either hydrogen-containing or optionally halogen-substituted; and R2 is a 2,4-disubstituted phenyl group.

3. The compound of formula (I) according to claim 2, or a pharmaceutically acceptable salt thereof, wherein: R2 is a 2,4-disubstituted phenyl group; R3 is a hydrogen-containing or straight-chain or branched (C1-C4) alkyl chain, optionally substituted with 1-3 independently selected groups from: (C1-C6) alkylamino, di(C1-C6) alkylamino, halogen, and (C5-C6) heterocyclic groups, wherein one or two carbon atoms are replaced by heteroatoms selected from nitrogen and oxygen; and R5 is hydrogen.

4. The compound of formula (I) according to claim 3, or a pharmaceutically acceptable salt thereof, wherein: R4 is hydrogen.

5. The compound of formula (I) according to claim 1, or a pharmaceutically acceptable salt thereof, selected from the group consisting of: 2-(3-chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 1); 2-(4-chloro-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 2); 2-(2-chloro-4-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 3); 2-(2,4-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 4); 2-[2-chloro-4-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 5); 2-(2,3-difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 6); 2-(2,3-dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 7); 2-[4-methyl-2-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 8); 2-(2-chloro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 9); 2-(2,3-difluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 10); 2-[2-methyl-4-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 11); 2-(2-fluoro-3-methoxyphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 12); 2-(2-chloro-3-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 13); 2-(2-fluoro-3-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 14); 2-[2-methyl-3-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 15); 2-[4-methoxy-2-(trifluoromethyl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 16); 2-[2-chloro-4-(difluoromethoxy)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 17); 2-(3,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 18); 2-(3,4-Difluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 19); 2-(3-ethoxy-2-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 20); 2-(4-methyl-3-nitrophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 21); 2-(3-carbamoyl-4-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 22); 2-(2-fluoro-4-methylphenyl)-N-[2-(pyrrolidine-1-yl)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 23); N-[2-(dimethylamino)ethyl]-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 24); 2-(2-fluoro-4-methylphenyl)-N-[2-(morpholin-4-yl)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 25); N-[(1S,2R)-2-aminocyclohexyl]-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 26); 2-(2-fluoro-4-methylphenyl)-N-(furan-2-ylmethyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 27); N-(fluoroethyl)-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 28); 2-(2-fluoro-4-methylphenyl)-N-[2-(methylamino)ethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 29); Compound 2-(2-fluoro-4-methylphenyl)-N-(1-methylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 30); 2-(4-methylnaphth-1-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 32); 2-(3-fluorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 33); 5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-2-[4-(trifluoromethoxy)phenyl]-1H-pyrrolo-3-carboxamide (compound 34); 2-(4-fluoro-2-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 37); 2-(2-fluoro-4-methylphenyl)-4-iodo-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 38); 4-Bromo-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 39); 4-Ethyl-2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (Compound 40); 2-(2-fluoro-4-methylphenyl)-4-(propyl-2-yl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 41); 5-(6-aminopyrimidin-4-yl)-2-(2,4-dichlorophenyl)-1H-pyrrole-3-carboxamide (Compound 42) 2-(2,4-Dichlorophenyl)-5-(1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide (compound 43); 2-(2,4-Dichlorophenyl)-5-(3-methyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide (compound 44); 5-(2-amino-1,3-thiazolyl-4-yl)-2-(2,4-dichlorophenyl)-1H-pyrrole-3-carboxamide (compound 45); 2-(2,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 46); 2-(2,4-Dichlorophenyl)-5-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 47); 2-(2,4-Dichlorophenyl)-5-[3-(trifluoromethyl)-1H-pyrazol-4-yl]-1H-pyrrole-3-carboxamide (compound 48); 2-(2-fluoro-4-methylphenyl)-5-(1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide (compound 49); 5-(3,5-dimethyl-1H-pyrazol-4-yl)-2-(2-fluoro-4-methylphenyl)-1H-pyrrole-3-carboxamide (compound 50); 2-(2-fluoro-4-methylphenyl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide (compound 51); 2-(2-fluoro-4-methylphenyl)-5-(3-methyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carboxamide (compound 52); 2-(2-fluoro-4-methylphenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 53); 2-(2,4-Dichlorophenyl)-1-(2-hydroxyethyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 54); 2-(2,4-Dichlorophenyl)-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-(3,3,3-trifluoropropyl)-1H-pyrrolo-3-carboxamide (Compound 55); 2-(2,4-dichlorophenyl)-1-methyl-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 56); and 2-(2,4-dichlorophenyl)-1-ethyl-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrrolo-3-carboxamide (compound 57).

6. A pharmaceutical composition comprising a compound of formula (I) as defined in any one of claims 1-5 or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable excipient, carrier or diluent.

7. The compound of formula (I) as defined in any one of claims 1-5, or a pharmaceutically acceptable salt thereof, for use as a medicine.

8. Use of a compound of formula (I) as defined in any one of claims 1-5, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for treating diseases caused by and / or related to dysregulated Cdc7 kinase activity.

9. Use of the compound according to claim 8, wherein the disease is selected from the group consisting of cancer and cell proliferation disorders.

10. Use of the compound according to claim 9, wherein the cancer is selected from the group consisting of: cancer, the cancer being selected from the group consisting of: bladder cancer, breast cancer, kidney cancer, liver cancer, colon cancer, lung cancer, esophageal cancer, gallbladder cancer, ovarian cancer, pancreatic cancer, gastric cancer, cervical cancer, prostate cancer, head and neck cancer, and skin cancer; lymphoid hematopoietic tumors, the lymphoid hematopoietic tumors being selected from the group consisting of: leukemia, acute lymphoblastic leukemia, acute lymphoblastic leukemia, B-cell lymphoma, angioimmunoblastic T-cell lymphoma, Hodgkin lymphoma, non-Hodgkin lymphoma, pilocellular lymphoma, mantle cell lymphoma, and Burkitt lymphoma; bone marrow hematopoietic tumors, wherein... The bone marrow hematopoietic tumors are selected from the following groups: acute and chronic myeloid leukemia, myelodysplastic syndromes, and promyelocytic leukemia; tumors of mesenchymal origin; tumors of the central and peripheral nervous systems, selected from the following groups: glioma, glioblastoma, glioblastoma multiforme, astrocytoma, oligodendroglioma, paraganglioma, neuroblastoma, and schwannoma; melanoma, seminoma, teratoma, osteosarcoma, xeroderma pigmentosum, keratoacanthoma; thyroid cancer selected from the group consisting of papillary thyroid carcinoma and medullary thyroid carcinoma; Kaposi's sarcoma, chondrosarcoma, cholangiocarcinoma, and head and neck tumors.

11. Use of the compound according to claim 9, wherein the cancer is selected from the group consisting of: small cell lung cancer, squamous cell carcinoma, fibrosarcoma, and rhabdomyosarcoma.

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