Carbamate compound

Description

1 / 79 CARBAMATE COMPOUND Technical Field

[001] The present invention relates to a carbamate compound. Previous Technique

[002] Carbamate compounds are known to be used in applications not only as intermediates in chemicals such as solvents, pharmaceuticals and pesticides, but also, for example, as raw materials for nylon. It has also been reported that carbamate compounds are used as titanium catalysts supported by Mg compounds, used in the polymerization of olefins.

[003] A catalyst for olefin polymerization is one of the techniques widely developed to date, driven by the discovery of the so-called Ziegler-Natta catalysts, for which Ziegler reported in 1953 that ethylene was polymerized even at low pressures using a combination of titanium tetrachloride and an organoaluminum compound, and Natta subsequently reported the first polymerization of propylene using a combination of titanium trichloride and a halogen-containing organoaluminum compound. Meanwhile, catalysts containing titanium tetrachloride, a magnesium compound, and a Lewis base, termed third-generation catalysts, were found to achieve high polymerization activity (high productivity) and high stereoregularity in propylene polymerization. This provided an opportunity for propylene polymers (polypropylene) to spread throughout the world.

[004] A Lewis base (hereinafter also referred to as an internal donor), one of the main components of the third-generation catalyst component mentioned above (hereinafter also referred to as a solid titanium catalyst component), has been shown to significantly affect the performance of Petition 870250087268, dated 09 / 26 / 2025, page 13 / 94 2 / 79 catalyst, and several Lewis bases have been developed to date.

[005] As Lewis bases for use in ZieglerNatta catalysts, ethyl benzoate, phthalic esters, 1,3-diketone (Patent Literature 1), malonic ester (Patent Literature 2), succinic ester (Patent Literature 3), 2,4-pentanediol diester (Patent Literature 4), naphthalenediol diester (Patent Literature 5), and catechol diester (Patent Literature 6) have been reported. Companies are conducting intensive research and development in this area to date. A carbamate compound with a specific structure has also been reported as suitable (Patent Literature 7 to 9). List of Citations

[006] Patent Literature Patent Literature 1: JP 2005-226076A Patent Literature 2: JP 2000-516987A Patent Literature 3: JP 2002-542347A Patent Literature 4: JP 2005-517746A Patent Literature 5: JP 2011-529888A Patent Literature 6: JP 2014-500390A Patent Literature 7: WO2016 / 184884 Patent Literature 8: US Patent No. 10005859 Patent Literature 9: US Patent No. 10836847 Summary of the Invention Technical Problem

[007] Propylene polymers, although having heat resistance and stiffness similar to those of general-purpose engineering plastics, have the advantage of generating a smaller amount of toxic gas, even when treated by combustion, because they are substantially composed only of carbon and hydrogen.

[008] With recent advances in molding techniques, the use of a propylene polymer with greater stereoregularity than before has the potential to develop properties Petition 870250087268, dated 09 / 26 / 2025, page 14 / 94 3 / 79 superior physical properties (such as stiffness and heat resistance). For this reason, the market has demanded propylene polymers with greater stereoregularity. From the point of view of resource economy and environmental protection, methods for producing a propylene polymer with high productivity have also been necessary.

[009] Therefore, the objective of the present invention is to provide a suitable internal donor component for a solid titanium catalyst component, capable of producing a propylene polymer with extremely high stereoregularity and high productivity (high activity), when used primarily for solid titanium catalyst components. Solution to the Problem

[010] As a result of a diligent study to solve the above problems, the present inventors discovered that a carbamate compound with a specific structure is suitable as, for example, a Lewis base for a solid titanium catalyst component, and concluded the present invention. Examples of the present invention will be shown below.

[011] {1} A carbamate compound represented by the following formula (0): {Chemistry 1} (0) where it is 0 or 1, Petition 870250087268, dated 09 / 26 / 2025, page 15 / 94 m is an integer from 1 to 4, n is an integer from 1 to 4, R1 and R2 are each substituents with an R10CR2- structure. R3 is a hydrogen atom or a substituent with an R10-CR2- structure. R4 is a substituent selected from among a substituent with an R10-CR2- structure, a substituent with an R10At16- structure, and a substituent with an R102-At15- structure. At15 is an atom from Group 15 in the periodic table, and At16 is an atom from Group 16 in the periodic table. R and R10 are each a group containing one atom selected from carbon, hydrogen, and elements from Groups 15, 16, and 17 of the periodic table, which have from 0 to 17 carbon atoms and from 0 to 4 atoms of the elements in Groups 15, 16, and 17 of the periodic table. R1a, R4e, and R can link to form a monocyclic or polycyclic ring, and a plurality of R and R10 can link to form a monocyclic or polycyclic ring or form a multiple bond.

[012] {2} The carbamate compound according to {1}, wherein the compound is represented by the following formula (1): {Chemistry 2} (D where n is an integer from 2 to 4, in R1, R2, R3, R4 and Petition 870250087268, dated 09 / 26 / 2025, page 16 / 94 5 / 79 R have the same meaning as m, R1, R2, R3, R4, and R in formula (0) .

[013] {3} The carbamate compound according to {1} or {2}, where R3 is a substituent with an R10-CR2- structure.

[014] {4} The carbamate compound according to any one of {1} to {3}, where R4 is a substituent with a structure R10CR2- .

[015] {5} The carbamate compound according to any one of {1} to {4}, where At15 is a nitrogen atom.

[016] {6} The carbamate compound according to any one of {1} to {5}, where At16 is an oxygen atom. Advantageous Effects of the Invention

[017] The carbamate compound of the present invention can be used, for example, as a drug, such as an insecticide, or an intermediate thereof, as a feedstock for an optical resolution column, or as a feedstock for a Ziegler-Natta catalyst. Description of the Modalities Carbamate compound

[018] A carbamate compound of the present invention is represented by the following formula (0). {Chemistry 3} Petition 870250087268, dated 09 / 26 / 2025, page 17 / 94 6 / 79 where l is 0 or 1, m is an integer from 1 to 4, n is an integer from 1 to 4, R1 and R2 are each substituents with an R10CR2- structure. R3 is a hydrogen atom or a substituent with an R10-CR2- structure. R4 is a substituent selected from among a substituent with an R10-CR2- structure, a substituent with an R10At16- structure, and a substituent with an R102-At15- structure. At15 is an atom from Group 15 in the periodic table, and At16 is an atom from Group 16 in the periodic table. R and R10 are each a group containing an atom selected from carbon, hydrogen elements, and Groups 15, 16, and 17 of the periodic table, which have from 0 to 17 carbon atoms and from 0 to 4 heteroatoms. R1a, R4e, and R can link to form a monocyclic or polycyclic ring, and a plurality of R and R10 can link to form a monocyclic or polycyclic ring or form a multiple bond.

[019] One of the preferred aspects of the structural formula is a compound specified by the following formula (1). In this case, n is an integer from 2 to 4. Other symbols have the same meaning as those in formula (0). Petition 870250087268, dated 09 / 26 / 2025, page 18 / 94 7 / 79 {Chemistry 4}

[020] 0 At15, which is an atom of Group 15 in the periodic table, is preferably an atom selected from, for example, nitrogen, phosphorus, arsenic and antimony, more preferably an atom selected from nitrogen and phosphorus, and particularly preferably an atom of nitrogen.

[021] At16, which is an atom of Group 16 in the periodic table, is preferably an atom selected from, for example, oxygen, sulfur and selenium, more preferably an atom selected from oxygen and sulfur, and particularly preferably an oxygen atom.

[022] The symbol represents a covalent bond, and the term atom can refer to the atom itself, or to a structure with a covalent bond in a compound or a substituent. For example, in the case of an oxygen atom, the expression -O- is referred to as an oxygen atom in some cases.

[023] R and R10 are each a group containing an atom selected from carbon, hydrogen, and elements of Groups 15, 16, and 17 of the periodic table, which have from 0 to 17 carbon atoms and from 0 to 4 atoms of elements from Groups 15, 16, and 17 of the periodic table. Elements of Groups 15 and 16 may be elements such as those exemplified in At15 and At16. Preferred examples of elements of Group 17 may include fluorine, chlorine, bromine, and iodine, and more preferably an atom selected from Petition 870250087268, dated 09 / 26 / 2025, page 19 / 94 8 / 79 Fluorine, chlorine and bromine, even more preferably an atom selected from among fluorine and chlorine is even more preferable, and particularly chlorine.

[024] The lower limit value of the number of carbon atoms is preferably one, and the upper limit value of the same is preferably 15, more preferably 13, even more preferably 11, and particularly preferably 9.

[025] The upper limit value of the number of atoms of elements in Groups 15, 16 and 17 in the periodic table is preferably 3 and more preferably 2.

[026] These substituents (R1, R2, R3, R4, R10 and R) are capable of linking together to form, for example, a cyclic structure, a polycyclic structure, or an aromatic structure. In the present invention, unless specifically described otherwise, a double bond or a triple bond is considered as a two-membered ring and a type of cyclic structure.

[027] The plurality of R and R10 can link together to form, for example, a cyclic structure, a polycyclic structure or an aromatic structure. When carbon atoms adjacent to which these substituents are attached form a double bond, these R and R10 can be considered as being directly linked to each other to form the double bond.

[028] A plurality of R and R10 may be present, and they may have the same structure or a different structure. Specific examples of such substituents include substituted or unsubstituted hydrocarbon groups with 1 to 17 carbon atoms. Examples of such substituents may include aliphatic substituents, alicyclic substituents, and hydrocarbon groups with an aryl group and 6 to 20 carbon atoms. These may be a structure containing any of the atoms from Groups 15 to 17 in the periodic table (in the present invention, referred to as a Petition 870250087268, dated 09 / 26 / 2025, p. 20 / 94 9 / 79 heteroatom in some cases), as described above. These are preferably a hydrocarbon group consisting of carbon and hydrogen.

[029] Preferred examples of the hydrocarbon group may include a monovalent hydrocarbon group with 0 to 15 carbon atoms, preferably 0 to 13 carbon atoms, more preferably 1 to 11 carbon atoms, and even more preferably 1 to 9 carbon atoms. In the present invention, when the number of carbon atoms is zero, it refers to a hydrogen atom or a covalent bond forming a double bond.

[030] Specific examples of such hydrocarbon groups include aliphatic hydrocarbon groups, alicyclic hydrocarbon groups and aromatic hydrocarbon groups, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a decyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group, an eicosyl group, a cyclohexyl group, a substituted or unsubstituted aryl group, such as a phenyl group, and a substituted or unsubstituted cycloalkenyl group. Among these, for example, an n-butyl group, an isobutyl group, a hexyl group, an octyl group, and a phenyl group are preferred, and an n-butyl group, an isobutyl group, and a phenyl group are most preferred.

[031] The hydrocarbon group may be a hydrocarbon group containing a heteroatom, such as nitrogen, oxygen, phosphorus, or a halogen, as described above. Such a heteroatom is particularly oxygen or nitrogen. Such substituents may be selected from known structures. More specific preferred examples may include a group containing a carbonyl structure, such as a carboxylic acid ester group, an aldehyde group, an acetyl group, or an oxycarbonylalkyl group, Petition 870250087268, dated 09 / 26 / 2025, p. 21 / 94 10 / 79 an alkoxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyloxy group, a substituted or unsubstituted cycloalkyloxy group, a substituted or unsubstituted cycloalkenyloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, and a siloxy group.

[032] R1 and R2 are each substituents with an R10-CR2- structure. Examples of such substituents are substantially almost the same as the substituents exemplified as R and R10, but a portion that binds to the nitrogen of a carbamate group described below is limited to the carbon. For example, structures that bind to other groups via oxygen or nitrogen, such as an alkoxy group and an amino group, are excluded from such substituents. Specific preferred examples of such substituents include an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a hexyl group, an octyl group, and a phenyl group, and more preferably an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a phenyl group, and particularly preferably an ethyl group, a propyl group, an isopropyl group, and a phenyl group.

[033] R3 is the definition of R1 or R2 to which a hydrogen atom has been added. R3 is preferably a substituent with an R10-CR2- structure. Therefore, specific examples of preferred substituents are also the same as those of R1 and R2.

[034] R4 is a substituent selected from a substituent with the structure R10-CR2-, a substituent with the structure R10-At16-, and a substituent with the structure R102-At15. Specific examples of this R4 are practically the same as the substituents exemplified as R, R10, R1, and R2. At16 is preferentially oxygen, and the preferred example of At15 is Petition 870250087268, dated 09 / 26 / 2025, page 22 / 94 11 / 79 nitrogen. Specific examples of the R10-At16- structure may include an alkoxy group and an aryloxy group, and more specific preferred examples of the substituents may include an ethoxy group, a propoxy group, a butoxy group, an acetyloxy group, an ethylcarbonyloxy group, a metalloyloxy group, a phenoxy group, and a substituted phenoxy group.

[035] Specific examples of the R10-At15- structure may include a dimethylamino group, a diethylamino group, a dipropylamino group, a diisopropylamino group, a dibutylamino group, a methylethylamino group, a methylpropylamino group, a diphenylamino group and a ditolylamino group.

[036] The carbamate compound of the present invention is a structure having a substituent of a carbamate structure and a substituent of an amide structure, as shown in formula (1). In particular, the substituent with a carbamate structure is linked to A through the oxygen (O-), and the substituent of an amide structure is linked to A through the nitrogen (N-). In the present invention, the carbamate group and an amide group are simply referred to as a functional group in some cases. The amide group may become a substituent with a different name, such as a carbamate group, due to the structure of R4.

[037] The carbamate compound specified by formula (0) of the present invention is a structure having a carbamate structure substituent and an amide structure substituent on a divalent group of such structure as formula (0') shown below. The carbamate compound specified by formula (1) of the present invention is a structure having a carbamate structure substituent and an amide structure substituent on a divalent group of such structure as formula (1') shown below. Petition 870250087268, dated 09 / 26 / 2025, p. 23 / 94 12 / 79 {Chemistry 5}

[038] The symbols, such as C and R in formula (O') and in formula (1') have the same meanings as the symbols in formula (0) and in formula (1).

[039] Q 1 in formulas (0) and (O') are 0 or 1 and preferably 1.

[040] The molecular skeleton corresponds to formula (1) in the case where 1 in formula (0) is 1 and corresponds to formula (1') in the case where 1 in formula (0') is 1.

[041] m is an integer from 1 to 4. In the case of formula (0) , the value of m is preferably 1 or 2 and most preferably 1. In the case of formula (1), a preferred lower bound value of m is 2, and a preferred upper bound value is 3.

[042] n is an integer from 1 to 4. In the case of formula (0), the value of n is preferably 1 or 2 and most preferably 1. In formula (1), an aspect in which the value Petition 870250087268, dated 09 / 26 / 2025, p. 24 / 94 13 / 79 of n is from 1 to 4 is also within the scope of the present invention, but the value of n is preferably from 2 to 4, more preferably 2 or 3, and even more preferably 2.

[043] The sum of men is from 2 to 8, preferably from 2 to 7, more preferably from 2 to 6, and particularly preferably from 2 to 5 in the case of formula (0).

[044] The sum of men is from 3 to 8, preferably from 3 to 7, more preferably from 3 to 6, and particularly preferably from 3 to 5 in the case of formula (1).

[045] In the case of l = 0 in formula (0), R1, R2 and R4 are preferably substituents with 2 or more carbon atoms. In particular, R1, R2 and R4 are preferably hydrocarbon groups consisting of carbon and hydrogen, and more specifically, aliphatic hydrocarbon groups with 2 to 10 carbon atoms, branched aliphatic hydrocarbon groups, and aromatic hydrocarbon groups are preferred.

[046] Among them, R1 and R2 are preferably aliphatic hydrocarbon groups with 2 to 10 carbon atoms, branched aliphatic hydrocarbon groups and alicyclic hydrocarbon groups, and the number of carbon atoms is more preferably from 2 to 6, even more preferably from 2 to 4, and particularly preferably 2 or 3. Specific preferred examples of substituents may include an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a 2-butyl group, a pentyl group, a hexyl group, an octyl group and a decyl group, and more preferably an ethyl group, a propyl group, a butyl group and a hexyl group, even more preferably an ethyl group and a butyl group, and particularly an ethyl group.

[047] R4 is more preferably an aromatic hydrocarbon group, even more preferably a phenyl group or a substituted phenyl group, and particularly preferably a Petition 870250087268, dated 09 / 26 / 2025, page 25 / 94 14 / 79 phenyl group.

[048] Cyclic structures such as formula (0') and formula (1') can be alicyclic structures or aromatic structures. In the case of the alicyclic structure, it is considered that relatively diverse conformations can be formed, therefore it is possible to expect that various active species, such as those described below, will be formed. On the other hand, the aromatic structure can be considered as a rigid structure in which electron transfer will likely occur, therefore it is possible to expect that a negative electron uniformity effect, as described below, will become significant.

[049] When the alicyclic structure is a structure that includes a double bond, it appears that R has disappeared at first glance, but it can be considered that the bonding of R to adjacent carbon atoms is directly linked to each other to form a double bond (which can also be considered as a two-membered ring), and the alicyclic structure is therefore a structure within the scope of the present invention. As the aromatic structure has this double bond formed in a specific position, the aromatic structure also falls within the scope of the present invention.

[050] The carbamate compound of the present invention can be suitably used as an internal donor compound (Lewis base) of a solid titanium catalyst component, as described above. The solid titanium catalyst component containing the carbamate compound with this specific structure tends to exhibit an excellent balance between, for example, activity, stereospecificity, molecular weight controllability, and reaction control. The reason for the solid titanium catalyst component having such an effect is not clear at present, but the present inventors presume, as described below. Petition 870250087268, dated 09 / 26 / 2025, page 26 / 94 15 / 79

[051] As described above, in the functional groups described above linked to A, the atoms directly bonded to A are different elements, nitrogen and oxygen, and it is possible to consider the possibility that the carbamate compound is electronically unbalanced and has a structure with active electron movement due to the uneven distribution of the electron cloud. Furthermore, both functional groups are groups that have structures in which two or more heteroatoms are contained, and, moreover, these heteroatoms are linked through a carbon atom. Also from this point of view, the structure can be considered as one in which an uneven distribution of the electron cloud can occur. That is, the structure is considered active in the movement of electrons in a double or triple direction. In addition, the molecular structure also allows for an asymmetric structure, which is expected to enable the formation of more varied active species.As described above, the unequal electronic distribution can become more significant in a case where the structure of formula (1') is an aromatic structure.

[052] On the other hand, in a case where the structure of formula (1') is an alicyclic structure, several active species attributed to confrontations are expected to be formed.

[053] The ability to form such a variety of active species is expected to produce a polymer with a wide molecular weight distribution. Furthermore, the uneven electronic distribution is expected to activate the appropriate electron donation to the titanium composite component, which will be described later. This is likely one of the reasons for the higher polymerization activity. In addition, this high activity also allows the formation of active species whose molecular weight can be increased and, therefore, as will be described later, the use of the solid titanium catalyst component of the present invention can be considered to provide Petition 870250087268, dated 09 / 26 / 2025, page 27 / 94 16 / 79 is easily an olefinic polymer with a molecular weight distribution that extends to the high molecular weight side.

[054] However, if many different active species are formed, it may be easier to use active species with low activity and stereospecificity. For this reason, it may be preferable that the substituent A in formula (1') has a rigid structure to some extent. [ 055]Examples of such carbamate compounds include the following structures. Some structural formulas of the following exemplary compounds have stereoisomers, and even isomeric structures are clearly represented for some exemplary compounds, but there may be isomeric structures that are not exemplified. {Chemistry 6} D-21 D-22 0-23 D-24 Petition 870250087268, dated 09 / 26 / 2025, p. 28 / 94 17 / 79 D-25 D-26 D-27 D-28 0 Me D-29 D-31 0 NMe2 D-35 D-36 D-37 D-38 D-44 D-45 0 D-46 {Chemistry 7} D-48 D-50 D-52 D-54 Et2N^.ON^Ph Π μ / il oo D-55 Et2N. .Ο N. .Ph Et2N. .0 N. .Ph Et2N. .0 N. .Ph Ϊ Me ϊ Ύ MeZϊ Y MeZY oooooo D-61 D-57 D-58 D-59 Petition 870250087268, of 26 / 09 / 2025, p. 29 / 94 18 / 79 Et2Nx,0 N_Me T Me7If 0 0 D-82 D-83 D-85 D-86 {Chemistry 8} oo E-1 E-6 E-7 E-8 E-9 E-10 00 OO OO 00 E-11 E-12 E-13 E-14 E-15 Petition 870250087268, dated 09 / 26 / 2025, page 30 / 94 19 / 79 E-16 E-17 E-18 E-19 E-20 E-21 E-23 E-24 E-25 E-31 E-32 E-33 E-34 {Chemistry 9} E-35 E-36 E-37 E-38 Petition 870250087268, dated 09 / 26 / 2025, page 31 / 94 20 / 79 Et2N .ON,_,NEt2Et2N O N.,,NEt2 Y μ / ϊ Y m / y 0 o E-64 E-65 E-67 E-68 {Chemistry 10} F-11 F-12 F-13 F-14 F-15 Petition 870250087268, dated 09 / 26 / 2025, page 32 / 94 21 / 79 And The Bu OPh F-26 F-31 OO Et2N Et2Nx.ON^OEt Et2N flπΒι / if 0 N OEt F-34 {Chemistry 11} F-38 F-39 Petition 870250087268, dated 09 / 26 / 2025, page 33 / 94 22 / 79 Et2N OEt Et2N {Chemistry 12} oo oo oo oo oo Q-166 Q-167 Q-168 Q-169 Q-170 {Chemistry 13} {Chemistry 14} Petition 870250087268, dated 09 / 26 / 2025, page 34 / 94 23 / 79 A-1 ο Ο ^-N / =( Ph Vo HN^( 0 0 A-6 The The A-4 The The A-5 A-11 A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-19 A-20 A-23 A-24 A-25 A-28 A-29 A-30 A-31 A-32 A-33 Et Me A-35 A-34 {Chemistry 15} the. Et2N / =( / Bu HN— / OO A-36 Et2N )=\ Bi HN— / OO A-37 A-38 A-39 A-40 A-46 A-47 A-48 A-49 A-50 Petition 870250087268, de 26 / 09 / 2025, pág. 35 / 94 24 / 79 A-51 A-52 A-53 A-54 A-55 A-61 A-62 A-63 A-64 A-65 Me dEt2N. / \zph Me O A-70 A-66 A-67 A-68 A-69 {Chemistry 16} Me A-71 A-72 A-73 Me Me A-74 Me Me A-75 A-76 A-77 A-78 A-79 A-80 A-81 A-82 A-83 A-84 A-85 A-86 A-87 A-88 A-89 A-90 Petition 870250087268, dated 09 / 26 / 2025, page 36 / 94 25 / 79 A-91 A-92 A-93 A-94 A-95 A-96 A-97 A-98 {Chemistry 17} B-1 B-3 B-4 B-5 B-12 B-13 B-14 B-15 OO OO 00 OO O B-16 B-17 B-18 B-19 B-20 B-21 B-22 B-23 B-24 B-25 {Chemistry 18} B-26 B-27 B-28 B-29 B-30 B-31 B-32 B-33 B-34 B-35 B-36 B-37 B-38 B-39 B-40 Petition 870250087268, dated 09 / 26 / 2025, page 37 / 94 26 / 79 B-41 B-42 B-43 B-44 B-45 Me B-46 B-49 Me Me B-50 {Chemistry 19} B-51 B-52 B-53 B-54 B-55 B-56 B-57 B-58 B-59 B-60 B-61 B-62 B-63 B-64 B-65 B-66 B-67 B-68 B-69 B-70 B-71 B-72 B-73 B-74 Petition 870250087268, dated 09 / 26 / 2025, page 38 / 94 27 / 79 {Chemistry 20} C-9 C-10 C-11 C-12 C-13 C-14 C-15 C-16 C-17 C-18 C-19 C-20 Ο ο “D o )=\ OEt N )=\ OEt Me OO Me O C-23 C-24 C-28 C-29 {Chemistry 21} Et O C-31 C-32 C-33 C-34 C-35 Me C-36 Me- Et2N )=( OEt Me O C-38 C-39 Me Me C-40 C-41 C-42 C-43 C-44 C-45 C-46 C-47 C-48 C-49 C-50 Petition 870250087268, dated 09 / 26 / 2025, page 39 / 94 28 / 79 C-55 C-60

[056] In structural formulas, the methyl group is indicated by Me, the ethyl group is indicated by Et, the propyl group is indicated by Pr, the butyl group is indicated by Bu, the phenyl group is indicated by Ph, the benzyl group is indicated by Bn, the cyclohexyl group is indicated by Cy, and the trifluoromethyl group is indicated by CF3. n represents normal, i represents iso, and et represents tertiary.

[057] A carbon atom is present at the intersection or terminal portion of the line in the structure. This method for expressing composite structures is a well-known method among those skilled in the art. Method for producing carbamate compound

[058] A method for producing a carbamate compound of the present invention is not particularly limited, and it is possible to use, for example, synthesis examples in the Examples described below. The carbamate compound can also be produced using a known reaction. The carbamate compound can also be synthesized by synthesizing each moiety by a known synthesis method and combining them by a known method. More specifically, it is possible to exemplify a method in which the carbamate compound is synthesized by the synthesis of an amide alcohol, as described below. In the following formulas, R' refers to a substituent that is linked by one atom. Petition 870250087268, dated 09 / 26 / 2025, p. 40 / 94 29 / 79 adjacent and a carbon atom. Method for synthesizing the N-amide portion

[059] In the following reaction formula (2), an amide compound can be synthesized, for example, by a reaction between an amino alcohol compound and 1 equivalent of an acid chloride in the presence of a base. Amino alcohol hydrochloride can be used in place of the amino alcohol. Examples of the base used may include, but are not limited to, sodium hydroxide, potassium hydroxide, pyridine, N,N-dimethyl-4-aminopyridine and triethylamine. {Chemistry 22}

[061] Alternatively, the amide compound corresponding to reaction formula (2) can be synthesized by synthesizing an N-amide / O-ester compound via a reaction between an amino alcohol compound and 2 or more equivalents of an acid chloride in the presence of a base and subsequently reacting the N-amide / O-ester compound with the base, as shown in reaction formula (3) below. The amino alcohol used in the synthesis of the N-amide / O-ester compound can be a corresponding hydrochloride, and examples of the base used may include, but are not limited to, sodium hydroxide, potassium hydroxide, pyridine, N,N-dimethyl-1,4-aminopyridine, and triethylamine. Examples of a method for synthesizing the N-amide / O-ester compound include the method involving the reaction of an amino alcohol compound with a carboxylic acid in the presence of an acid catalyst or the method using a condensation reagent such as N,N'-dicyclohexylcarbodiimide (DCC) (see reaction formula (4) below).Examples of bases that can be used in the synthesis of amide compounds include, but are not limited to, inorganic bases such as sodium hydroxide and potassium hydroxide, and organic bases such as... Petition 870250087268, dated 09 / 26 / 2025, page 41 / 94 30 / 79 piperidine and pyrrolidine. {Chemistry 23} >20 0 0 (3) {Chemistry 24} Catalyst Method for synthesizing the N-carbamate portion

[062] An N-carbamate compound shown in the following reaction formula (5) can be synthesized, for example, by a reaction between an amino alcohol compound and 1 equivalent of a chloroformate in the presence of a base. The amino alcohol used can be a corresponding hydrochloride. Examples of the base may include, but are not limited to, pyridine, N,N-dimethyl-4-aminopyridine and triethylamine. {Chemistry 25}

[063] Alternatively, the N-carbamate compound corresponding to reaction formula (5) can be synthesized by synthesizing an N-carbamate / O-carbonate compound by a reaction between an amino alcohol compound and 2 or more equivalents of a chloroformate in the presence of a base and subsequently reacting the N-carbamate / O-carbonate compound with the base, as shown in the following reaction formula (6). The amino alcohol used in the synthesis of the N-carbamate / O-carbonate compound can be a corresponding hydrochloride, and examples of the base used may include, but are not limited to, pyridine, N,N-dimethyl Petition 870250087268, dated 09 / 26 / 2025, page 42 / 94 31 / 79 aminopyridine and triethylamine. Examples of bases that can be used in the synthesis of the N-carbamate compound include, but are not limited to, inorganic bases such as sodium hydroxide and potassium hydroxide, and organic bases such as piperidine and pyrrolidine. {Chemistry 26} Method for synthesizing the diaminocarbonyl moiety

[064] A diaminocarbonyl compound shown in formula (7) below may be synthesized, for example, by a reaction between an amino alcohol compound and 1 equivalent of carbamoyl chloride in the presence of a base. The amino alcohol used may be a corresponding hydrochloride. Examples of the base may include, but are not limited to, sodium hydroxide, potassium hydroxide, pyridine, N,N-dimethyl-4-aminopyridine and triethylamine. {Chemistry 27} 1O (7)

[065] Alternatively, a diaminocarbonyl compound shown in reaction formula (7) below can also be synthesized by a reaction between an amino alcohol compound and 1 equivalent of an imidazolium salt in the presence of a base, as shown in reaction formula (8) below. The amino alcohol used can be a corresponding hydrochloride. Examples of the base may include, but are not limited to, pyridine, N,N-dimethyl-4-aminopyridine, triethylamine and n-butyllithium. Petition 870250087268, dated 09 / 26 / 2025, page 43 / 94 32 / 79 {Chemistry 28} 1eq U(8) Method for synthesizing the O-carbamate portion

[066] A compound shown in the following reaction formula (9) can be synthesized, for example, by a reaction between one of the phenols described above and a chloroformate in the presence of a base. Examples of the base may include, but are not limited to, pyridine, N,N-dimethyl-4-aminopyridine and triethylamine. {Chemistry 29} OOO (9) Method for synthesizing the N-alkyl portion

[067] A compound shown in the following reaction formula (10) can be synthesized, for example, by a reaction between the compound described above and a base and a subsequent reaction with an alkyl halide. Examples of the base may include, but are not limited to, organolithium reagents and sodium hydride. {Chemistry 30}

[068] These compounds can be used in various applications described below. In this case, one of these compounds can be used alone, or two or more of them can be used in combination. These carbamate compounds can also be used in conjunction with other compounds, provided that the objective of the present invention is not compromised. For example, in the case of being used as an internal donor of a solid titanium catalytic component, the compound of Petition 870250087268, dated 09 / 26 / 2025, page 44 / 94 33 / 79 carbamate can be used in combination with one of the alcohols described below or with a known electron donor, such as an ester or an ether.

[069] When used as a component of solid titanium catalyst, the carbamate compound can be formed in the process of preparing the solid titanium catalyst component.

[070] As applications of the carbamate compound of the present invention, it is expected that it will be used not only as an internal donor component of a solid titanium catalyst component used as a polymerization catalyst for olefins, but also in pharmaceuticals, such as not only pesticides, but also as intermediates or raw materials for pharmaceuticals and pesticides. As the carbamate compound is expected to be a structure with unique polarity, it is also expected that the carbamate compound will be suitable as a raw material for a column packing, for example, for an optical isomer separation column (a chiral separation column). The carbamate compound may also possibly be considered as a raw material for a polycondensation product, such as nylon. EXAMPLES Method for analyzing compounds

[071] A 1H-NMR spectrum (400 MHz, manufactured by JEOL Ltd., measuring instrument type JNM-ECZ400S / L1) was measured, and the peaks were assigned by a routine method to determine the structure. Example 1 Synthesis of compound 1

[072] Compound 1 shown below was synthesized by a method described below, according to the following reaction formula. Petition 870250087268, dated 09 / 26 / 2025, p. 45 / 94 34 / 79 {Chemistry 31} K2CO3 MeOH

[073] 2.93 g of 8-amino-1-naphthol hydrochloride (15.0 mmol eq) and 60 mL of chloroform (dehydrated) were added to a 300 mL three-necked flask, dried in an oven, containing a magnetic stirring bar in a nitrogen atmosphere. Then, 6.04 mL of pyridine (dehydrated) (75.0 mmol eq) were added slowly dropwise at room temperature. After cooling the reaction solution in an ice bath, 3.87 mL of benzoyl chloride (33.0 mmol eq) was added. 2.2 eq) were added slowly dropwise. After the dropwise addition was complete, the reaction solution was heated to room temperature and stirred for five hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 15 mL of methanol were added, and the reaction solution was stirred at room temperature for 30 minutes. Water, dichloromethane, and methanol were added to the reaction solution, and extraction was then performed three times with dichloromethane. A combined organic layer was dried over sodium sulfate and concentrated in a rotary evaporator. 8.81 g of the crude product obtained were purified by silica gel column chromatography (eluent: hexane:dichloromethane = gradient from 50:50 to 0:100) to obtain 3.60 g of intermediate 1'. 3.60 g of intermediate 1', 70 mL of Petition 870250087268, dated 09 / 26 / 2025, page 46 / 94 35 / 79 methanol and 1.76 g of potassium carbonate (12.7 mmol) were added to a 500 mL round-bottom flask, and the solution was stirred at 40 °C for two hours. After the reaction was complete, water and dichloromethane were added, and extraction was performed three times with dichloromethane. Furthermore, the aqueous layer was acidified by the addition of ammonium chloride, and extraction was then performed again three times with dichloromethane. The combined organic layer was dried over sodium sulfate and then concentrated in a rotary evaporator. The organic layer was suspended with hexane, filtered, and purified to obtain 2.53 g of compound 1 (9.61 mmol, 64% yield). Synthesis of compound 2

[074] Compound 2 shown below was synthesized by a method described below. {Chemistry 33} (Compound 2)

[075] 27.5 g of compound 1 (104.4 mmol, 1 eq) and 349 mL of pyridine were added to a 1 L three-necked flask, dried in an oven containing a magnetic stirring bar in a nitrogen atmosphere, and stirred at room temperature. 33.1 mL of diethylcarbamoyl chloride (261.1 mmol, 2.5 eq) were added slowly dropwise. After the dropwise addition, the reaction solution was refluxed for one hour. After the reaction was complete, the reaction solution was cooled to room temperature. Then, the reaction solution was added to 800 mL of ice-cold distilled water. Extraction was performed twice with diethyl ether, and a combined organic layer was washed once with 1 N hydrochloric acid and once with 1 N hydrochloric acid. Petition 870250087268, dated 09 / 26 / 2025, page 47 / 94 36 / 79 saturated aqueous solution of sodium bicarbonate, and dried over anhydrous magnesium sulfate. The organic layer was concentrated in a rotary evaporator to obtain 23.8 g of the crude product. As a result of the purification of the crude product obtained by silica gel column chromatography (eluent: hexane: ethyl acetate = gradient from 4:1 to 2:1), 15.1 g of compound 2 were obtained (41.7 mmoles, 40% yield). Preparation of the solid titanium catalytic component {α1}

[076] After sufficient nitrogen replacement in a 1-liter glass container, 85.8 g of anhydrous magnesium chloride, 321 g of decane, and 352 g of 2-ethylhexyl alcohol were added and heated and reacted at 130 °C for three hours to produce a homogeneous solution. 241 g of this solution and 6.43 g of ethyl benzoate were added to a glass container and stirred and mixed at 50 °C for one hour.

[077] After cooling the homogeneous solution thus obtained to room temperature, 38.3 ml of this homogeneous solution were added dropwise to 100 ml of titanium tetrachloride, which was kept at -20 °C for 45 minutes under stirring. After the loading was complete, the temperature of this mixed liquid was raised to 80 °C for 3.8 hours, and when the temperature reached 80 °C, 1.83 g of compound 2 was added to the mixed liquid. The temperature was raised again to 120 °C for 40 minutes, and the mixture was kept at the same temperature for 35 minutes under stirring. After the reaction was complete, a solid portion was recovered by hot filtration; this solid portion was again suspended in 100 ml of titanium tetrachloride, and a heating reaction was carried out again at 120 °C for 35 minutes, under stirring of the solid portion.After the reaction was complete, the solid portion was recovered again by hot filtration and thoroughly washed with decane at 100 °C and decane at room temperature until no free titanium compounds were detected in the washing liquid. A component of... Petition 870250087268, dated 09 / 26 / 2025, page 48 / 94 37 / 79 Solid titanium catalyst {α1} prepared by the operation described above was preserved as a decane paste, and a portion of this paste was dried to verify the catalyst composition. The composition of the solid titanium catalyst component {α1} thus obtained contained 0.42% by mass of titanium, 1.4% by mass of magnesium, and 0.11% by mass of a 2-ethylhexyl alcohol residue. Polymerization

[078] After adding 500 g of propylene and 1 NL of hydrogen at room temperature to a polymerization vessel with an internal capacity of 2 L, a mixture obtained by mixing 7 mL of heptane, 0.5 mmol of triethyl aluminum, 0.1 mmol of cyclohexylmethyldimethoxysilane and 0.004 mmol of the solid titanium catalyst component {α1} (in terms of titanium atoms) at 25 °C for 10 minutes was added, and the temperature inside the polymerization vessel was rapidly raised to 70 °C under stirring. After polymerization at 70 °C for 1.5 hours, the reaction was stopped with a small amount of ethanol and the propylene was purged. In addition, the polymer particles obtained were dried under reduced pressure at 80 °C overnight. For example, activity, apparent specific gravity, MFR, the amount of a decane-insoluble fraction, Tm, Tmf, and MWD are described below.

[079] Activity: 34.1 kg-PP / g-catalyst.

[080] Bulk specific gravity: 470 kg / m3.

[081] MFR: 1.1 g / 10 minutes.

[082] Content of insoluble decane: 1.72% by mass.

[083] Tm: 163.7 °C, 148.2 °C.

[084] Tc: 117.1 °C.

[085] Tmf: 172.4 °C.

[086] ΔH: 91.1 J / g.

[087] Mw / Mn: 11.22.

[088] Mz / Mw: 5.45. Petition 870250087268, dated 09 / 26 / 2025, page 49 / 94 38 / 79

[089] The methods for measuring the physical properties described above are as follows.

[090] (1) Bulk specific gravity: Bulk specific gravity was measured in accordance with JIS K-6721 standard.

[091] (2)Melting flow rate (MFR): According to ASTM D1238E, the measurement temperature for a propylene polymer was set to 230 °C with a load of 2.16 kg.

[092] (3)Quantity of soluble (insoluble) part in decane: A glass measuring container is loaded with approximately 3 grams of propylene polymer (measured with an accuracy of 10-4 g; the weight is indicated by b (gram) in the following formula), 500 ml of decane, and a small amount of a heat-resistant stabilizer soluble in decane, and the propylene polymer was dissolved by heating at 150 °C for two hours, under stirring with a stirrer in a nitrogen atmosphere, remaining at rest at 150 °C for two hours, and gradually cooled to 23 °C over eight hours. A liquid containing a precipitate obtained from propylene polymer was filtered under reduced pressure with a standard 25G4 glass filter manufactured by Tokyo Garasu Kikai Co., Ltd. 100 ml of the filtrate were recovered and dried under reduced pressure to obtain a decane-soluble fraction, and this weight was measured with an accuracy of 10-4 g (this weight was indicated by a (g) in the following formula).After this operation, the amount of the decane-soluble portion was determined by the following formula.

[093] Content of the soluble part in decane = 100 x (500 xa) / (100 xb) Content of the insoluble part in decane = 100 - 100 x (500 xa) / (100 xb).

[094] (4) Molecular weight distribution (MWD): Gel permeation chromatograph: HLC-8321 type GPC / HT, Petition 870250087268, dated 09 / 26 / 2025, page 50 / 94 39 / 79 manufactured by Tosoh Corporation.

[095] Detector: Differential refractometer.

[096] Column: Two TSKgel GMH6-HTs and two TSKgel GMH6-HTLs, manufactured by Tosoh Corporation, were connected in series.

[097] Mobile phase medium: o-dichlorobenzene.

[098] Flow rate: 1.0 ml / minute.

[099] Measurement temperature: 140 °C.

[100] Method for creating the calibration curve: A standard sample of polystyrene was used.

[101] Sample concentration: 0.1% (w / w).

[102] Sample solution quantity: 0.4 ml.

[103] The measurement was performed under the conditions described above. The resulting chromatogram was analyzed using a known method to calculate the weight-average molecular weight (Mw), the number-average molecular weight (Mn), the Z-average molecular weight (Mz), the Mw / Mn value, and the Mz / Mw value, which are molecular weight distribution (MWD) indices. The measurement time per sample was 60 minutes.

[104] (5) Melting point (Tm) of the polymer: The melting point (Tm), crystallization temperature (Tc), and heat of fusion (ΔH) of the polymer of the present invention were measured using a differential scanning calorimeter (DSC), a DSC 8000 device manufactured by PerkinElmer Co., Ltd. 3 to 10 mg of a sample were sealed in an aluminum pan and heated from room temperature to 200 °C at 100 °C / minute. This sample was held at 200 °C for five minutes and then cooled to 30 °C at 10 °C / minute. The maximum temperature observed in this cooling test was considered the crystallization temperature (Tc), and the amount of heat generated, specified by the peak area, was considered as Δη. Subsequently, the sample was held at 30 °C for five minutes and then heated a second time to 200 °C at 10 °C / minute. The maximum temperature observed in this second test was... Petition 870250087268, dated 09 / 26 / 2025, page 51 / 94 40 / 79 heating test was considered as the melting point (Tm).

[105] The final melting point (Tmf) of the polymer of the present invention was measured using a differential scanning calorimeter (DSC), the DSC 8000 device, manufactured by PerkinElmer Co., Ltd. 3 to 10 mg of a sample were sealed in an aluminum pan and heated from room temperature to 240 °C at 80 °C / minute. The sample was held at 240 °C for one minute and then cooled to 0 °C at 80 °C / minute. The sample was held at 0 °C for one minute, then heated to 150 °C at 80 °C / minute and held for five minutes. Finally, the sample was heated to 180 °C at 1.35 °C / minute, and the intersection between the tangent of the inflection point on the high-temperature side of a peak obtained in this final heating test and the baseline was used as the final melting point (Tmf).

[106] Tmf can be considered as one of the parameters to evaluate, for example, the crystalline structure of a component that exhibits extremely high stereoregularity or the ease of crystallization or the crystalline structure of a polymer in an ultra-high molecular weight region, which is considered to have a tendency to be less likely to crystallize. More specifically, it can be considered that the higher the value of this Tmf, the greater the probability of an ultra-high molecular weight polymeric component forming highly heat-resistant crystals. Example 2 Synthesis of compound 3

[107] Compound 3 shown below was synthesized by a method described below. {Chemistry 34} (Compound 3) Petition 870250087268, dated 09 / 26 / 2025, page 52 / 94 41 / 79

[108] 15.1 g of compound 2 (41.7 mmoles, 1 eq) and 417 mL of THF (dehydrated) were added to a 2 L three-necked flask, dried in an oven containing a magnetic stirring bar in a nitrogen atmosphere, and stirred in an ice bath. 4.55 g of sodium hydride (55%, liquid paraffin dispersion, 104.2 mmoles, 2.5 eq) were added slowly and stirred for 30 minutes in an ice bath. Then, 5.19 mL of iodomethane (83.4 mmoles, 2 eq) were added, and the reaction mixture was stirred at room temperature for four hours. The reaction solution was cooled again in an ice bath, 200 mL of distilled water were added, and extraction was performed twice with ethyl acetate. The combined organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The organic layer was concentrated using a rotary evaporator to obtain 19.5 g of the crude product.The crude product obtained was purified by silica gel column chromatography (eluent: hexane: ethyl acetate = gradient from 2:1 to 1:1) and recrystallized with a mixed solution of hexane and ethyl acetate to obtain 14.0 g of compound 3 (37.2 mmoles, 89% yield, light yellow crystal). The 1H-NMR data of the obtained compound 3 are shown below.

[109] 1H-NMR (400 MHz, CDCl3, TMS as internal standard): δ 7.70 (dt, J = 8.3, 1.5 Hz, 2 H), 7.50 (t, J = 7.9 Hz, 1 H), 7.36-7.32 (m, 2 H), 7.29-7.25 (m, 1 H, superimposed on the signal of residual CHCl3), 7.22 (dd, J = 8.3, 7.3 Hz, 1 H), 7.13-7.08 (m, 1 H), 7.06-6.97 (m, 3 H), 3.76-3.65 (m, 1 H), 3.52-3.31 (m, 6 H), 1.28 (t, J = 7.2 Hz, 3H), 1.18 (t, J = 7.2 Hz, 3 H). Example 3 Synthesis of compound 4

[110] Compound 4 shown below was synthesized by a method described below, according to the following reaction formula. Petition 870250087268, dated 09 / 26 / 2025, page 53 / 94 42 / 79 {Chemistry 35} (Compound 4) {Chemistry 36} Intermediate 2 K2CO3 MeOH, 40°C Compound 4

[111] 2.93 g of 8-amino-1-naphthol hydrochloride (15.0 mmol, 1 eq) and 60 mL of chloroform (dehydrated) were added to a 300 mL three-necked flask, dried in an oven, containing a heated magnetic stir bar in a nitrogen atmosphere. Then, 5.93 g of pyridine (dehydrated) (75.0 mmol, 5 eq) were added dropwise at room temperature. After cooling the reaction solution in an ice bath, 5.52 g of o-toluene chloride (35.7 mmol, 2.4 eq) were added dropwise. After the dropwise addition was complete, the reaction solution was stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 15 mL of methanol were added, and the reaction solution was stirred at room temperature for 30 minutes. Water and dichloromethane were added, and the extraction was performed four times with dichloromethane.A combined organic layer was dried over sodium sulfate and then concentrated with a rotary evaporator. 9.00 g of the crude product obtained were purified by silica gel column chromatography (eluent, hexane:ethyl acetate = gradient 95:5 to 90:10) to obtain 5.03 g of intermediate 2. 5.03 g of intermediate 2, 100 mL of methanol and 2.29 g of potassium carbonate (16.6 mmol) were added to a 300 mL round-bottom flask, and the solution... Petition 870250087268, dated 09 / 26 / 2025, page 54 / 94 43 / 79 was stirred at 40 °C for two hours. After the reaction was complete, water and ethyl acetate were added, extraction was performed four times with ethyl acetate, and extraction was performed twice with dichloromethane. The combined organic layer was dried over sodium sulfate and then concentrated with a rotary evaporator to obtain a brown solid crude product. Furthermore, the reaction was carried out again on a third scale to obtain a crude product. The crude products from both reactions were combined, ultrasonically washed with hexane, and filtered to obtain 4.54 g (16.4 mmol) of compound 4. The XH-NMR data of the obtained compound 4 are shown below. [112PH-NMR (400 MHz, CDCI3, TMS as internal standard) : δ 2.53 (s, 3 H), 6.75 (dd, J = 1.0, 7.6 Hz, 1 H) , 7.18-7.27 (m, 4 H, superimposed on the residual CDCI3 signal), 7.33 (td, J = 1.3, 7.4 Hz, 1 H), 7.40-7.49 (m, 2 H) , 7.52-7.60 (m, 2 H) , 8.82 (d, J = 7.3 Hz, 1 H), 11.00 (s, 1 H) . Synthesis of compound 5

[113] Compound 5 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 37} Compound 4 Compound 5 Petition 870250087268, dated 09 / 26 / 2025, page 55 / 94 44 / 79

[114] 3.19 g of compound 4 (11.5 mmol, 1 eq) and 60 mL of pyridine (dehydrated) were added to a 300 mL three-necked flask, dried in an oven, containing a heated magnetic stirring bar in a nitrogen atmosphere. Then, 3.90 mL of diethylcarbamoyl chloride (30.8 mmol, 2.7 eq) were added dropwise at room temperature, and the solution was refluxed for 16 hours. After the reaction was complete, the reaction solution was cooled in an ice bath, 30 mL of water were added, and the reaction solution was stirred at room temperature for 30 minutes. Water and ethyl acetate were added, and extraction was performed three times with ethyl acetate. The combined organic layer was washed with water three times, washed again with brine once, dried over sodium sulfate, and then concentrated in a rotary evaporator.4.61 g of the crude product obtained were purified by silica gel column chromatography (eluent, eluent, hexane:ethyl acetate = gradient from 90:10 to 80:20) to obtain 3.51 g of compound 5 (9.32 mmoles, 81% yield). The 1H-NMR data of the obtained compound 5 are presented below.

[115] 1H-NMR (400 MHz, CDCl3, TMS as internal standard): δ 0.93-1.06 (m, 6 H), 2.52 (s, 3 H), 2.80-2.99 (m, 2 H), 3.15-3.26 (m, 2 H), 7.05 (br d, J = 7.6 Hz, 1 H), 7.18-7.29 (m, 2 H, superimposed on the residual CHCl3 signal), 7.32-7.38 (m, 1 H), 7.39-7.44 (m, 1 H), 7.47-7.57 (m, 2 H), 7.66 (dd, J = 0.9, 8.2 Hz, 1 H), 7.72 (dd, J = 0.9, 8.2 Hz, 1 H), 8.66 (m, 1 H), 9.52 (br s, 1 H). Example 4 Synthesis of compound 6

[116] Compound 6 shown below was synthesized by a method described below, according to the following reaction formula. Petition 870250087268, dated 09 / 26 / 2025, page 56 / 94 45 / 79 {Chemistry 39} {Chemistry 40} (Compound 6) Compound 5 1) NaH, THF / DMF °C 2) Honey, THF / DMF 0°C at room temperature

[117] 2.45 g of compound 5 Compound 6 (6.50 mmoles, 1 eq), 6 mL of tetrahydrofuran (dehydrated) and 4 mL of N,N'-dimethylformamide (dehydrated) were added to a three-necked flask of 200 mL, dried in an oven containing a heated magnetic stirring bar in a nitrogen atmosphere. After cooling the reaction solution in an ice bath, 0.37 g of sodium hydride (55% liquid paraffin dispersion, 8.50 mmol, 1.3 eq) was added. After stirring the reaction solution for 50 minutes, 1.11 mL of iodomethane (17.8 mmol, 2.7 eq) was added dropwise. The reaction solution was stirred for 20 minutes, then warmed to room temperature and stirred for a further 18.5 hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 10 mL of water were added, and the reaction solution was stirred at room temperature for 30 minutes. Water and ethyl acetate were added, and extraction was performed three times with ethyl acetate.The combined organic layer was washed three times with water, then washed once with brine, dried over sodium sulfate, and then concentrated in a rotary evaporator to obtain 3.13 g of the crude product. Along with 1.74 g of the crude product obtained by separately carrying out the same reaction described above on a small scale, the crude product was purified by silica gel column chromatography (eluent: hexane: ethyl acetate =). Petition 870250087268, dated 09 / 26 / 2025, page 57 / 94 46 / 79 gradient from 80:20 to 70:30) to obtain 3.75 g of compound 6 (9.16 mmol). The XH-NMR data of the obtained compound 6 are shown below. [118PH-NMR (400 MHz, CDCl3, TMS as internal standard): δ 1.29 (dt, J = 7.2, 25.1 Hz, 6 H), 2.46 (s, 3 H), 3.33-3.44 (m, 5H), 3.58 (m, 1 H), 3.86 (m, 1 H), 6.62-6.67 (m, 1 H), 6.91 (td,J = 7.3, 8.3 Hz, 1 H), 6.98-7.05 (m, 3 H), 7.17 (dd, J = 7.3,8.3 Hz, 1 H), 7.29 (dd, J = 1.1, 7.7 Hz, 1 H), 7.48 (t, J = 7.9 Hz, H) , 7, 63-7, 68 (m, 2 H) . Example 5 Synthesis of compound 7

[119] Compound 7 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 41} (Compound 7) {Chemistry 42} 1) NaH, THF / DMF 0 °C 2) lodomethane, THF / DM 0C° at temperature (Compound 2) (Compound 7)

[120] 2.89 g of compound 2 (7.9 mmoles, 1 eq), 45 mL of tetrahydrofuran (dehydrated), and 9 mL of N,N-dimethylformamide (dehydrated) were added to a 200 mL three-necked flask, dried in an oven, containing a heated magnetic stirring bar in a nitrogen atmosphere. The solution was then cooled in an ice bath, 0.44 g of sodium hydride (55%, liquid paraffin dispersion, 10.0 mmoles, 1.3 eq) was then added slowly, and the solution was stirred for 30 minutes. Then, 1.36 g of iodomethane was added. Petition 870250087268, dated 09 / 26 / 2025, page 58 / 94 47 / 79 (8.7 mmoles, 1.1 eq) was added dropwise. After the dropwise addition was complete, the reaction solution was heated to room temperature and stirred for 19 hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 3 mL of water were added, and the reaction solution was stirred at room temperature for 30 minutes. Water and ethyl acetate were added to the reaction solution, extraction was then performed once with ethyl acetate, and the organic phase was washed three times with water and once with brine. The combined organic layer was dried over magnesium sulfate and concentrated in a rotary evaporator.The crude product obtained was purified by silica gel column chromatography (development solvent as eluent, hexane:ethyl acetate = gradient 100:0 to 70:30) and ODS column chromatography (water and methanol were used as a development solvent as eluent, water:methanol = gradient 100:0 to 55:45) to obtain 1.59 g (4.1 mmoles, 51% yield, white crystal) of compound 7. The 1H-NMR data of the obtained compound 7 are shown below.

[121] 1H-NMR (400 MHz, CDCl3, TMS as internal standard): δ 7.74-7.69 (m, 2 H), 7.52 (t, J = 7.9 Hz, 1 H), 7.35-7.29 (m, 3 H), 7.19 (dd, J = 8.3, 7.3 Hz, 1 H), 7.11 (tt, J = 7.3, 1.7 Hz, 1 H), 7.03 (tt, J = 7.4, 1.5 Hz, 2 H), 6.87 (dd, J = 7.3, 1.2 Hz, 1 H), 4.58 (td, J = 13.7, 6.7 Hz, 1 H), 3.69 (td, J = 14.4, 7.1 Hz, 1 H), 3.51-3.33 (m, 3 H), 3.23 (dt, J = 20.3, 7.0 Hz, 1 H), 1.25 (t, J = 7.2 Hz, 3 H), 1.18 (td, J = 7.0, 4.0 Hz, 6 H). Example 6 Synthesis of compound 8

[122] Compound 8 shown below was synthesized by a method described below, according to the following reaction formula. Petition 870250087268, dated 09 / 26 / 2025, page 59 / 94 48 / 79 {Chemistry 43} OH NH2 (Compound 8) {Chemistry 44} NH2nh2 NaHSOs (aq sat) EtOH, reflux 2)6MKOHaq.,reflux OH NH2

[123] 51.4 g of 1,8-diaminonaphthalene (324.6 mmol) and 171.2 mL of ethanol were added to a 2 L three-necked flask, dried in an oven containing a heated magnetic stir bar, in a nitrogen atmosphere, and stirred at room temperature. Then, 342.4 mL of a saturated aqueous solution of sodium hydrogen sulfite were added dropwise at room temperature. After the dropwise addition was complete, the solution was heated and refluxed for 24 hours. Then, the solution was cooled to room temperature, 171.2 mL of an aqueous solution of potassium hydroxide (6 moles / L) were added, and the solution was heated and refluxed for 3.5 hours. Then, the solution was cooled to room temperature, and 2.5 L of hydrochloric acid (2 moles / L) were added.The resulting aqueous solution was removed, extracted three times with 500 mL of ethyl acetate, and the target compound was extracted to an aqueous layer from a combined organic layer using 500 mL of hydrochloric acid (1 mol / L). 300 mL of a saturated aqueous solution of sodium carbonate were added to the aqueous layer, and extraction was performed with 500 mL of ethyl acetate. The combined organic layer was dried over magnesium sulfate and concentrated in a rotary evaporator to obtain 33.81 g (65% yield) of 8-amino-1-naphthol. Synthesis of compound 9

[124] Compound 9 shown below was synthesized by a method described below, according to the following formula of Petition 870250087268, dated 09 / 26 / 2025, pp. 60 / 94 49 / 79 reaction. {Chemistry 45} (Compound 9) The {Chemistry 46} temperature o ~nambient (rt) ~ □_ n Compound 8 Compound 9

[125] 15.6 g of compound 8 (98.1 mmoles, 1 eq) and 156 mL of ethanol were added to a 1 L three-necked flask, dried in an oven containing a heated magnetic stir bar in a nitrogen atmosphere, and stirred while cooling in a water bath. Then, 21.3 mL of diethyl dicarbonate (147.2 mmoles, 1.5 eq) and 1.41 g of guanidine hydrochloride (14.7 mmoles, 0.15 eq) were added, and the solution was stirred at room temperature for 1.5 hours. The reaction solution was concentrated, and 300 mL of distilled water and 300 mL of ethyl acetate were added to the resulting residue. Extraction was performed three times with ethyl acetate, and the combined organic layer was dried over magnesium sulfate and concentrated in a rotary evaporator.The crude product obtained was purified by silica gel column chromatography twice (one eluent the first time: chloroform / methanol, one eluent the second time: hexane / ethyl acetate) to obtain 16.2 g of compound 9 (70.1 mmoles, 71% yield). Synthesis of compound 10

[126] Compound 10 shown below was synthesized by a method described below, according to the following reaction formula. Petition 870250087268, dated 09 / 26 / 2025, pp. 61 / 94 50 / 79 {Chemistry 47} (Compound 10) {Chemistry 48} Pyridine, reflux. Compound 9 Compound 10

[127] 16.2 g of compound 9 (69.9 mmol, 1 eq) and 300 mL of pyridine (dehydrated product) were added to a 1 L three-necked flask, dried in an oven containing a magnetic stirring bar in a nitrogen atmosphere. 9.30 mL of N,N-diethylcarbamoyl chloride (73.4 mmol, 1.05 eq) were then added and the temperature was raised to 120 °C to heat and reflux the solution. After four hours, the reaction solution was cooled to room temperature, and 500 mL of distilled water were added. An aqueous layer was extracted with diethyl ether three times, the combined organic layer was washed once with hydrochloric acid (1 mol / L) and a saturated aqueous solution of sodium bicarbonate, and the organic layer was then dried over anhydrous magnesium sulfate and concentrated in a rotary evaporator.The crude product obtained was purified by silica gel column chromatography twice (eluent first time: chloroform / methanol, eluent second time: hexane / ethyl acetate) and subsequently washed with a mixed solvent of hexane and ethyl acetate in a 9:1 ratio, to obtain 13.95 g of compound 10 (60% yield). The XH-NMR data of the obtained compound 10 are presented below.

[128] 1H-NMR (500 MHz, CDC13, TMS as internal standard): δ 1.25 (t, J = 7.5 Hz, 3 H), 1.31 (t, J = 7.0 Hz, 3 H), 1.37 (t, J = 7.5 Hz, 3 H), 3.46 (q, J = 7.5 Hz, 2 H), 3.61 (q, J = 7.5 Hz, 2 Petition 870250087268, dated 09 / 26 / 2025, pp. 62 / 94 51 / 79 Η), 4.23 (q, J = 7.0 Hz, 2 H), 7.08-7.10 (m, 1 H), 7.39-7.46 (m, H), 7.57-7.58 (m, 1 H), 7.68-7.70 (m, 1 H), 8.20 (br s, 1 H), 8.50 (br s, 1 H) . Example 7 Synthesis of compound 11

[129] Compound 11 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 49} (Compound 11) {Chemistry 50} 1) NaH, THF 0°C 2) Honey, THF / DMF 0°C, at room temperature (Compound 10) (Compound 11)

[130] 21.6 g of compound 10 (65.5 mmol) and 655 mL of tetrahydrofuran (dehydrated) were added to a 3 L three-necked flask, dried in an oven, containing a heated magnetic stirring bar in a nitrogen atmosphere, and the reaction solution was cooled in an ice bath. 3.43 g of sodium hydride (55%, product dispersed in liquid paraffin, 78.6 mmol, 1.2 eq) were added slowly and, after one hour, 4.28 mL of iodomethane (67.8 mmol, 1.05 eq) were added dropwise. After the dropwise addition was complete, the reaction solution was heated to room temperature and stirred at room temperature for one hour. After cooling the reaction solution in an ice bath, 300 mL of distilled water were added dropwise. The reaction solution was extracted three times with ethyl acetate, and the combined organic layer was washed with brine, dried over magnesium sulfate, and Petition 870250087268, dated 09 / 26 / 2025, pp. 63 / 94 52 / 79 concentrated in a rotary evaporator. The crude product obtained was purified by multiple rounds of silica gel column chromatography to obtain 5.35 g of compound 11 (24% yield). [131PH-NMR (500 MHz, CDCI13, TMS as internal standard): δ 0.98-1.37 (m, 9 H), 3.23-4.29 (m, 9 H), 7.12-7.14 (m, 1 H), 7.26 7.34 (m, 1 H, superimposed on the residual CHCl3 signal), 7.42-7.47 (m, 2 H), 7.74-7.75 (m, 1 H), 7.80-7.82 (m, 1 H).

[132] *Since a rotamer was contained, an integral value of the signals derived from protons at the same locations in the structure was summed to obtain an integer value. Example 8 Synthesis of compound 12

[133] A compound 12 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 51} {Chemistry 52} (Compound 12) 1) NaH, THF °C (Compound 10) 2) THF / DMF lodomethane at 0 °C at room temperature (Compound 12)

[134] 3.61 g of compound 10 (10.9 mmoles, 1 eq) and 54 mL of tetrahydrofuran (dehydrated) were added to a 200 mL three-necked flask, dried in an oven, containing a heated magnetic stirring bar in a nitrogen atmosphere. The solution was then cooled in an ice bath, 0.50 g of sodium hydride (55%, liquid paraffin dispersion, 11.6 mmoles, 1 eq) was then slowly added and the solution was stirred for 30 minutes. Then, 1.88 g of Petition 870250087268, dated 09 / 26 / 2025, pp. 64 / 94 53 / 79 Iodomethane (12.0 mmol, 1.1 eq) was added slowly dropwise. After the dropwise addition was complete, the solution was heated to room temperature and stirred for 20 hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 0.53 g of ethanol (11.6 mmol, 1.1 eq) was added, and the solution was stirred at room temperature for 30 minutes. The reaction solution was concentrated in a rotary evaporator. The crude product obtained was purified by silica gel column chromatography (eluent: hexane:ethyl acetate = gradient from 100:0 to 76:24) and then purified by recrystallization with a mixed solvent of hexane and dichloromethane to obtain 2.57 g (7.18 mmoles, 66% yield, white crystal) of compound 12. The XH-NMR data of the obtained compound 12 are presented below.

[135] XH-NMR (400 MHz, CDCI3, TMS as internal standard) : δ 7.83 (dd, J = 8.3, 1.0 Hz, 1 H) , 7.74 (dd, J = 8.3, 1.0 Hz, 1 H) , 7.44 (q, J = 7.6 Hz, 2 H), 7.23 (dd, J = 7.3, 1.2 Hz, 1 H), 7.13 (dd, J = 7.6, 1.0 Hz, 1 H), 4.16-3.96 (m, 3 H), 3.79-3.17 (m, 5 H), 1.28 (t, J = 7.2 Hz, 3 H), 1.22 (t, J = 7.1 Hz, 3 H), 1.17 (t, J = 7.2 Hz, 3 H), 1.01 (t, J = 7.2 Hz, 3H). Example 9 Synthesis of imidazolium salt 1

[136] An imidazolium salt 1 shown below was synthesized according to the following reaction formula by a method described below for the purpose of using the imidazolium salt 1 for the synthesis of a compound 13 described below. {Chemistry 53} X1 (Imidazolium Salt 1) {Chemistry 54} O O O O Θ Ü Et2NH_________________ [I Mel____________1oCH2Cl2,°°c àj CN MecN'à temp· jn NONÍMetemperatura ' ambient,© ambient, (Intermediate 3)24h(Imidazolium salt 1) 24h Petition 870250087268, dated 09 / 26 / 2025, pp. 65 / 94 54 / 79

[137] 53.5 g of carbonylimidazole (330 mmoles, 1.1 eq) and 200 mL of dichloromethane (dehydrated) were added to a 500 mL three-necked flask, dried in an oven, containing a heated magnetic stirring bar in a nitrogen atmosphere, and the reaction solution was cooled in an ice bath. After cooling, 21.9 g of diethylamine (300 mmoles, 1 eq) were added dropwise over 20 minutes. After the dropwise addition was complete, the reaction solution was slowly heated to room temperature and stirred for 24 hours, then kept at room temperature. The reaction solution was cooled again in an ice bath, and 200 mL of water were added dropwise. The extraction was performed four times with dichloromethane, the combined organic layer was dried over sodium sulfate and concentrated in a rotary evaporator to obtain 56.3 g of an intermediate 3 with a purity of 78%.

[138] The intermediate 3 obtained by the method described above was transferred to a 1 L reaction vessel, the interior was replaced with nitrogen, 500 mL of acetonitrile (dehydrated) and 181.4 g of iodomethane (1.28 mol, 4.9 eq) were added, and the solution was stirred at room temperature for 24 hours. Then the solution was concentrated in its entirety to obtain 111.7 g of imidazolium salt 1 with a purity of 81.3%. Synthesis of compound 13

[139] Compound 13 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 55} Petition 870250087268, dated 09 / 26 / 2025, pp. 66 / 94 55 / 79 {Chemistry 56} (Compound 8) Intermediate 4 (Compound 13)

[140] 52.5 g of imidazolium salt 1 (138 mmoles, 1.1 eq), 500 mL of acetonitrile (dehydrated), 19.9 g of compound 8 (125 mmoles, 1 eq), and 15.2 g of triethylamine (150 mmoles, 1.2 eq) were sequentially added to a 1 L four-necked flask, dried in an oven containing a heated magnetic stirring bar in a nitrogen atmosphere. The temperature was raised until the internal temperature of the reaction solution reached 78.5 °C, and the reaction solution was heated and refluxed for 18 hours. The reaction solution was then cooled to room temperature and concentrated. 500 mL of dichloromethane were added to the resulting black oil, and the resulting solid was filtered. 400 mL of water were added to the filtrate, and the extraction was performed four times with dichloromethane.The combined organic layer was washed three times with water, then washed once with brine, dried over sodium sulfate, and concentrated in a rotary evaporator. The crude product obtained was purified by silica gel column chromatography (hexane:ethyl acetate = 50:50) to obtain 29.5 g of a mixture containing intermediate 4.

[141] 27.4 g of the mixture containing intermediate 4 (75% NMR purity, 80 mmol, 1 eq) and 500 mL of tetrahydrofuran (dehydrated) were added to a 1 L four-necked flask, dried in an oven, fitted with a magnetic stirrer in a nitrogen atmosphere, and cooled in an ice bath. Then, 56 mL of denBuLi (hexane solution, 1.57 mol / L, 88 mmol, 1.1 eq) were added dropwise over 20 minutes. After the dropwise addition was complete, the temperature was Petition 870250087268, dated 09 / 26 / 2025, pp. 67 / 94 56 / 79 raised until the internal temperature reached 65 °C, and the reaction solution was heated and refluxed for 17 hours. Then the reaction solution was cooled in an ice bath and 100 mL of water were added. The extraction was performed three times with ethyl acetate, and the combined organic layer was washed with water three times and then with brine once. The organic layer was dried over sodium sulfate and then concentrated in a rotary evaporator. The crude product obtained was purified by multiple rounds of silica gel column chromatography to obtain 5.33 g of compound 13 (19% yield). Example 10 Synthesis of compound 14

[142] 0 compound 14 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 57} (Compound 14) reflux {Chemistry 58} (Compound 1) (Compound 14)

[143] 3.03 g of compound 1 (11.5 mmoles, 1 eq) and mL of pyridine (dehydrated) were added to a 300 mL three-necked flask dried in an oven containing a heated magnetic stir bar in a nitrogen atmosphere. Then 3.63 mL of chloride 1-piperidinecarbonyl (28.8 mmol 2.5 eq) were added slowly dropwise at room temperature and the solution was heated and refluxed for 26.5 hours (oil bath at 115 °C, internal temperature Petition 870250087268, dated 09 / 26 / 2025, pp. 68 / 94 57 / 79 at 115 °C). After the reaction was complete, the reaction solution was cooled in an ice bath, 30 mL of water were slowly added, and the reaction solution was stirred at room temperature for 30 minutes. After the addition of water and ethyl acetate, extraction was performed twice with ethyl acetate and then twice with dichloromethane. The combined organic layer was washed three times with water, sodium bicarbonate was added to the aqueous layer, and extraction was performed three times with dichloromethane. The combined organic layer was dried over sodium sulfate and then concentrated in a rotary evaporator. 5.40 g of the crude product obtained were purified by silica gel column chromatography (eluent: hexane:dichloromethane = gradient from 50:50 to 0:100) to obtain 3.43 g of compound 14 (9.16 mmoles, 80% yield). The 1H—NMR data for compound 14 obtained are presented below.

[144] 1H-NMR (400 MHz, CDC13, TMS as internal standard): δ 1.33 (br s, 2 H), 1.48 (br s, 4 H), 3.28 (m, 4 H), 7.09 (dd, J = 1.2, 7.6 Hz, 1 H), 7.32-7.45 (m, 1 H), 7.48-7.60 (m, 4 H), 7.70 (dd, J = 1.0, 8.3 Hz, 1 H), 7.74 (dd, J = 1.0, 8.3 Hz, 1 H), 7.887.93 (m, 2 H), 8.32 (br d, J = 6.8 Hz, 1 H), 9.41 (br s, 1 H) . Example 11 Synthesis of compound 15

[145] Compound 15 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 59} (Compound 15) Petition 870250087268, dated 09 / 26 / 2025, p. 69 / 94 58 / 79 1) NaH, THF / DMF 0 °C (Compound 14) 2) Honey, THF / DMF °C at room temperature

[146] 2.32 g of compound 14 (Compound 15) (6.20 mmol, 1 eq), 36 mL of tetrahydrofuran (dehydrated), and 4 mL of N,N'-dimethylformamide (dehydrated) were added to a 200 mL three-necked flask, dried in an oven with a magnetic stir bar in a nitrogen atmosphere. After cooling the reaction solution in an ice bath, 0.35 g of sodium hydride (55%, product dispersed in liquid paraffin, 8.10 mmol, 1.3 eq) was added slowly. After stirring the reaction solution for 40 minutes, 0.46 mL of iodomethane (7.40 mmol, 1.2 eq) was added slowly dropwise. The reaction solution was stirred for 20 minutes, then slowly warmed to room temperature and stirred again for 19 hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 10 mL of water were added slowly, and the reaction solution was stirred at room temperature for 30 minutes.Water and ethyl acetate were added, and extraction was performed three times with ethyl acetate. The combined organic layer was washed three times with water, then washed once with brine, dried over sodium sulfate, and then concentrated in a rotary evaporator. As a purification result, 2.77 g of the crude product obtained by silica gel column chromatography (eluent: hexane: ethyl acetate = gradient from 85:15 to 0:100) yielded 2.26 g of compound 15 (6.20 mmoles, 94% yield). The XH-NMR data of the obtained compound 15 are presented below.

[147] 1H-NMR (400 MHz, CDCl3, TMS as internal standard): δ 1.52-1.81 (m, 6 H), 3.39-3.79 (m, 7 H), 6.98 (dd, J = 1.2, 7.3 Hz, 1 H), 7.00-7.06 (m, 2 H), 7.08-7.14 (m, 1 H), 7.21 (dd, J = Petition 870250087268, dated 09 / 26 / 2025, pp. 70 / 94 59 / 79 7.3, 8.0 Hz, 1 Η), 7.28 (dd, J = 1.1, 7.7 Hz, 1 H), 7.32-7.36 (m, 2 H), 7.50 (t, J = 7.9 Hz, 1 H), 7.71 (dd, J = 3.5, 7.2 Hz, 2 H). Example 12 Synthesis of compound 16

[148] Compound 16 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 61} Br (Compound 16) —O {Chemistry 62}

[149] 50.0 g of 2,5-dimethylanisole (367 mmol) and 0.65 g of iron powder (11.6 mmol) were placed in a 300 mL four-necked flask, dried in an oven, containing a heated magnetic stirring bar, and 58.7 g of bromine (367 mmol) were added dropwise at room temperature over 38 minutes while the solution was cooled in a water bath. The solution was stirred again at room temperature for two hours. The reaction solution was cooled in an ice bath, 200 mL of hexane and 100 mL of water were added, a small amount of sodium thiosulfate was added to change the color, and sodium hydroxide was added to neutralize the reaction solution. The reaction solution was extracted with hexane, the combined organic layer was washed with brine, then dried over sodium sulfate and concentrated in a rotary evaporator. 84.4 g of the crude product obtained were vacuum distilled to obtain 44.86 g of compound 16 (56% yield). Petition 870250087268, dated 09 / 26 / 2025, pp. 71 / 94 60 / 79 Synthesis of compound 17

[150] 0 Compound 17 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 63} (Compound 17) —O {Chemistry 64} Br MgBr \_Bry— rAMgr>- ~λΥ~ / 7 THF / 7Co(acac)3, TMEDA ~0THF “° (Compound 16) intermediate 5 (Compound 17)

[151] 3.65 g of magnesium (150 mmol) were placed in a 200 mL four-necked flask, dried in an oven containing a heated magnetic stirring bar, and heated and dried under reduced pressure. The interior was replaced with nitrogen, 40 mL of tetrahydrofuran were placed there, several drops of 1,2-dibromoethane were added and heated, and gentle reflux was maintained while 22.09 g of compound 16 (tetrahydrofuran solution, 100 mmol, 40 mL) were added dropwise from a dropping funnel. The resulting product was stirred to room temperature to obtain a solution containing an intermediate 5.

[152] 1.78 g of cobalt(III) tris(acetylacetonate), 0.75 mL of tetramethylethylenediamine (5.00 mmol) and 14.0 mL of 2-bromopropane (149 mmol) were placed in a 500 mL four-necked flask, dried in an oven containing a heated magnetic stirring bar in a nitrogen atmosphere, and cooled in an ice bath. The solution of intermediate 5, prepared by the procedure of the previous section, was added dropwise from a dropping funnel over 45 minutes. The solution was stirred for one hour and 20 minutes. Petition 870250087268, dated 09 / 26 / 2025, pp. 72 / 94 61 / 79 remaining cooled in an ice bath. Then, 1 mol / L hydrochloric acid was added dropwise, and the reaction was stopped. After the reaction, the solution was extracted with diethyl ether, the combined organic layer was washed with an aqueous solution of sodium carbonate and brine, then dried over sodium sulfate and concentrated in a rotary evaporator. 18.38 g of the crude product obtained were vacuum distilled to obtain 15.9 g of compound 17 with a yield of 86%. Synthesis of compound 18

[153] 0 Compound 18 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 65} (Compound 18) HO {Chemistry 66}BBr3__► yaZ \= / ch2ci2\= / —o HO

[154] 18.38 g of compound 17 (93.9 mmol) and 125 mL of dichloromethane were placed in a 500 mL four-necked flask, dried in an oven containing a heated magnetic stir bar, and cooled in an ice bath. While the solution was being stirred, 100 mL of a boron tribromide dichloromethane solution (1 mol / L concentration) was added dropwise from a dropping funnel over 30 minutes, maintaining the internal temperature between 3 °C and 7 °C. The solution was then stirred at room temperature for two hours, and water was subsequently added dropwise while the solution was cooled in an ice water bath. Extraction was then performed with dichloromethane, and the combined organic layer was washed with aqueous sodium bicarbonate solution. Petition 870250087268, dated 09 / 26 / 2025, pp. 73 / 94 62 / 79 and brine, then dried over sodium sulfate and concentrated in a rotary evaporator. 17.2 g of the crude product obtained were purified by silica gel column chromatography (using an eluent containing toluene and ethyl acetate in a 100:1 ratio) to obtain 14.0 g of compound 18 with a yield of 88%. Synthesis of compound 19

[155] Compound 19 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 67} (Compound 19) HO NO2{Chemistry 68} 70%hno3__( / Ά__ _______1^ __( / V__ \= / ch2ci2\=( HO HO NO2

[156] 41.9 g of compound 18 (249 mmol) and 290 ml of dichloromethane were placed in a four-necked flask of L, dried in an oven containing a heated magnetic stirring bar, and stirred while cooling in an ice bath. 17.4 ml of nitric acid (70%, 274 mmol) were added dropwise over 36 minutes, while the internal temperature was maintained between 0.3 °C and 2.3 °C. The solution was then stirred in an ice bath for 21 hours and subsequently stirred at room temperature for five hours. 300 ml of an aqueous sodium bicarbonate solution were then added, and the organic layer was extracted with dichloromethane. The combined organic layer was dried over sodium sulfate and concentrated in a rotary evaporator to obtain 54.3 g of the crude product. The crude product was diluted with 100 ml of hexane and kept at room temperature for 64 hours to remove Petition 870250087268, dated 09 / 26 / 2025, pp. 74 / 94 63 / 79 of the crystals precipitated. A supernatant was purified by silica gel column chromatography (using a mixed solvent of hexane and acetone in a 95:5 ratio) to obtain 17.69 g of compound 19 with a yield of 33%. Synthesis of compound 20

[157] 0 compound 20 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 69} HO NO2HO NH2

[158] 17.69 g of compound 19 (82.4 mmoles), 2.0 g of Pd / C (5%, 55% water) and 100 mL of ethanol were placed in a 200 mL autoclave, dried in an oven, containing a heated magnetic stirring bar, and the interior was replaced in a nitrogen atmosphere under stirring. The interior was pressurized so that the hydrogen pressure was maintained between 0.6 and 0.9 MPa while the solution was stirred at 50 °C. The solution was stirred for 22 hours until the decrease in hydrogen pressure was stopped, hydrogen was then discharged, and the interior was replaced in a nitrogen atmosphere. A precipitate in the container was dissolved by the addition of tetrahydrofuran and filtered with a hydrophilic PTFE membrane filter with a pore diameter of 1 μm. The filtrate was concentrated in a rotary evaporator and placed in a 200 mL autoclave, dried in an oven containing a heated magnetic stirring bar.In addition, 100 mL of tetrahydrofuran and 1.0 g of Pd / C (5%, 55% water) were used. Petition 870250087268, dated 09 / 26 / 2025, pp. 75 / 94 64 / 79 added, and the interior was replaced in a nitrogen atmosphere under stirring. The interior was pressurized so that the hydrogen pressure was maintained between 0.6 and 0.9 MPa while the solution was stirred at 50 °C. The solution was stirred for 4.5 hours until the decrease in hydrogen pressure stopped. The hydrogen was then discharged and the interior was replaced in a nitrogen atmosphere. The reaction solution was filtered with a hydrophilic PTFE membrane filter with a pore diameter of 1 μm, and the filtrate was concentrated in a rotary evaporator to obtain a solid crude product. This was washed with hexane and dried under reduced pressure to obtain 14.72 g of compound 20 with a yield of 96%. Synthesis of compound 21

[159] Compound 21 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 71}

[160] 2.20 g of compound 20 (12.3 mmoles, 1 eq) and 65 mL of chloroform (dehydrated) were added to a 200 mL three-necked flask, dried in an oven, containing a heated magnetic stirring bar in a nitrogen atmosphere. The solution was then cooled in an ice bath, and 1.07 g of pyridine (dehydrated, 13.5 mmoles, 1.1 eq) and 1.82 g of benzoyl chloride (12.9 mmoles, 1.1 eq) were added slowly, Petition 870250087268, dated 09 / 26 / 2025, pp. 76 / 94 65 / 79 and the solution was stirred for 10 minutes. Then, the ice bath was removed to raise the temperature to room temperature, and the solution was stirred for six hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 2.0 mL of methanol (49.3 mmoles, 4 eq) were added, and the reaction solution was stirred at room temperature for 30 minutes. Water and ethyl acetate were added to the reaction solution, and the reaction solution was extracted with ethyl acetate, washed with water three times, then washed again with brine once, dried over magnesium sulfate, and then concentrated in a rotary evaporator. 3.50 g of the crude product obtained were dissolved by adding 17 mL of dichloromethane, and 70 mL of hexane were then added with stirring to cool the crude product in an ice bath, thus precipitating a solid.The solid obtained was filtered, collected, and washed with hexane three times to obtain 3.32 g of compound 21 (95% yield). The XH-NMR data of the obtained compound 21 are shown below.

[161] 1H—NMR (400 MHz, CDCl3, TMS as internal standard): δ 7.95-7.92 (m, 2 H), 7.89 (s, 1 H), 7.81 (s, 1 H), 7.63-7.59 (m, 1 H), 7.56-7.51 (m, 2 H) , 7.02 (s, 1 H), 3.16-3.06 (m, 1 H), 2.31 (d, J = 6.6 Hz, 6 H), 1.21 (d, J = 6.8 Hz, 6 H). Synthesis of compound 22

[162] Compound 22 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 73} (Compound 22) Petition 870250087268, dated 09 / 26 / 2025, pp. 77 / 94 66 / 79 {Chemistry 74}

[163] 3.32 g of compound 21 (11.7 mmol, 1 eq) and 40 mL of pyridine (dehydrated) were added to a 100 mL three-necked flask, dried in an oven, containing a heated magnetic stirring bar in a nitrogen atmosphere. Then, 3.99 g of diethylcarbamoyl chloride (29.4 mmol, 2.5 eq) were added while the solution was stirred at room temperature, and the solution was refluxed for 17 hours in an oil bath at 120 °C. After the reaction was complete, the reaction solution was cooled to room temperature and added to 400 mL of ice-cold pure water. The precipitate was filtered with a Kiriyama funnel, washed with pure water three times, and then dried to obtain 3.32 g of the crude product. The crude product obtained was purified by silica gel column chromatography (eluent: hexane: ethyl acetate = gradient from 100:0 to 60:40) to obtain 1.35 g of compound 22.The XH-NMR data for compound 22 obtained (3.5 mmol, 30% yield) are presented below.

[164] 1H-NMR (400 MHz, CDCl3, TMS as internal standard): δ 7.91-7.88 (m, 2 H), 7.80 (s, 1 H), 7.56-7.52 (m, 1 H), 7.49-7.44 (m, 2 H), 7.07 (s, 1 H), 3. 37-3, 30 (m, 4 H), 3.20-3.10 (m, 1 H), 2.23 (d, J = 2.2 Hz, 6 H), 1.22 (d, J = 6.8 Hz, 6 H), 1.07 (dt, J = 13, 3, 5, 9 Hz, 6 H). Example 13 Synthesis of compound 23

[165] Compound 23 shown below was synthesized by a method described below, according to the following reaction formula. Petition 870250087268, dated 09 / 26 / 2025, pp. 78 / 94 67 / 79 {Chemistry 75}

[166] 2.66 g of compound 22 (6.9 mmol, 1 eq) and 45 mL of tetrahydrofuran (dehydrated) were added to a 200 mL three-necked flask, dried in an oven, containing a heated magnetic stir bar in a nitrogen atmosphere. The solution was then cooled in an ice bath, 0.32 g of sodium hydride (55%, liquid paraffin dispersion, 13.3 mmol, 1.9 eq) was added slowly, and the solution was stirred for 10 minutes. Then, 1.09 g of iodomethane (7.7 mmol, 1.1 eq) was added slowly dropwise, and the solution was stirred for 100 minutes. Finally, the solution was warmed to room temperature and stirred for 18 hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 1 mL of methanol (24.7 mmol, 3.6 eq) was added, and the reaction solution was stirred at room temperature for 10 minutes.Next, 10 mL of a saturated aqueous solution of ammonium chloride was added to stop the reaction. Pure water and ethyl acetate were added to the reaction solution, the reaction solution was extracted with ethyl acetate, washed twice with water and once with brine, dried over magnesium sulfate, and then concentrated in a rotary evaporator. 2.97 g of the crude product obtained were suspended in 50 mL of hexane, filtered, and washed with hexane three times to obtain 2.28 g of a crystal. Petition 870250087268, dated 09 / 26 / 2025, pp. 79 / 94 68 / 79 light yellow. The crude product obtained was purified by silica gel column chromatography (eluent: hexane: ethyl acetate = gradient from 100:0 to 80:20) to obtain 2.22 g of compound 23 (5.60 mmoles, 81% yield, white crystal). The XH-NMR data of the obtained compound 23 are presented below.

[167] 1H-NMR (400 MHz, CDCl3, TMS as internal standard): δ 7.30 (brs, 2 H), 7.20 (tt, J = 7.3, 1.6 Hz, 1 H), 7.13-7.08 (m, 2 H), 6.95 (s, 1 H), 3.52-3.31 (m, 4 H), 3.27 (s, 3 H), 2.96 (brs, 1 H), 2.10 (brs, 6 H), 1.28 (t, J = 7.2 Hz, 3 H), 1.25-1.17 (m, 6 H), 1.01 (d, J = 5.6 Hz, 3 H). Example 14 Synthesis of compound 24

[168] Compound 24 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 77} (Compound 24) HO NO2{Chemistry 78} ΛA HNO3 H2O / =\ HO HO NO2

[169] 23.23 g of 4-isopropylphenyl (170.6 mmol) and 65.1 mL of water were placed in a 500 mL three-necked flask, dried in an oven containing a heated magnetic stirring bar in a nitrogen atmosphere, and cooled in an ice bath under stirring. Then, 18.6 mL of nitric acid (67%, 280.8 mmol) were added dropwise over 15 minutes, maintaining the internal temperature at 2.9 °C or less. After 1.5 hours of stirring, 580 mL of water were added, and the reaction solution was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate and then, Petition 870250087268, dated 09 / 26 / 2025, pages 80 / 94 69 / 79 concentrated in a rotary evaporator to obtain 30.23 g of the crude product. The crude product was purified by silica gel column chromatography (eluent: hexane:dichloromethane = gradient from 4:1 to 2:1) to obtain 23.80 g of compound 24 with a yield of 77%. Synthesis of compound 25

[170] Compound 25 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 79}

[171] 23.79 g of compound 24 (131.3 mmoles) and 703.9 ml of ethanol were placed in a 2 L round-bottom flask, dried in an oven, containing a heated magnetic stirring bar. Then, 2.35 g of Pd / C (10%, 55% water) were added, the interior was replaced with a hydrogen atmosphere by connecting a hydrogen balloon to it, and the solution was stirred at room temperature for three hours. The reaction solution was filtered, the filtrate was concentrated, hexane was added to it, a solid obtained by filtration was then washed with hexane and dried to obtain 20.38 g of compound 25 with a yield of 93%. Synthesis of compound 26

[172] Compound 26 shown below was synthesized by a method described below, according to the following reaction formula. Petition 870250087268, dated 09 / 26 / 2025, pp. 81 / 94 70 / 79 {Chemistry 81}

[173] 3.02 g of compound 25 (20.0 mmol, 1 eq) and 100 mL of chloroform (dehydrated) were added to a 500 mL three-necked flask, dried in an oven, containing a heated magnetic stir bar in a nitrogen atmosphere. Then, 1.77 mL of pyridine (dehydrated, 22.0 mmol, 1.1 eq) was added slowly dropwise at room temperature. After cooling the reaction solution in an ice bath, 2.46 mL of benzoyl chloride (21.0 mmol, 1.05 eq) were added slowly dropwise. After the dropwise addition was complete, the reaction solution was heated to room temperature and stirred for four hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 10 mL of methanol were added, and the reaction solution was stirred. Water and dichloromethane were added, and the extraction was then carried out three times with dichloromethane.The combined organic layer was washed with brine once, dried over sodium sulfate, and then concentrated in a rotary evaporator. 5.49 g of the crude product obtained were purified by silica gel column chromatography (eluent: 100% dichloromethane) in two separate runs to obtain 4.90 g (19.2 mmol, 96%) of compound 26. The XH-NMR data of the obtained compound 26 are presented below.

[174] 1H-NMR (400 MHz, CDCI3, TMS as internal standard) : δ 8.43 Petition 870250087268, dated 09 / 26 / 2025, pp. 82 / 94 71 / 79 (s, 1 Η), 8.11 (br s, 1 H), 7.93-7.89 (m 2 H), 7.62-7.56 (m, 1 H), 7.54-7.48 (m, 2 H), 7.05-6.98 (m, 3 H), 2. 92-2.79 (m, 1 H), 1.23 (d, J = 7.1 Hz, 6 H). Synthesis of compound 27

[175] Compound 27 shown below was synthesized by a method described in the reaction. below, according to the following formula from {Chemistry 83} (Compound 27) of compound 26 (15.0 mmoles, 1 eq) and 100 mL of

[176] 3.83 g pyridine (dehydrated) were added to a 300 mL three-necked flask, dried in an oven, containing a heated magnetic stirring bar in a nitrogen atmosphere. Then, 4.75 mL of diethylcarbamoyl chloride (37.5 mmoles, 2.5 eq) were added slowly dropwise at room temperature, and the solution was heated and refluxed for 22.5 hours. After the reaction was complete, the reaction solution was cooled in an ice bath, 30 mL of water were added slowly, and the reaction solution was stirred at room temperature. Then, the reaction solution was concentrated on a rotary evaporator, water and ethyl acetate were added, and the reaction solution was extracted with ethyl acetate three times. The combined organic layer was washed with water three times and with brine once, dried over sodium sulfate, and then concentrated on a rotary evaporator. 6.36 g of the product Petition 870250087268, dated 09 / 26 / 2025, pp. 83 / 94 72 / 79 crude samples were purified by silica gel column chromatography (eluent: hexane: ethyl acetate = gradient from 100:0 to 85:15) to obtain 4.90 g of compound 27 (13.8 mmoles, 92% yield). The XH-NMR data of the obtained compound 27 are presented below.

[177] 1H-NMR (400 MHz, CDCI3, TMS as internal standard) : δ 8.44 (br s, 1 H), 8.03 (br s, 1 H) , 7.90-7.85 (m, 2 H) , 7.54 (tt, J = 7.3, 1.7 Hz, 1 H), 7.50-7.45 (m, 2 H) , 7.08-7.01 (m, 2 H) , 3.50-3.35 (m, 4 H), 3.01-2.88 (m, 1 H), 1.30-1.17 (m, 12 H). Example 15 Synthesis of compound 28

[178] Compound 28 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 85} (Compound 28) ambient temperature

[179] 3.01 g of compound 27 (8.50 mmoles, 1 eq), 45 mL of tetrahydrofuran (dehydrated) and 5 mL of N,N'-dimethylformamide (dehydrated) were added to a three-necked flask of 300 mL, dried in an oven containing a heated magnetic stirring bar in a nitrogen atmosphere. After cooling the reaction solution in an ice bath, 0.48 g of sodium hydride (55% liquid paraffin dispersion, 11.1 mmol, 1.3 eq) was added slowly. After 30 minutes of Petition 870250087268, dated 09 / 26 / 2025, pages 84 / 94 73 / 79 stirring, 0.63 mL of iodomethane (10.2 mmol, 1.2 eq) was added slowly dropwise. The reaction solution was heated slowly to room temperature and stirred for a further 23 hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 10 mL of water were added slowly, and the reaction solution was stirred at room temperature. Water and ethyl acetate were added, and extraction was performed three times with ethyl acetate. The combined organic layer was washed three times with water and once with brine, dried over sodium sulfate, and then concentrated in a rotary evaporator. 3.43 g of the crude product obtained were purified by silica gel column chromatography (eluent: hexane: ethyl acetate = gradient 90:10 to 75:25) to obtain 2.76 g of compound 28 (7.49 mmol, 88% yield). The XH-NMR data for compound 28 obtained are presented below.

[180] xH-NMR (400 MHz, CDCl3, TMS as internal standard): δ 7.35 (br d, J = 7.3 Hz, 2 H), 7.24-7.09 (m, 3 H), 7.02 (br s, 2 H), 6.80 (br s, 1 H), 3.51-3.29 (m, 7 H), 2.79-2.65 (m, 1 H), 1,311.15 (m, 6 H), 1.11-0.96 (m, 6 H). Example 16 Synthesis of compound 29

[181] Compound 29 shown below was synthesized by a The method described below is a reaction. {Chemistry 87} HO NO2 (Compound 29) {Chemistry 88} ____ HNO3 _ )~ Et2O / H2O^ HO Hi according to the following formula of O NO2 Petition 870250087268, dated 09 / 26 / 2025, pages 85 / 94 74 / 79

[182] 75.0 g of 2,5-dimethylphenol, 950 mL of ethyl ether, and 950 mL of water were placed in a 3 L three-necked flask, dried in an oven containing a heated magnetic stirring bar in a nitrogen atmosphere, and cooled in an ice bath under stirring. Then, 79.8 g of fuming nitric acid (97%) were added dropwise over one hour, maintaining the internal temperature at 4.8 °C or less. After the dropwise addition, the solution was stirred for 30 minutes, and then the reaction solution was extracted with ethyl ether. The combined organic layer was washed with water and brine once, dried over magnesium sulfate, and concentrated in a rotary evaporator to obtain 96.7 g of the crude product. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and ethyl acetate in a 4:1 ratio) to obtain 25.8 g (25% yield, reddish-yellow solid) of compound 29. Synthesis of compound 30

[183] ​​Compound 30 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 89} (Compound 30) “L / ΙΝΓΊ2 {Chemistry 90} ______ Pd / C, H2______ ) \ EtOH ) \ HO NO2HO NH2

[184] 25.8 g of compound 29 (155.2 mmol), 1014 ml of ethanol and 136.6 mg of 10% Pd / C (55% water) were placed in a 3 L three-necked flask, dried in an oven, containing a heated magnetic stirring bar. A hydrogen balloon was connected to the flask, the internal atmosphere was replaced with hydrogen three times, the solution was stirred at room temperature for three hours, the hydrogen balloon Petition 870250087268, dated 09 / 26 / 2025, pages 86 / 94 75 / 79 was replaced, the interior was refilled with a hydrogen atmosphere, and the solution was stirred at room temperature for three hours. Then, the reaction solution was filtered with zeolite and washed with ethanol. The filtrate obtained was concentrated in a rotary evaporator to obtain 20.89 g of the crude product. A solid was obtained by purifying the crude product by silica gel column chromatography (using a mixed solvent of dichloromethane and methanol as an eluent, dichloromethane:methanol = gradient from 1:0 to 19:1) and then the concentration of the crude product was washed with toluene at 45 °C and dried to obtain 16.76 g of compound 30 with a yield of 79%. Synthesis of compound 31

[185] Compound 31 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 91}

[186] 3.43 g of compound 30 (25.0 mmol, 1 eq) and 100 mL of chloroform (dehydrated) were added to a 500 mL three-necked flask, dried in an oven, containing a heated magnetic stir bar in a nitrogen atmosphere. Then, 2.22 mL of pyridine (dehydrated, 27.5 mmol, 1.1 eq) were added slowly dropwise at room temperature. After cooling the reaction solution in an ice bath, 3.07 mL of benzoyl chloride (26.3 mmol, 1.05 eq) were added slowly dropwise. After the addition was complete Petition 870250087268, dated 09 / 26 / 2025, pages 87 / 94 76 / 79 drop by drop, the reaction solution was heated to room temperature and stirred for 4.5 hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 10 mL of methanol were added, and the reaction solution was stirred. The reaction solution was filtered by adding water and dichloromethane to obtain compound 31 as a solid. The filtrate was concentrated in a rotary evaporator and filtered again by adding dichloromethane to obtain compound 31 as a solid. Furthermore, the same operation was repeated, and the resulting solid was collected to obtain 5.73 g (23.8 mmol, 95% yield) of compound 31. The XH-NMR data of the obtained compound 31 are presented below.

[187] 1H-NMR (400 MHz, CDCl3, TMS as internal standard): δ 8.44 (s, 1 H), 7.95-7.90 (m, 2 H), 7.82 (br s, 1 H), 7.61 (tt, J = 7.4, 1.6 Hz, 1 H), 7.57-7.50 (m, 2H), 7.00 (d, J = 7.6 Hz, 1H), 6.72 (d, J = 7.6 Hz, 1H), 2.34 (s, 3H), 2.30 (s, 3H). Synthesis of compound 32

[188] Compound 32 shown below was synthesized by a method described below, according to the following reaction formula.

[189] 5.72 g of compound 31 (23.7 mmoles, 1 eq) and 130 mL of pyridine (dehydrated) were added to a 300 mL three-necked flask, dried in an oven, containing a heated magnetic stir bar in a nitrogen atmosphere. In Petition 870250087268, dated 09 / 26 / 2025, pages 88 / 94 77 / 79. Subsequently, 7.51 mL of diethylcarbamoyl chloride (59.3 mmoles, 2.5 eq) were added slowly dropwise at room temperature, and the solution was refluxed for 24 hours. After the reaction was complete, the reaction solution was cooled in an ice bath, 30 mL of water were added slowly, and the reaction solution was stirred at room temperature. Then, the reaction solution was concentrated in a rotary evaporator, where water and ethyl acetate were added, and the reaction solution was extracted with ethyl acetate three times. The combined organic layer was washed with water three times and with brine once, dried over sodium sulfate, and then concentrated in a rotary evaporator. 8.17 g of the crude product obtained were purified by silica gel column chromatography (hexane and dichloromethane were used as an eluent, hexane:dichloromethane = gradient from 100:0 to 70:30) to obtain 4.03 g of compound 32 (11.8 mmoles, 50% yield).The XH—NMR data for compound 32 obtained are presented below. 190 Hz, 2H), 3.41-3.29 (m, 4H), 2.28 (s, 3H), 2.23 (s, 3H), 1.16-0.99 (m, 6H). Example 17 Synthesis of compound 33

[191] Compound 33 shown below was synthesized by a method described below, according to the following reaction formula. {Chemistry 95} (Compound 33) Petition 870250087268, dated 09 / 26 / 2025, pages 89 / 94 78 / 79 {Chemistry 96} OO ambient temperature O O

[192] 4.02 g of compound 32 (11.8 mmol, 1 eq), 60 mL of tetrahydrofuran (dehydrated), and 6 mL of N,N'-dimethylformamide (dehydrated) were added to a 300 mL three-necked flask, dried in an oven, containing a heated magnetic stirring bar in a nitrogen atmosphere. After cooling the reaction solution in an ice bath, 0.67 g of sodium hydride (55%, liquid paraffin dispersion, 15.3 mmol, 1.3 eq) was added slowly. After 30 minutes of stirring, 0.88 mL of iodomethane (14.2 mmol, 1.2 eq) was added slowly dropwise. The reaction solution was heated slowly to room temperature and stirred for a further five hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, 10 mL of water were added slowly, and the reaction solution was stirred at room temperature. Water and ethyl acetate were added, and the extraction was performed three times with ethyl acetate.The combined organic layer was washed three times with water and once with brine, dried over sodium sulfate, and then concentrated in a rotary evaporator. 4.45 g of the crude product obtained were purified by silica gel column chromatography (eluent: hexane: ethyl acetate = gradient from 90:0 to 70:30), and recrystallized with methanol to obtain 3.24 g of compound 33 (9.14 mmoles, 78% yield). The XH-NMR data of the obtained compound 33 are shown below. (Two types of rotamers are generated, each denoted as a major component or a minor component. The ratio between them is major:minor = 92:8.)

[193] XH-NMR (400 MHz, CDCI3, TMS as internal standard): Main component: δ 7.35 (br s, 2 H), 7.25-7.20 (m, 1 Petition 870250087268, dated 09 / 26 / 2025, pp. 90 / 94 79 / 79 H), 7.17-7.10 (m, 2 H), 6.99 (br d, J = 7.8 Hz, 1 H), 6.87 (br d, J = 7.8 Hz, 1 H), 3, 64-3, 22 (m, 7 H), 2.26-1, 99 (m, 6 H-1, 3, 15 H).

[194] Secondary component: δ 7.55-7.50 (m, 2 H), 7.46-7.41 (m, 3 H), 7.17-7.10 (m, 1 H), 7.07 (br d, J =8.0 Hz, 1 H), 3.643.2, (s, 3 H), (s, 3 H 2.30 (s, 3 H), 2.26-1.99 (m, 3 H), 1.33-1.15 (m, 6 H). Petition 870250087268, of 26 / 09 / 2025, p. 91 / 94

Claims

1 / 2 CLAIMS 1. Carbamate compound characterized in that it is represented by the following formula (0): {Chemistry 1} (0) wherein 1 is 0 or 1, m is an integer from 1 to 4, n is an integer from 1 to 4, R1 and R2 are each a substituent with an R10CR2- structure, R3 is a hydrogen atom or a substituent with an R10-CR2- structure, R4 is a substituent selected from a substituent with an R10-CR2- structure, a substituent with an R10At16- structure, and a substituent with an R102-At15- structure, At15 is an atom of Group 15 in the periodic table, and At16 is an atom of Group 16 in the periodic table, R and R10 are each a group containing an atom selected from carbon, hydrogen, and elements of Groups 15, 16 and 17 From the periodic table, which have 0 to 17 carbon atoms and 0 to 4 atoms of elements from Groups 15, 16, and 17 of the periodic table, R1 to R4 and R can bond to form a monocyclic ring. Petition 870250087268, dated 09 / 26 / 2025, pages 92 / 94 2 / 2 or polycyclic, and a plurality of R and R10 can link to form a monocyclic or polycyclic ring or form a multiple bond.

2. Carbamate compound according to claim 1, characterized in that the compound is represented by the following formula (1): {Chemistry 2} (D where n is an integer from 2 to 4, in, R1, R2, R3, R4, and R have the same meaning as m, R1, R2, R3, R4, and R in formula (0).

3. Carbamate compound according to claim 1 or 2, characterized in that R3 is a substituent with an R10-CR2- structure.

4. Carbamate compound according to claim 1 or 2, characterized in that R4 is a substituent with an R10-CR2- structure.

5. Carbamate compound according to claim 1 or 2, characterized in that At15 is a nitrogen atom.

6. Carbamate compound according to claim 1 or 2, characterized in that At16 is an oxygen atom. Petition 870250087268, dated 09 / 26 / 2025, pp. 93 / 94