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Imidazo[1,2-c]-thiophene[2,3-e]pyrimidine-7(8h)one heterocyclic compound and synthesis method thereof

A technology of heterocyclic compounds and synthetic methods, applied in the fields of fine organic synthesis and medicinal chemistry, to achieve the effects of high yield, easy operation, and mild reaction conditions

Active Publication Date: 2017-09-29
山东益康药业股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] [1,2-c]-thiophene[2,3-e]pyrimidin-7(8H)one heterocycles (compounds 3 and 5) have not been reported in the literature

Method used

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  • Imidazo[1,2-c]-thiophene[2,3-e]pyrimidine-7(8h)one heterocyclic compound and synthesis method thereof
  • Imidazo[1,2-c]-thiophene[2,3-e]pyrimidine-7(8h)one heterocyclic compound and synthesis method thereof
  • Imidazo[1,2-c]-thiophene[2,3-e]pyrimidine-7(8h)one heterocyclic compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] first step of reaction

[0038] Add 43.6 g (0.2 mol) of 3-amino-5-(4-fluorophenyl)thiophene-2-carbonitrile and 50 g of N,N-dimethylformamide dimethyl acetal into a 100 mL single-necked round bottom flask , and then 20 mL of a mixed solvent of toluene and acetonitrile was added (the volume ratio of toluene and acetonitrile was 1:1), and the reaction mixture was stirred at 70° C. for 8 hours. TLC and HPLC analysis indicated the reaction was complete. The solvent and N,N-dimethylformamide dimethyl acetal were removed by rotary evaporation. The residue was washed with cold diethyl ether, then dried in vacuo to give pure light yellow intermediate (E)-N'-2-carbonitrile-5-(4-fluorophenylthiophene)-3-N,N-dimethyl Methamide [(E)-N'-(2-cyano-5-(4-fluorophenyl)thiophen-3-yl)-N,N-dimethylformimidamide] 53.2 g, yield 97%. 1 H NMR (DMSO d6 )300MHz(ppm):7.88(1H,s),7.80(2H,m),7.61(1H,s),7.41(2H,m),2.96(3H,s),2.99(3H,s); MS: m / z (M+1) 274.11.

[0039] second step of th...

Embodiment 2

[0042] The first step of the reaction is the same as in Example 1.

[0043] React second step:

[0044]Add (E)-N'-2-formonitrile-5-(4-fluorophenylthiophene)-3-N,N-dimethylmethylamide 2.73 g (0.01 mol) and ( R)-2-amino-2-phenylacetic acid ethyl ester hydrochloride 3.24 g (0.015 mol), then add 15 mL of glacial acetic acid. The reaction mixture was heated (100° C.) with stirring for 8 hours. TLC and HPLC followed the reaction. After the reaction was completed, part of the glacial acetic acid was removed by rotary evaporation, and the reacted mixed solution was allowed to stand overnight to obtain

[0045] (R)-2-(-fluorophenyl)-8-phenyl-imidazo[1,2-c]-thiophene[2,3-e]pyrimidin-7(8H)one [(R)-2-( 4-fluorophenyl)-8-phenylimidazo[1,2-c]thieno[2,3-e]pyrimidin-7(8H)-one] 3.1 g of product (light gray crystals), yield 86%.

Embodiment 3

[0047] The first step of the reaction is the same as in Example 1.

[0048] React second step:

[0049] Add (E)-N'-2-carbonitrile-5-(4-fluorophenylthiophene)-3-N,N-dimethylmethylamide 1.37 g (0.005 mol) and ( R)-2.15 g (0.01 mol) of ethyl 2-amino-2-phenylacetate hydrochloride, and then add 10 mL of glacial acetic acid. The reaction mixture was heated (90° C.) with stirring for 12 hours. TLC and HPLC followed the reaction. After the reaction was completed, glacial acetic acid was removed by rotary evaporation, and the residue was subjected to silica gel column chromatography (developing solvent volume ratio of ethyl acetate:n-hexane 1:4) to obtain (R)-2-(-fluorophenyl)-8-phenyl -Imidazol[1,2-c]-thiophene[2,3-e]pyrimidin-7(8H)one[(R)-2-(4-fluorophenyl)-8-phenylimidazo[1,2-c]thieno[ 2,3-e]pyrimidin-7(8H)-one] 1.4 g of product (gray crystals), yield 78%.

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Abstract

The invention discloses an imidazole[1,2-c]-thiophene[2,3-e]pyrimidine-7(8H)ketone heterocyclic compound and a synthesis method thereof, and relates to the field of organic synthesis and medicinal chemistry. The synthesis method includes the following step that a compound 1 and a compound 2 or a compound 4 are reacted in a suitable solvent at the suitable temperature to obtain optically-active (S)-imidazole[1,2-c]-thiophene[2,3-e]pyrimidine-7(8H)ketone heterocyclic compound 3 (in the following general formula) or a fused ring compound 5 (in the following general formula) of a (R)-imidazole[1,2-c]-thiophene[2,3-e]pyrimidine-7(8H)ketone heterocyclic compound. The imidazole[1,2-c]-thiophene[2,3-e]pyrimidine-7(8H)ketone heterocyclic compound and the synthesis method have the advantages that two heterocyclic rings are formed through a one-pot reaction; raw materials are easy to obtain, and the reaction condition is moderate; reaction time is moderate, control is easy, and post-treatment is simple; the product purity and the product yield are high; the environment is not polluted, and the green chemistry concept is fully reflected.

Description

technical field [0001] The invention belongs to the field of fine organic synthesis and medicinal chemistry, and specifically relates to an imidazol[1,2-c]-thiophene[2,3-e]pyrimidin-7(8H)one heterocyclic compound and a synthesis method thereof. Background technique [0002] Heterocyclic compounds widely exist in drug molecules and play a pivotal role in the process of drug synthesis and discovery, because the existence of heterocycles can not only affect the interaction between drug molecules and receptors, but also help improve the solubility. Anti-tumor and cardiovascular drugs, antibacterial drugs and chemotherapy are more and more widely used. Some heterocyclic compounds have been widely concerned due to their strong antitumor activity (see structures I, II, III below). [0003] [0004] The literature International Journal of Research in Pharmacy and Chemistry Volume 4 Issue 3, p501-508, 2014 and Medicinal Chemistry Research Volume 22 Issue 2p 659-673 reported that...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/14A61K31/519A61P35/00A61P9/00
CPCC07D495/14
Inventor 韩迎高肇林史永强郑辉张兴柱魏正风
Owner 山东益康药业股份有限公司
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