2,3,5-substituted imidazole[1,2-c]-thiophene[2,3-e]-7(8H)keto heterocyclic compound and synthetic method thereof

A technology for a heterocyclic compound and a synthesis method, which is applied in the fields of organic compound synthesis and medicine, can solve the problems of high yield and few steps, and achieve the effects of high yield, moderate reaction time, and high product purity and yield.

Active Publication Date: 2016-05-04
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

The synthesis method has few steps, high yield, low toxicity (does not contain reagents such as phosphorus) and is easy to operate, and overcomes the shortcomings in the existing similar heterocyclic compound synthesis methods

Method used

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  • 2,3,5-substituted imidazole[1,2-c]-thiophene[2,3-e]-7(8H)keto heterocyclic compound and synthetic method thereof
  • 2,3,5-substituted imidazole[1,2-c]-thiophene[2,3-e]-7(8H)keto heterocyclic compound and synthetic method thereof
  • 2,3,5-substituted imidazole[1,2-c]-thiophene[2,3-e]-7(8H)keto heterocyclic compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Synthesis of 2,3,5-substituted imidazo[1,2-c]-thien[2,3-e]pyrimidin-7(8H)one heterocyclic compound

[0044] (1) Add 43.6 grams (0.2 moles) of 3-amino-5-(4-fluorophenyl)thiophene-2-carbonitrile and N,N-dimethylformamide dimethyl to a 100 ml single-necked round bottom flask base acetal 50 grams. Then a mixed solvent of toluene and acetonitrile was added (the volume ratio of toluene and acetonitrile in the mixed solvent 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 Dimethylformimidamide [(E)-N'-(2-cyano-5-(4-fluorophenyl)thiophen-3-yl)-N,N-dimethylformimidamide] 53.2 g, yield 97%.

[0045] 1 HNMR (DMSO d6 )300MHz(ppm):...

Embodiment 2

[0050] Example 2: Synthesis of 2,3,5-substituted imidazo[1,2-c]-thien[2,3-e]pyrimidin-7(8H)one heterocyclic compound

[0051] (1) Add 21.8 g (0.1 mol) of 3-amino-5-(4-fluorophenyl)thiophene-2-carbonitrile and N,N-dimethylformamide dimethylformamide to a 100 ml single-necked round bottom flask base acetal 40 grams. The reaction mixture was stirred overnight at room temperature. TLC and HPLC analysis indicated the reaction was complete. Rotary steaming and recovery of N,N-dimethylformamide dimethyl acetal. The residue was washed with cold diethyl ether (2x5 mL), then dried in vacuo to give pure pale yellow intermediate (E)-N'-(2-carbonitrile-5-(4-fluorophenylthiophene)-3-N, N-dimethylformimidamide [(E)-N'-(2-cyano-5-(4-fluorophenyl)thiophen-3-yl)-N,N-dimethylformimidamide] 24.1 g, yield 88%.

[0052] (2) Add 13.7 grams of (E)-N'-(2-carbonitrile-5-(4-fluorophenylthiophene)-3-N,N-dimethylmethylamide into a 50 ml single-necked round bottom flask (0.05 mole) and glycine ethyl e...

Embodiment 3

[0053] Example 3: Synthesis of 2,3,5-substituted imidazo[1,2-c]-thien[2,3-e]pyrimidin-7(8H)one heterocyclic compound

[0054] (1) Add 87.3 grams (0.4 moles) of 3-amino-5-(4-fluorophenyl)thiophene-2-carbonitrile and N,N-dimethylformamide dimethylformamide to a 500 ml single-necked round bottom flask base acetal 100 g. Then 200 ml of acetonitrile was added, and the reaction mixture was stirred overnight at 70°C. TLC and HPLC analysis indicated the reaction was complete. Acetonitrile and N,N-dimethylformamide dimethyl acetal were removed by rotary evaporation. The residue was washed with petroleum ether, and then dried in vacuo to obtain a light yellow intermediate (E)-N'-(2-carbonitrile-5-(4-fluorophenylthiophene)-3-N,N-dimethylmethylamide 【(E)-N'-(2-cyano-5-(4-fluorophenyl)thiophen-3-yl)-N,N-dimethylformimidamide】98.3 g, yield 90%.

[0055] (2) Add 41 grams of (E)-N'-(2-carbonitrile-5-(4-fluorophenylthiophene)-3-N,N-dimethylmethylamide into a 250 ml single-necked round bott...

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Abstract

The invention discloses a 2,3,5-substituted imidazole[1,2-c]-thiophene[2,3-e]-7(8H)keto heterocyclic compound of which the structure is shown as a formula (I) shown in the description. The invention also discloses a preparation method of the compound and application of the compound in preparing antineoplastic drugs. The 2,3,5-substituted imidazole[1,2-c]-thiophene[2,3-e]-7(8H)keto heterocyclic compound provided by the invention adopts a two-step synthesis method, a one-pot reaction is adopted for forming two heterocyclic rings, the reaction material is easily obtained, the operation is convenient, the reaction condition is mild, the reaction time is moderate, the control is easy, the after-treatment is simple, the purity and yield of a product are high, and the compound and the synthetic method thereof have the advantages of being less in operation step, high in yield, free of reagents such as phosphorus, low in toxicity, convenient to operate and the like.

Description

technical field [0001] The invention relates to a 2,3,5-position substituted imidazo[1,2-c]-thiophene[2,3-e]pyrimidin-7(8H)one heterocyclic compound and a synthesis method thereof, belonging to the synthesis of organic compounds and medical technology. 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. Heterocyclic compounds are more and more widely used in antitumor and cardiovascular drugs, antibacterial drugs and chemotherapy, chemiluminescent materials, conductive polymers, dyes with new structures, and fused heterocyclic flavors. Some heterocyclic compounds have strong anti-tumor activity and have attracted widespread attention (see structures I, II, III below). [0003] [0004] Documents International Journal of...

Claims

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Application Information

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