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Preparation method of 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-dicarboxylic acid ester

A dicarboxylate, diazepine technology applied in 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4] In the field of diazepine-1,8(9H)-dicarboxylate production method, it can solve the problems of no suitable industrial synthesis method, and achieve the effects of short synthesis route, easy reaction and convenient operation

Inactive Publication Date: 2019-12-13
上海药明康德新药开发有限公司
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Problems solved by technology

Mainly solve the technical problem that there is no suitable industrial synthesis method at present

Method used

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  • Preparation method of 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-dicarboxylic acid ester
  • Preparation method of 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-dicarboxylic acid ester

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Embodiment 1

[0010] Embodiment 1: a, compound 5A_2 (212 g, 2.0 mol) and TsOH . h 2 O (5.7 g, 0.03 mol) was dissolved in toluene (1.5 L), 5A_1 (195 g, 2.6 mol) was added, the reaction solution was heated to reflux, and the reaction was continued for 16 hours. The reaction system was cooled to room temperature and distilled under reduced pressure to obtain the crude compound 5A_3 (400 g) as a colorless oil, which was directly used in the next reaction.

[0011] b. The crude compound 5A_3 (400 g) was dissolved in ethanol (1.8 L), and sodium borohydride (114 g, 3.0 mol) was added at 0°C. The reaction was controlled and continued for 17 hours at room temperature (20-30°C). Add water to quench, the reaction solution was distilled under reduced pressure to remove ethanol, and the residue was extracted with ethyl acetate (1000 mL x 3). The combined organic phases were washed with saturated sodium carbonate, the organic phase was dried over sodium sulfate, filtered and concentrated by distillati...

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Abstract

The invention relates to a preparation method of 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-dicarboxylic acid ester. A purpose of the present invention is to mainly solvethe technical problem that no suitable industrial synthesis method exists at present. According to the present invention, the method comprises nine steps, the synthetic route is defined in the specification, and the obtained compound can be used as the useful intermediate or product for synthesizing a plurality of medicines.

Description

technical field [0001] The present invention relates to 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-di Synthesis method of formate ester (CAS: 1094091-81-2). Background technique [0002] 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-dicarboxylate And related derivatives are widely used in medicinal chemistry and organic synthesis. Currently about 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-dicarboxylic acid There are few reports on the synthesis of base esters, and similar literature reactions have certain risks, long routes, and low yields. Therefore, it is necessary to develop a synthetic method with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and suitable overall yield. Contents of the invention [0003] The purpose of this invention is to develop a kind of 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,7-dihydro-5H-imidazo[1, Synthesis of 5-a][1,4]...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 焦家盛任文武周强陈佩张莉莉李贺山安自强何燕平刘月领刘胜攀徐富军杨芳王瑞琪于凌波马汝建
Owner 上海药明康德新药开发有限公司
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