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Intermediate of telmisartan, its preparation and use

A technology for telmisartan and an intermediate, which is applied in the field of preparing telmisartan, can solve the problems of short reaction time, little environmental pollution, serious environmental pollution and the like, and achieves the advantages of industrial production, little environmental pollution and safe operation. Effect

Active Publication Date: 2007-08-29
ZHEJIANG MENOVO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to solve the deficiencies such as low preparation yield, long reaction time and serious environmental pollution of telmisartan in the prior art, the invention provides a new intermediate for preparing telmisartan and its preparation, and A kind of preparation method of telmisartan with high yield, short reaction time and little environmental pollution

Method used

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  • Intermediate of telmisartan, its preparation and use
  • Intermediate of telmisartan, its preparation and use
  • Intermediate of telmisartan, its preparation and use

Examples

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Embodiment 1

[0038] Example 1: Preparation of 7-methyl-2-propyl-3H-benzimidazole-5-formyl chloride

[0039] Add 11g of 7-methyl-2-propyl-3H-benzimidazole-5-carboxylic acid, 100ml of thionyl chloride and 1ml of DMF into a 250ml three-necked flask, heat and reflux under stirring for half an hour, and recover the excess chloride under reduced pressure. Add 100ml of toluene to sulfoxide, stir and suction filter until dry to obtain 7-methyl-2-propyl-3H-benzimidazole-5-carbonyl chloride, which is directly used in the next step.

Embodiment 2

[0040] Example 2: Preparation of 7-methyl-N-(2-(methylamino)phenyl)-2-n-propyl-3H-benzimidazole-5-carboxamide

[0041] Add 9.5 g of N-methyl o-phenylenediamine hydrochloride and 300 ml of dichloromethane into a 500 ml three-necked flask, stir and cool to 0-5°C, then add the benzimidazole chloride obtained in the previous step. Add triethylamine dropwise while keeping warm, continue to stir for half an hour after the dropwise addition is completed, filter the reaction solution with suction, concentrate the filtrate to dryness, dissolve the residue in 300ml of 5% dilute hydrochloric acid, and dissolve it with 5% sodium hydroxide solution under stirring. The pH value of the solution was adjusted to 11, a white solid was precipitated, filtered with suction, the filter cake was washed with water to neutrality, and dried under an infrared lamp to constant weight to obtain 7-methyl-N-(2-(methylamino)phenyl)- 2-n-propyl-3H-benzimidazole-5-carboxamide, the yield is 83%.

Embodiment 3

[0042] Example 3: 4'-((4-methyl-6-(2-methylamino)phenylcarbamoyl)-2-n-propyl-1H-benzimidazol-1-yl)methyl)biphenyl - Preparation of methyl 2-carboxylate

[0043] Add 7-methyl-N-(2-(methylamino)phenyl)-2-n-propyl-3H-benzimidazole-5-carboxamide 10g, 300ml acetonitrile in a 500ml three-necked flask protected by nitrogen, Stir and cool to between 0 and 5°C, add 4g of sodium hydride and stir for 10 minutes, add 9g of 4'-bromomethylbiphenyl-2-benzyl carboxylate in batches under heat preservation, continue stirring for half an hour after the addition, the reaction solution Pour into 500ml of water, extract the aqueous phase with dichloromethane, combine the dichloromethane layers, and concentrate to dryness to give 4'-((4-methyl-6-(2-methylamino)phenylcarbamoyl)-2- n-Propyl-1H-benzimidazol-1-yl)methyl)biphenyl-2-carboxylic acid methyl ester. Yield 62%.

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Abstract

The invention supplies an intermediate to make intermediate of Telmisartan that has the structure of 4'-((4- methyl-6-(2- methylamino) carbanilino)-2-propyl-1H- benzimidazole-1-radicle) methyl) biphenyl-2-carboxylic acid. It has the advantages of high yield, save operation, low environment pollution, etc.

Description

(1) Technical field [0001] The present invention relates to a new intermediate for the preparation of telmisartan: 4'-((4-methyl-6-(2-methylamino)phenylcarbamoyl)-2-n-propyl-1H- Benzimidazol-1-yl)methyl)biphenyl-2-carboxylic acid, its preparation method and its application in the preparation of telmisartan. (2) Background technology [0002] Telmisartan (telmisartan) is a new type of non-peptide angiotensin II (AT II) receptor antagonist, which has the characteristics of high efficiency, small dose, long action time and low toxicity for hypertension. It was first listed in the United States by Boehringer Ingelheim in 1999 under the trade name Micardis. [0003] The chemical name of Telmisartan is: 4'-(4-methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-n-propyl-1H-benzimidazol-1 -yl) methyl) biphenyl-2-carboxylic acid, the structural formula is as follows: [0004] [0005] The synthetic route (Scheme1) that document J.Med.Chem.1993,36,4040-4051 reports is that compound 7-met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/08
Inventor 唐朝军陈为人
Owner ZHEJIANG MENOVO PHARMA
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