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Method for preparation of benzimidazole derivatives

一种苯并咪唑、衍生物的技术，应用在制备苯并咪唑衍生物领域，能够解决暴露等问题，达到优良制造收率的效果

Active Publication Date: 2016-03-02
HK INNO N CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction requires an additional reactor and there is a risk of exposure to carbon monoxide during the process

Method used

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  • Method for preparation of benzimidazole derivatives
  • Method for preparation of benzimidazole derivatives
  • Method for preparation of benzimidazole derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0089] Embodiment 1: step a

Embodiment 1-1

[0090] 1) embodiment 1-1: the preparation of acetimidic acid methyl ester hydrochloride

[0091] 1.6 kg of acetonitrile and 2.4 kg of methanol were added to the reactor and the reactor was cooled to -10°C. Acetyl chloride in an amount of 3.67 kg was slowly added thereto and the mixture was stirred at 0°C for 12 hours. While stirring, the internal temperature of the reactor was maintained at 0°C. At the end of the reaction, the solvent was removed under reduced pressure at 45°C. 11.8 kg of tert-butyl methyl ether were added to the reaction mixture and the mixture was stirred at 0°C for 3 hours. The resulting solid was filtered and vacuum-dried at 40° C. to obtain 4.1 kg of methyl acetimidic acid hydrochloride (yield: 95%).

[0092] 1 H-NMR (400MHz, DMSO-d 6 ): 11.7(s, 2H), 4.07(s, 3H), 2.38(s, 3H)

Embodiment 1-2

[0093] 2) embodiment 1-2: the preparation of acetimidic acid ethyl ester hydrochloride

[0094] 1.6 kg of acetonitrile and 4.3 kg of ethanol were added to the reactor and the reactor was cooled to -10°C. Acetyl chloride in an amount of 3.67 kg was slowly added thereto and the mixture was stirred at 0°C for 12 hours. While stirring, the internal temperature of the reactor was maintained at 0°C. At the end of the reaction, the solvent was removed under reduced pressure at 45°C. 11.8 kg of tert-butyl methyl ether were added to the reaction mixture and the mixture was stirred at 0°C for 3 hours. The resulting solid was filtered and vacuum-dried at 40° C. to obtain 4.58 kg of ethyl acetimidate hydrochloride (yield: 95%).

[0095] 1 H-NMR (400MHz, DMSO-d 6 ): 11.7(s, 2H), 4.26(q, 2H), 2.38(s, 3H), 1.36(t, 3H)

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Abstract

The present invention provides a method for preparing a compound with a benzimidazole structure with an excellent yield using a low-cost starting material, not requiring an additional separation process, or not using a dangerous reagent during the manufacturing process. Furthermore, the present invention also provides an intermediate and a final product produced by the preparing method.

Description

technical field [0001] The present invention relates to a process for the preparation of benzimidazole derivatives. Background technique [0002] Benzimidazoles are known to be very important pharmacophores in the fields of medicine and chemistry. In terms of chemical structure, the compound has a condensed form between a benzene ring and an imidazole ring, and has various medicinal properties. In the 1990's, a number of benzimidazole derivatives with substituents such as fluorine and propylene were synthesized and shown to have stability, bioavailability and biological activity. [0003] Recently, with the extremely high prevalence of drug-resistant bacteria, compounds having a benzimidazole structure have been used as chemotherapeutic agents for treating drug-resistant bacteria infections. This is due to the ability of benzimidazoles to inhibit bacterial nucleic acid and protein synthesis due to their structural similarity to purines. Oxidazol-1H-benzimidazole, as a rep...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/08A61K31/4184A61P1/04
CPCA61P1/04A61P31/00C07D235/08A61K31/4184
Inventor 权在洪金银仙宋硕范李圣雅李枝润崔光道朴映准
Owner HK INNO N CORP
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