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Reprocessing of 2-propyl-4-methyl-(methylbenzaimidazole - 2-yl) – benzimidazole and preparation of 4’-(2-Propyl-4-methyl-6-(metylbenzimidazoyl-2-yl)benzimidazol-1-ylmethyl)biphenyl-2- carboxylic acid Disclosure Number: IPCOM000125171D
Publication Date: 2005-May-23
Document File: 2 page(s) / 63K

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Reprocessing of 2-propyl-4-methyl-(methylbenzaimidazole - 2-yl) - benzimidazole and preparation of 4'-(2-Propyl-4-methyl-6- (metylbenzimidazoyl-2-yl)benzimidazol-1-ylmethyl)biphenyl-2- carboxylic acid

Preparation of 2-propyl-4-methyl-(methylbenzaimidazole-2-yl)-benzimidazole:

    The process for reprocessing 2-propyl-4-methyl-(methylbenzaimidazole-2-yl)- benzimidazole (BIM) comprises: mixing, while stirring at an elevated temperature, BIM with IPA to obtain a solution, adding acetic acid and water, heating the reaction mixture to a temperature of about 25ºC to about 65ºC, adding a base, preferably NaOH, cooling the reaction mixture, and isolating the BIM. Preferably, the elevated temperature is about 50°C. Preferably, further to the stirring at elevated temperature, the reaction mixture is hot filtered over Hyflo. Preferably the reaction mixture is heated to about 65oC. Preferably, the reaction mixture is cooled to a temperature to less than about 25oC, more preferably to a temperature of about 5oC.

Preparation of 4'-(2-Propyl-4-methyl-6-(metylbenzimidazoyl-2-yl)benzimidazol-1- ylmethyl)biphenyl-2-carboxylic acid:

    The process for preparing 4'-(2-Propyl-4-methyl-6-(metylbenzimidazoyl-2- yl)benzimidazol-1-ylmethyl)biphenyl-2-carboxylic acid (TLM) comprises two steps:
1) compression step: mixing BIM, 4'-bromomethyl-(1,1'-biphenyl)-2-carboxylate methyl ester (BMB) and at least 1eq. of a base, stirring the reaction mixture, adding acetone to form TLM- OMe, and removing preferably by distullation, the acetone until obtaining dry TLM-OMe
2) Hydrolysis of the methyl ester group of TLM-OMe: adding a C1-C2 alcohol and a base to the reaction mixture, heating the reaction mixture to reflux unti...