Ammonia → 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 5.1 g of methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thio-phene-2-carboxylate and 500 ml of a 7 N solution of ammonia in methanol is stirred in an autoclave at 125° C. for 4 hours. The mixture is allowed to cool down to room temperature and concentrated to dryness. During the reaction the TBDMS group of the title product is partially removed. The crude is purified by flash chromatography [silica gel, eluent: cyclohexane/ethyl acetate/methanol, elution gradient of 40/60/0 (v/v/v) to 0/100/0 (v/v/v) and then to 0/90/10 (v/v)] to give the title compound. Additionally, 5-[6-(hydroxymethyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide is obtained.

Provenance & Evidence