1-Methylpiperazine → 5-{6-[(4-methylpiperazin-1-yl)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 3.6 g of [1-(5-carbamoyl-4-{(1R)-1-[2-(trifluoro-methyl)phenyl]ethoxy}-2-thienyl)-1H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate and 3.7 ml of 1-methylpiperazine in 80 ml dichloromethane is stirred at 40° C. for 2 hours. The reaction mixture is concentrated to dryness and the resulting residue is purified by flash chromatography [silica gel, eluent: dichloromethane/methanol/triethylamine, elution gradient 99.7/0/0.3 (v/v/v) to 89.7/10/0.3 (v/v/v)]. The obtained product is filtered through a short plug of Flash-NH2 silica gel [eluent: dichloro-methane/methanol, 9/1 (v/v)] in a further purification step. After evaporation of the solvents, the resulting oil is treated with 5 ml diethyl ether, resulting in precipitation of the product. After filtration the title compound is obtained as white solid.

Provenance & Evidence