Ammonia → 5-[6-(aminomethyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 150 mg of crude [3-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-3H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate (example 49, step 1) in 5 ml of a saturated solution of ammonia in methanol is stirred in a microwave vial at 80° C. for 1 h in the microwave cavity. The solvent is removed under reduced pressure. 20 ml of water and 20 ml dichloromethane is added to the residue, the organic phase is separated and the aqueous phase is extracted with 2×10 ml dichloromethane. The combined organic layers are dried over MgSO4, filtered and evaporated under reduced pressure. The resulting residue is purified by flash chromatography [silica gel, eluent: dichloromethane/methanol/7 N solution of ammonia in methanol, 9/1/0.3 (v/v/v)] to yield the title product.

Provenance & Evidence