methyl 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate → 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate (310 mg, 0.69 mmol) in 2N LiOH (15 mL) and THF (15 mL) was stirred at 50° C. for 8 h. It was cooled to room temperature and the precipitate was collected by filtration. It was then poured into water (50 mL) and the suspension was acidified with formic acid to pH=1. It was filtered and the solid was purified by chromatography on silica gel eluted with MeOH/DCM=1/5 to afford the desired product as a gray solid (184 mg, 61%); LC/MS: MS (ES+) m/e 435 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.54 (s, 3H), 2.79 (s, 3H), 3.51 (s, 4H), 3.67 (s, 4H), 5.67 (s, 2H), 7.20 (d, J=10.2 Hz, 1H), 7.35 (t, J=7.8 Hz, 1H), 7.42 (s, 1H), 7.69 (d, J=10.2 Hz, 1H).

Provenance & Evidence