Cyclopropanecarbonyl chloride → 3-(1-cyanocyclopropyl)-N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methoxyphenyl]benzamide

Participants

Reaction Steps

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methoxyphenyl}-3-(1-cyanocyclopropyl)benzamide (528.0 mg, 1.15 mmol) in pyridine (10 mL) were added N,N-dimethylpyridine-4-amine (52.1 mg, 426 μmol) and cyclopropanecarbonyl chloride (1 mL, 11.0 mmol), and the mixture was stirred at room temperature for 6 hr. The reaction solution was concentrated under reduced pressure, and the residue was diluted with ethyl acetate (50 mL), washed with water (50 mL), 0.1N hydrochloric acid (50 mL) and saturated aqueous sodium hydrogen carbonate solution (50 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate/hexane=5/95→80/20) and recrystallized from acetone to give the title compound (280 mg, 46%) as colorless crystals.

Provenance & Evidence