Oxalyl chloride → HCID 57749247, compound

Participants

Reaction Steps

To a solution of 6-methylpyridine-3-carboxylic acid (252 mg, 1.84 mmol) in tetrahydrofuran (6 mL) were added oxalyl chloride (200 μL, 2.30 mmol) and N,N-dimethylformamide (20 μL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure. The obtained residue and N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (196 mg, 0.460 mmol) were dissolved in pyridine (7 mL), and the mixture was stirred at room temperature for 7 days. A saturated aqueous sodium hydrogen carbonate solution (20 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (30 mL, 10 mL). The combined organic layer was washed with saturated brine (10 mL) and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/methanol=100/0→99.5/0.5), and fractions containing the desired product were concentrated under reduced pressure. The obtained residue was recrystallized from methanol to give the title compound (124 mg, 49%) as colorless crystals.

Provenance & Evidence