Oxalyl chloride → N-{6-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy][1,2,4]triazolo[1,5-a]pyridin-2-yl}-1,3-oxazole-4-carboxamide

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Reaction Steps

To a solution of 1,3-oxazole-4-carboxylic acid (145 mg, 1.29 mmol) in tetrahydrofuran (3 mL) were added oxalyl chloride (157 μL, 1.80 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 the above-mentioned N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide (213 mg, 516 μmol) were dissolved in pyridine (8 mL), and the mixture was stirred at room temperature for 25 hr. A saturated aqueous sodium hydrogen carbonate solution (10 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 mL, 2×10 mL). The combined organic layer was washed with saturated brine (5 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→97/3), and fractions containing the desired product were concentrated under reduced pressure. Diisopropyl ether was added to the obtained residue. The obtained precipitate was collected by filtration and dried to give the title compound (211 mg, 81%) as a colorless powder.

Provenance & Evidence