Water → 3-(1-cyano-1-methylethyl)-N-[3-({2-[(hydroxyacetyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]benzamide

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Reaction Steps

To a solution of N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide (219 mg, 0.531 mmol) in pyridine (10 mL) was added 2-chloro-2-oxoethyl acetate (171 μL, 1.59 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in methanol (10 mL). Potassium carbonate (147 mg, 1.06 mmol) was added thereto, and the mixture was stirred at room temperature for 19 hr. Water (30 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50 mL, 2×10 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→90/10), and fractions containing the desired product were concentrated under reduced pressure. Ethyl acetate and diisopropyl ether were added to the obtained residue. The obtained precipitate was collected by filtration, and dried to give the title compound (140 mg, 56%) as a pale-yellow powder.

Provenance & Evidence