Cyclopropanecarbonyl chloride → Tert-butyl [2-chloro-5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamate

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To a solution of tert-butyl {5-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-2-chlorophenyl}carbamate (5.49 g, 14.60 mmol) in N,N-dimethylacetamide (40 mL) was added cyclopropanecarbonyl chloride (1.50 mL, 16.5 mmol) at 0° C., and the mixture was stirred at room temperature for 14 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate-hexane to give the title compound (5.61 g, 87%) as a white solid.

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