Cyclopropanecarbonyl chloride → Benzyl [4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]carbamate

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Reaction Steps

To a solution of benzylcarbamate {4-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}carbamate (8.7 g, 22.2 mmol) in N,N-dimethylacetamide (70 mL) was added cyclopropanecarbonyl chloride (2.21 mL, 24.4 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with hexane/ethyl acetate (=1/1) and collected by filtration to give the title compound (8.5 g, 87%) as a thin-brown solid.

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