Cyclopropylamine → HCID 57749171, compound

Participants

Reaction Steps

To a solution of N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide (129 mg, 0.359 mmol) and N,N-diisopropylethylamine (184 μL, 1.075 mmol) in tetrahydrofuran (5 mL) was added 2,2,2-trichloroethyl chlorocarbonate (52.0 μL, 0.378 mmol), and the mixture was stirred at room temperature for 30 min. Cyclopropaneamine (150 μL, 2.17 mmol) and N,N-dimethylacetamide (5 mL) were added to the reaction mixture, and the mixture was stirred at 80° C. for 22 hr. The reaction mixture was concentrated under reduced pressure, diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with 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 purified by silica gel column chromatography (0%→100% ethyl acetate-hexane) to give the title compound (20.3 mg, 13%) as a white solid.

Provenance & Evidence