Triethylamine → HCID 58158495, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of bis(trichloromethyl) carbonate (127 mg, 0.43 mmol) in tetrahydrofuran (4 mL) were slowly added a solution of 3-(4-fluorophenyl)-4-methyl-5,6-dihydropyridin-2(1H)-one (240 mg, 1.2 mmol) and triethylamine (240 mg, 2.3 mmol) in tetrahydrofuran (2 mL) under ice-cooling, and the mixture was stirred at 0° C. for 40 min and at room temperature for 15 min. A solution of N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (250 mg, 0.78 mmol) in tetrahydrofuran (4 mL) and triethylamine (79 mg, 0.78 mmol) were added to the mixture, and the mixture was stirred at room temperature for 2 hr. Ethyl acetate/tetrahydrofuran and saturated brine were added to the mixture, and the aqueous layer was extracted 3 times with ethyl acetate/tetrahydrofuran. The combined 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 purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=40/60→90/10) to give the title compound (170 mg, 39%) as a white solid.

Provenance & Evidence