Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Participants

Reaction Steps

To a solution of N-[6-(4-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (100 mg, 0.324 mmol) and 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (96.1 mg, 0.389 mmol) in N,N-dimethylformamide (1.0 mL) were added HATU (147.8 mg, 0.389 mmol) and N,N-diisopropylethylamine (111.6 μL, 0.648 mmol), and the mixture was stirred at room temperature for 20 hr. Tetrahydrofuran, ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was washed with tetrahydrofuran and collected by filtration to give the title compound (154 mg, 88%) as a white solid.

Provenance & Evidence