Diisopropylethylamine → N-[3-chloro-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 Conditions

Reaction Steps

To a solution of N-[6-(4-amino-2-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (100 mg, 0.292 mmol) and 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (94 mg, 0.38 mmol) in N,N-dimethylformamide (1 mL) were added N,N-diisopropylethylamine (100 μL, 0.583 mmol) and HATU (144 mg, 0.380 mmol), and the mixture was stirred at 60° C. for 4 hr. Ethyl acetate, tetrahydrofuran and saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The 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 purified by silica gel column chromatography (ethyl acetate alone) to give a white solid. The obtained solid was washed with ethyl acetate and collected by filtration to give the title compound (120.2 mg, 72%) as a white solid.

Provenance & Evidence