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

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Reaction Steps

To a solution of 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (56.7 mg, 0.229 mmol) and N-[6-(4-amino-2-fluorophenoxy)-3-methylimidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (60 mg, 0.176 mmol) in N,N-dimethylformamide (1 mL) were added N,N-diisopropylethylamine (61 μL, 0.352 mmol) and HATU (87 mg, 0.229 mmol), and the mixture was stirred at room temperature for 17 hr. 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 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 yellow oil. The obtained oil was dissolved in ethyl acetate (1 mL) and left standing at room temperature for 17 hr. The precipitated solid was collected by filtration, washed with diethyl ether and collected by filtration to give the title compound (76 mg, 75%) as a white solid.

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