Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-3-fluorophenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Participants

Reaction Steps

N-[5-(4-Amino-2-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (240 mg, 0.70 mmol), 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (190 mg, 0.77 mmol) and HATU (340 mg, 0.91 mmol) were suspended in N,N′-dimethylformamide (3.0 mL), and N,N-diisopropylethylamine (0.24 mL, 1.4 mmol) was added. After stirring at room temperature for 8 hr, the mixture was diluted with ethyl acetate (5.0 mL) and tetrahydrofuran (5.0 mL). The mixture was washed twice with saturated aqueous sodium hydrogen carbonate solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and ethyl acetate was added to the residue. The resulting precipitate was collected by filtration to give the title compound (350 mg, 0.61 mmol, 88%) as a pale-yellow solid.

Provenance & Evidence