Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-3-fluorophenyl]-N'-phenylcyclopropane-1,1-dicarboxamide

Participants

Reaction Steps

To a solution of N-[5-(4-amino-2-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (150 mg, 0.436 mmol) in N,N-dimethylacetamide (3.0 mL) were added 1-(phenylcarbamoyl)cyclopropanecarboxylic acid (134 mg, 0.653 mmol), HATU (248 mg, 0.653 mmol) and N,N-diisopropylethylamine (114 μL, 0.653 mmol), and the mixture was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The 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 (ethyl acetate alone). The obtained powder was washed with hexane/ethyl acetate and collected by filtration to give the title compound (175 mg, 76%).

Provenance & Evidence