Oxalyl chloride → HCID 58158588, compound

Participants

Reaction Steps

To a solution of 2-(4-fluorophenyl)-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (1130 mg, 4.5 mmol) in tetrahydrofuran (75 mL) were added N,N-dimethylformamide (6 drops) and oxalyl dichloride (780 μL, 9.1 mmol), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and the obtained residue was dissolved in N,N-dimethylacetamide (10 mL). The solution was added to a solution of N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (1230 mg, 3.8 mmol) in N,N-dimethylacetamide (30 mL), and the mixture was stirred at room temperature for 4 hr. Ethyl acetate/tetrahydrofuran and saturated aqueous sodium hydrogen carbonate solution were added to the mixture, and the aqueous layer was extracted 4 times with ethyl acetate/tetrahydrofuran. The combined organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate and collected by filtration to give the title compound (1640 mg, 67%) as a white solid.

Provenance & Evidence