Acetyl chloride → HCID 57786724, compound

Participants

Reaction Conditions

Reaction Steps

To N-[3-(8-Amino-imidazo[1,2-a]pyridin-6-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide (185 mg, 0.414 mmol) in dichloromethane (10 mL) was added diisopropylethylamine (0.24 mL, 3 eq). The resulting mixture was cooled to 0° C. and with stirring was added acetyl chloride (31 μL, 0.95 eq) and the resulting mixture was stirred from 0° C. to room temperature overnight. The next day the solvent was removed under reduced pressure at 55° C. and ethyl acetate (35 mL) and water (25 mL) were added to the residue. The organic layer was concentrated. Then added THF (5 mL) and 1N NaOH (5 mL) and stirred vigorously at room temperature overnight to hydrolize significant bis-amide. The next day added ethyl acetate (150 mL) and water (50 mL) and added 1N HCl to pH=2 and stirred vigorously for 10 minutes. The layers were separated, and the organic layer was washed with brine (1×50 mL), and then dried over magnesium sulfated, filtered and concentrated. The crude product was purified by Thin Layer Chromatography, eluting with 5% methanol in dichloromethane to give the title compound as an off-white powder (31 mg), ((M+H)+=441).

Provenance & Evidence