Dimethylformamide → HCID 19593051, compound

Participants

Reaction Steps

To a mixture of dimethylformamide (17.4 mg) and dichloromethane was added oxalyl chloride (27.7 mg), and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added 3-bromo-4-carboxymethyl-8-(2,6-dichlorobenzoylamino)quinoline (90 mg) at 0° C., and the mixture was stirred for 1 hour at the same temperature. To the mixture was added 2-aminomethylpyridine (107 mg) at 0° C., and the mixture was stirred for 30 minutes at ambient temperature. The mixture was partitioned between dichloromethane and saturated ammonium chloride solution. The organic layer was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography and recrystallized from ethanol to give 3-bromo-8-(2,6-dichlorobenzoylamino)-4-[(pyridin-2-ylmethyl)carbamoylmethyl]quinoline (58.0 mg).

Provenance & Evidence