Triethylamine → HCID 10184740, compound

Participants

Reaction Steps

320 mg (1.7 mmol) of 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride are added portionwise, at 0° C., to a solution of 270 mg (1.5 mmol) of 4-acetamidobenzoic acid, 230 μl (1.6 mmol) of triethylamine, 230 mg (1.7 mmol) of 1-hydroxybenzo-triazole and 500 mg (1.5 mmol) of 5-(3′-methylamino-methylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione in 5 ml of dichloromethane. The reaction medium is stirred at from 0° C. to room temperature for 18 hours, washed with saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 99/1 dichloromethane/methanol mixture. After evaporation of the solvents, 600 mg (80%) of 4-acetylamino-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylbenzamide are obtained in the form of a white solid with a melting point of 207° C.

Provenance & Evidence