Dichloromethane → N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-(1-methyl-1H-imidazol-4-yl)-2-oxo-4-imidazolidinecarboxamide

Participants

Reaction Steps

A solution of 3-methyl-1-(1-methyl-1H-imidazol-4-yl)-2-oxo-4-imidazolidinecarboxylic acid trifluoroacetate salt (145 mg, 0.647 mmol) in dichloromethane (4 ml) was treated with 1-hydroxyorthobenzatriazole hydrate (119 mg, 0.776 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (149 mg, 0.776 mmol) & N-ethylmorpholine (0.491 ml, 3.88 mmol) and the mixture stirred at room temp for 10 minutes. 1-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}amine (136 mg, 0.647 mmol) was then added and the reaction stirred at room temp over the weekend. The reaction was diluted with dichloromethane and washed with 3N citric acid, saturated sodium hydrogen carbonate solution, water and brine, separated through a hydrophobic frit and the organic layer reduced under vacuum. The residue was purified by mass-directed automated HPLC and freeze dried to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-(1-methyl-1H-imidazol-4-yl)-2-oxo-4-imidazolidinecarboxamide (30 mg, 10.6% yield). LC/MS [M+H]+=416, retention time=1.92 minutes.

Provenance & Evidence