Ethylmorpholine → N-[(2-Chloro-3,4-difluorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide

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Reaction Steps

A mixture of 3-methyl-2-oxo-4-imidazolidinecarboxylic acid (115 mg, 0.8 mmol), 1-hydroxybenzotriazole hydrate (147 mg, 0.96 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (184 mg, 0.96 mmol) and N-ethyl morpholine (0.613 ml, 4.8 mmol) in dichloromethane (18 ml) was stirred at room temperature for 10 minutes. A solution of [(2-chloro-3,4-difluorophenyl)methyl]amine (142 mg, 0.8 mmol) in dichloromethane (2 ml) was added and the reaction stirred at room temperature for 18 hours. The mixture was diluted with dichloromethane (60 ml) and the mixture was washed with 3N citric acid solution (30 ml). The organic phase was separated, washed with brine, dried and evaporated. The residue was purified by mass-directed automated HPLC to give N-[(2-Chloro-3,4-difluorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (95 mg, 39%). LC/MS [M+H]+=304, retention time=1.99 minutes.

Provenance & Evidence