2,4-Dichlorobenzylamine → N-[(2,4-dichlorophenyl)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 (0.105 g, 0.47 mmol) (prepared as described in step (ii) of Example 57) and N-ethyl morpholine (0.361 ml, 2.82 mmol) in dichloromethane (5 ml) was treated with 1-hydroxybenzotriazole hydrate (0.086 g, 0.564 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.090 g, 0.470 mmol) and stirred at room temperature for 10 minutes. 1-(2,4-Dichlorophenyl)methanamine (0.063 ml, 0.470 mmol) was added and the reaction mixture was stirred over the weekend. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine and separated using a hydrophobic frit. The filtrate was concentrated under vacuum and purified by mass-directed automated HPLC to give N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-(1-methyl-1H-imidazol-4-yl)-2-oxo-4-imidazolidinecarboxamide (26 mg, 13.75% yield). LC/MS [M+H]+=382, retention time=1.83 minutes.

Provenance & Evidence