2,4-Dichlorobenzylamine → n-[(2,4-Dichlorophenyl)methyl]-3-methyl-1-[6-(methyloxy)-3-pyridinyl]-2-oxo-4-imidazolidinecarboxamide

Participants

Reaction Steps

To a solution of 3-methyl-1-[6-(methyloxy)-3-pyridinyl]-2-oxo-4-imidazolidinecarboxylic acid TFA salt (145 mg, 0.404 mmol) and N-ethylmorpholine (0.307 ml, 2.424 mmol) in dichloromethane (5 ml) was added 1-hydroxybenzotriazole hydrate (61.9 mg, 0.404 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (77 mg, 0.404 mmol) and the reaction mixture was stirred for 10 minutes at room temperature. 1-(2,4-Dichlorophenyl)methanamine (71.1 mg, 0.404 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and the solution was washed with saturated sodium hydrogen carbonate solution, water and brine, separated through a hydrophobic frit and the organic layer was reduced under vacuum. The residue was purified by SP4 automated silica gel chromatography eluting with 10-100% ethyl acetate in isohexane to give N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-[6-(methyloxy)-3-pyridinyl]-2-oxo-4-imidazolidinecarboxamide (101 mg, 59.9% yield). LC/MS [M+H]+=409, retention time=2.34 minutes.

Provenance & Evidence