2,4-Dichlorobenzylamine → HCID 25095177, compound

Participants

Reaction Steps

To a solution of 1-(2-chloro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid (179 mg, 0.484 mmol) and N-ethylmorpholine (0.368 ml, 2.91 mmol) in dichloromethane (5 ml) was added 1-hydroxybenzotriazole hydrate (111 mg, 0.726 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (139 mg, 0.726 mmol) and the mixture was stirred for 10 minutes at room temperature. 1-(2,4-Dichlorophenyl)methanamine (128 mg, 0.726 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine and separated by hydrophobic frit and the solution was reduced under vacuum. The residue was purified by SP4 automated silica gel chromatography eluting with 10-100% ethyl acetate in isohexane to give 1-(2-chloro-3-pyridinyl)-N-[(2,4-dichlorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (60 mg, 27.6% yield). LC/MS [M+H]+=413, retention time=2.21 minutes

Provenance & Evidence