2,4-Dichlorobenzylamine → HCID 25094898, compound

Participants

Reaction Steps

To a solution of 1-(2-fluoro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid TFA salt (182 mg, 0.761 mmol) and N-ethylmorpholine (0.578 ml, 4.57 mmol) in dichloromethane (5 ml) was added 1-hydroxybenzotriazole hydrate (117 mg, 0.761 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (146 mg, 0.761 mmol) and the reaction mixture was stirred for 10 minutes at room temperature. 1-(2,4-Dichlorophenyl)methanamine (134 mg, 0.761 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]-1-(2-fluoro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide (125 mg, 40.5% yield)

Provenance & Evidence