2,4-Dichlorobenzylamine → HCID 25094896, compound

Participants

Reaction Steps

To a solution of 1-(6-fluoro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid TFA salt (200 mg, 0.836 mmol) and N-ethylmorpholine (0.635 ml, 5.02 mmol) in dichloromethane (10 ml) was added 1-hydroxybenzotriazole hydrate (128 mg, 0.836 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (160 mg, 0.836 mmol) and the mixture was stirred for 10 minutes. 1-(2,4-Dichlorophenyl)methanamine (147 mg, 0.836 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and 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 FFlashmaster automated silica gel chromatography eluting with 10-100% ethyl acetate in isohexane to give N-[(2,4-dichlorophenyl)methyl]-1-(6-fluoro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide (60 mg, 18% yield). LC/MS [M+H]+=397, retention time=2.63 minutes.

Provenance & Evidence