Ethylmorpholine → HCID 67460909, compound

Participants

Reaction Steps

1,3-Dimethyl-5-oxoproline (0.620 g, 3.6 mmol, prepared as described below), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.822 g, 4.3 mmol), 1-Hydroxybenzotriazole (0.581 g, 4.3 mmol), N-ethyl morpholine (1.4 ml, 10.8 mmol), and {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (0.828 g, 3.96 mmol) were combined in a mixture of dichloromethane (10 ml) and dimethylformamide (5 ml) and stirred under argon overnight. The mixture was then washed sequentially with water (50 ml), 0.5 N aqueous hydrogen chloride (50 ml), water (50 ml), saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml). The dichloromethane layer was passed through a hydrophobic frit and evaporated in vacuo to give the crude product. This was further purified by mass-directed automated HPLC (10×0.100 g injections) to give pure N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1,3-dimethyl-5-oxoprolinamide (0.613 g).

Provenance & Evidence