2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → N-{[2-chloro-4-fluoro-3-(trifluoromethyl)phenyl]methyl}-1-methyl-5-oxoprolinamide

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Reaction Steps

1-methyl-5-oxoproline (0.057 g, 0.4 mmol, prepared in a manner analogous to that described above for example 51) dissolved in dichloromethane (4 ml) and treated with 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.104 g, 0.42 mmol). {[2-Chloro-4-fluoro-3-(trifluoromethyl) phenyl]methyl}amine hydrochloride (0.105 g, 0.4 mmol, prepared as described below) was then added and the mixture was stirred at room temperature for 4 hrs. The mixture was treated with saturated aqueous sodium hydrogen carbonate (10 ml) and stirred for 5 minutes. The organic phase was separated using a hydrophobic frit and then washed with 2N aqueous hydrogen chloride (2×10 ml). Evaporation of the organic phase then gave pure N-{[2-chloro-4-fluoro-3-(trifluoromethyl)phenyl]methyl}-1-methyl-5-oxoprolinamide (0.106 g).

Provenance & Evidence