Triethylamine → N-[6-(2-Chlorophenyl)-1-(cyclopropylmethyl)-2-oxo-1,2-dihydropyridin-3-yl]-4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)piperidine-1-carboxamide

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Reaction Steps

Triethylamine (9 μL, 0.062 mmol) was added to a solution of amino-6-(2-chlorophenyl)-1-(cyclopropylmethyl)pyridin-2(1H)one (17 mg, 0.062 mmol) and 4-nitrophenyl chloroformate (13 mg, 0.062 mmol) in tetrahydrofuran (2 mL) at 0° C. After 0.5 h, 4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)piperidinium chloride (20 mg, 0.071 mmol) and triethylamine (0.030 mL, 0.215 mmol) were added and the mixture allowed to warm to ambient temperature. After 2 h, the mixture was concentrated in vacuo. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) followed by reverse phase HPLC(C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (5 mg). MS 544.2 (M+1).

Provenance & Evidence