Triethylamine → HCID 10136942, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-aminopyridine (25 mg, 0.26 mmol) in acetonitrile (500 μL) was treated with 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionic acid (75 mg, 0.22 mmol), triphenylphosphine (63 mg, 0.24 mmol), triethylamine (91 μL, 0.66 mmol), and carbon tetrachloride (300 μL). The resulting reaction mixture was stirred at 25° C. for 15 h. The cloudy reaction mixture was diluted with water and then extracted with methylene chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) afforded impure 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-N-pyridin-2-yl-propionamide. Repurification by flash chromatography (Merck Silica gel 60, 230-400 mesh, 100% methylene chloride) afforded pure 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-N-pyridin-2-yl-propionamide. (40 mg, 43%) as a white foam: mp 73-77° C.; EI-HRMS m/e calcd for C29H28N2O (M+) 420.2202, found 420.2003.

Provenance & Evidence