Propionic Acid → N-[5-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-propionamide

Participants

Reaction Steps

To a solution of 6-(5-aminomethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one (example 36, 0.05 g, 0.187 mmol) in dry DMF (1 mL) were added EDCI (0.039 g, 0.206 mmol), Hünig's base (0.060 g, 0.468 mmol) and propionic acid (0.021 g, 0.282 mmol) and the reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with EtOAc, poured into sat. NH4Cl solution (5 mL) and extracted with EtOAc (2×10 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 10% MeOH(1% NH4OH)-DCM gradient to give the title compound (0.029 g, 48%) as a white solid. MS: 324.4 (M+H+).

Provenance & Evidence