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 DCM (1 mL) were added EDCI (0.039 g, 0.206 mmol), hydroxybenzotriazole (0.032 g, 0.206 mmol), Hünig's base (0.060 g, 0.468 mmol) and 3-methoxy-isoxazole-5-carboxylic acid (0.040 g, 0.281 mmol) and the resulting solution was stirred at room temperature over night. The reaction mixture was diluted with EtOAc, poured into sat. NaHCO3 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 (0.03 g, 41%) as a white solid. MS: 393.1 (M+H+).
