Water → Propane-2-sulfonic acid [5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

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Reaction Conditions

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 DCM (1 mL) cooled to 0° C. were added triethylamine (0.038 g, 0.374 mmol) and isopropylsulfonylchloride (0.029 g, 0.206 mmol). The resulting suspension was stirred at 0° C. for 4 h and then allowed to warm up to room temperature and stirring was continued for 2 h. The reaction mixture was diluted with DCM, poured into H2O (5 mL) and extracted with DCM (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 (0.023 g, 33%) as a white foam. MS: 374.1 (M+H+).

Provenance & Evidence