Methanol → 2-(4-((cyclopropylamino)methyl)pyridin-3-yl)-7-(trifluoromethyl)-3,4-dihydroisoquinolin-1(2H)-one

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Reaction Steps

Cyclopropanamine (25.8 μL, 0.3737 mmol) was added to a stirred solution of 3-(1-oxo-7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)isonicotinaldehyde (I-53c: 100 mg, 0.3114 mmol) in acetic acid (5 mL) and resulting reaction mixture was stirred for 4 hours at room temperature. The reaction mass was cooled to 0° C. and added NaBH(OCH3)3 (99 mg, 0.4674 mmol). The resulting reaction mass was stirred for 12 hours at room temperature. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mass was concentrated under reduced pressure, the crude residue obtained was diluted with ice, basified using saturated NaHCO3 solution to pH 7 and extracted using CHCl3. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 25 mg of the product (22% yield).

Provenance & Evidence