Diisopropylethylamine → HCID 22348261, compound

Participants

Reaction Steps

To a solution of 6-methoxy-1-methyl-4-(piperidin-4-ylamino)-1H-quinolin-2-one (300 mg, 0.8 mmol) and diisopropylethlyamine (705 uL, 4 mmol) in DMF (5 mL) was added a solution of 3,4 methylenedioxybenzyl chloride in methylene chloride (231 uL, 0.9 mmol, 50% by weight in CH2Cl2). After stirring at room temperature for 2 hours, the reaction mixture was diluted up with methylene chloride, washed with brine and dried with MgSO4. The residue was purified by flash chromatography through a silica gel column with dichloromethane and methanol (95:5 v/v) to provide the title compound (66.4 mg, 20%): 1H NMR (300 MHz, CDCl3) δ 1.58-1.72 (2H, m), 2.10-2.23 (4H, m), 2.88-2.98 (2H, m), 3.40-3.50 (1H, m), 3.48 (3H, s), 3.64 (3H, s), 4.58 (1H, bd, J=7.5), 5.75 (1H, s), 5.95 (2H, s), 6.77 (2H, s), 6.89 (1H, s), 7.25 (1H, d; J=1.89 Hz), 7.26 (1H, s), 7.40 (1H, dd, j=1.79, 8.75 Hz).

Provenance & Evidence