Reaction Steps
A mixture of 6-(2-(dimethylamino)ethyl)-4-methyl-2-(2-oxo-4-(1-(2,3,5,6-tetrafluorophenyl)propan-2-ylamino)-1,2-dihydropyridin-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (0.25 g, 0.44 mmol), zinc dust (0.29 g, 4.38 mmol), and 7.5 mL of acetic acid was heated at reflux for 13-14 h under an argon atmosphere. Product was separated by a silica gel column using methylene chloride and methanol (85:15 v/v) as eluent to afford 30 mg of the designed compound as yellowish solid. NMR (500 MHz, DMSO-d6) δ 12.93 (s, 1H, NH), 11.28 (d, J=8.5 Hz, 1H, NH), 11.27 (s, 1H, NH), 7.78-7.74 (m, 1H, ArH), 7.59 (s, 1H, ArH), 7.37 (d, 0.1=7.5 Hz, 1H, ArH), 6.20 (d, J=7.5 Hz, 1H, ArH), 4.46 (s, 2H, CH2), 4.30-4.27 (m, 1H, CH), 3.60-3.57 (m, 2H, CH2), 3.08-3.06 (m, 2H, CH2), 2.48 (m, 2H, CH2), 2.19 (s, 6H, 2×CH3), 1.83 (s, 3H, CH3), 1.36 (d, J=6.5 Hz, 3H, CH3); Mass (ESI, positive) m/z 557.2 [M+H]+.
