Reaction Steps
A mixture of 4-methyl-6-(1-methylpiperidin-4-yl)-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 (0.93 g, 1.65 mmol), zinc dust (1.02 g, 15.6 mmol), and 30 mL of acetic acid was heated at reflux for 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 0.33 g (36.3%) of the designed compound as yellowish solid. NMR (500 MHz, DMSO-d6) δ 12.95 (s, 1H, NH), 11.32 (d, J=8.5 Hz, 1H, NH), 11.25 (d, J=4.1 Hz, 1H, NH), 7.80 (s, 1H, ArH), 7.77-7.75 (m, 1H, ArH), 7.63 (t, J=7.0 Hz, 1H, ArH), 6.19 (d, J=7.5 Hz, 1H, ArH), 4.41 (d, J=3.5 Hz, 2H, CH2), 4.29-4.21 (m, 1H, CH), 4.06-4.01 (m, 1H, CH), 3.07-3.06 (m, 2H, CH2), 2.92-2.90 (m, 2H, CH2), 2.43 (s, 3H, CH3), 2.24 (s, 3H, CH3), 2.09 (m, 2H, CH2), 1.91-1.83 (m, 2H, CH2), 1.72-1.69 (m, 2H, CH2), 1.36 (d, J=6.5 Hz, 3H, CH3); Mass (ESI, positive) m/z 583.2 [M+H]+.
