2-(4-((1-(2,5-Difluorophenyl)propan-2-yl)amino)-2-oxo-1,2-dihydropyridin-3-yl)-6-(1-methylpiperidin-4-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione → 2-(4-(1-(2,5-Difluorophenyl)propan-2-ylamino)-2-oxo-1,2-dihydropyridin-3-yl)-6-(1-methylpiperidin-4-yl)-6,7-dihydroimidazo[4,5-f]isoindol-5(1H)-one

Participants

Reaction Steps

To a solution of 2-(4-(1-(2,5-difluorophenyl)propan-2-ylamino)-2-oxo-1,2-dihydropyridin-3-yl)-6-(1-methylpiperidin-4-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (0.30 g, 0.53 mmol) in 50 mL of acetic acid was added zinc powder (0.64 g, 9.78 mmol). The mixture was heated to reflux for 16 h and filtered through Celite. Acetic acid was removed under vacuum and the residue was taken up with 10 mL of MeOH. Reverse phase chromatography purification yielded the title compound as a white solid (39 mg, 13.8%). 1H NMR δ (500 MHz, DMSO-d6) 13.05 (d, J=3.5 Hz, 1H), 11.23 (t, J=6.5 Hz, 1H), 11.10 (d, J=7.5 Hz, 1H), 7.96 (s, 0.5H, conformational isomer), 7.85 (s, 0.5H), 7.81 (s, 0.5H), 7.68 (s, 0.5H), 7.44-7.30 (m, 2H), 7.22-7.14 (m, 1H), 7.11-7.02 (m, 1H), 6.17 (d, J=8.0 Hz, 1H), 4.48 (s, 2H), 4.18-4.08 (m, 1H), 4.08-3.98 (m, 1H), 3.08-3.02 (m, 1H), 3.02-2.94 (m, 1H), 2.91 (d, J=10.5 Hz, 2H), 2.23 (s, 3H), 2.11-2.02 (m, 2H), 1.90-1.78 (m, 2H), 1.74-1.66 (m, 2H), 1.34-1.29 (m, 3H). ESI MS: m/z 533.02 (M+1).

Provenance & Evidence