(S)-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 → HCID 178461706, compound

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Reaction Steps

To a solution of (S)-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 (Compound 27) (0.30 g, 0.51 mmol) in 50 mL of acetic acid was added zinc powder (0.64 g, 7.65 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 (40 mg, 13.7%). 1H NMR δ (500 MHz, DMSO-d6) 13.03 (d, J=3.0 Hz, 1H), 11.25 (br s, 1H), 11.11 (dd, J=5, 13 Hz, 1H), 7.96 (s, 0.5H, conformational isomer), 7.81 (s, 0.5H), 7.77 (s, 0.5H), 7.80-7.65 (m, 1H), 7.61 (s, 0.5H), 7.41-7.31 (m, 1H), 6.16 (d, J=12.0 Hz, 1H), 4.48 (s, 2H), 4.29-4.14 (m, 1H), 4.12-3.96 (m, 1H), 3.20-3.02 (m, 2H), 2.90 (d, J=18 Hz, 2H), 2.23 (s, 3H), 2.07 (t, J=18 Hz, 2H), 1.94-1.75 (m, 2H), 1.78-1.64 (m, 2H), 1.42-1.29 (m, 3H). ESI MS: m/z 569.2 (M+1).

Provenance & Evidence