Diisopropylethylamine → 1H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-one

Participants

Reaction Conditions

Reaction Steps

Prepared similar to that described in Example 131 using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 46.7 mg, 0.106 mmol), 3,3-difluorocyclobutanamine hydrochloride (PharmaStone, Lexington, Mass.; 45.5 mg, 0.317 mmol), and DIPEA (0.110 mL, 0.634 mmol) in DMSO (0.8 mL), heating at 80° C. for 1.5 h. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2434(3,3-difluorocyclobutyl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (26.5 mg, 0.069 mmol, 66% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.97 (1H, br. s.), 7.88 (1H, dd, J=7.6, 1.2 Hz), 7.60 (1H, dd, J=8.0, 1.0 Hz), 7.51 (1H, d, J=5.5 Hz), 7.37 (1H, t, J=7.8 Hz), 7.06 (1H, d, J=2.2 Hz), 6.94 (1H, br. s.), 4.39-4.51 (1H, m), 3.45 (2H, td, J=6.7, 2.5 Hz), 3.04-3.15 (2H, m), 2.88 (2H, t, J=6.7 Hz), 2.86-2.92 (2H, m), 2.57 (3H, s). 19F NMR (377 MHz, DMSO-d6) δ ppm −82.16 to −81.43 (1F, m), −95.87 to −95.05 (1F, m). m/z (ESI, +ve) 384.2 (M+H)+.

Provenance & Evidence