2-Methylallylamine → HCID 89784464, compound

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; 45.5 mg, 0.107 mmol) and 2-methylallylamine (Matrix Scientific, Columbia, S.C.; 0.039 mL, 0.430 mmol) in DMSO (0.8 mL), heating at 80° C. for 30 min. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(2-methyl-3-((2-methylallyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (22.0 mg, 0.063 mmol, 59% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.83 (1H, br. s.), 7.87 (1H, dd, J=7.6, 1.2 Hz), 7.59 (1H, t, J=5.6 Hz), 7.56 (1H, m, J=8.0, 1.2 Hz), 7.31 (1H, t, J=7.8 Hz), 7.10 (1H, d, J=2.2 Hz), 6.93 (1H, s), 4.86 (1H, s), 4.83 (1H, s), 4.05 (2H, d, J=5.7 Hz), 3.42 (2H, td, J=6.8, 2.3 Hz), 2.86 (2H, t, J=6.8 Hz), 2.57 (3H, s), 1.85 (3H, s). m/z (ESI, +ve) 348.2 (M+H)+.

Provenance & Evidence