Diisopropylethylamine → 2-(2-methyl-3-((1-methylcyclobutyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-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; 41.6 mg, 0.094 mmol), 1-methylcyclobutanamine hydrochloride (ChemBridge, San Diego, Calif.; 34.3 mg, 0.282 mmol), and DIPEA (0.098 mL, 0.564 mmol) in DMSO (0.8 mL), heating at 90° C. for 19 h. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(2-methyl-3-((1-methylcyclobutyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (26.4 mg, 0.073 mmol, 78% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.29 (1H, br. s.), 7.89 (1H, d, J=6.8 Hz), 7.56 (1H, d, J=7.2 Hz), 7.32 (1H, t, J=7.8 Hz), 7.04 (1H, d, J=1.8 Hz), 7.01 (1H, s), 6.98 (1H, br. s.), 3.45 (2H, td, J=6.8, 2.2 Hz), 2.92 (2H, t, J=6.7 Hz), 2.56 (3H, s), 2.42-2.49 (2H, m), 2.21-2.30 (2H, m), 1.86-2.00 (2H, m), 1.69 (3H, s). m/z (ESI, +ve) 362.3 (M+H)+.

Provenance & Evidence