Diisopropylethylamine → 2-(2-methyl-3-((4-methyltetrahydro-2H-pyran-4-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Participants

Reaction Conditions

Reaction Steps

Prepared similarly 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; 48 mg, 0.162 mmol), 4-methyltetrahydro-2H-pyran-4-amine hydrochloride (49.1 mg, 0.324 mmol, Biofine International, Blaine, Wash.), and DIPEA (141 μl, 0.810 mmol), heating at 100° C. for 20 h. Purification by silica gel (100% DCM to 5% MeOH/DCM) provided 2-(2-methyl-3-((4-methyltetrahydro-2H-pyran-4-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (6% yield). 1H NMR (400 MHz, MeOD) δ ppm 1.73 (s, 3H) 1.85-1.95 (m, 2H) 2.53 (d, J=13.50 Hz, 2H) 2.67 (s, 3H) 3.01 (t, J=7.14 Hz, 2H) 3.64 (t, J=7.14 Hz, 2H) 3.76-3.82 (m, 4H) 7.00 (s, 1H) 7.40 (t, J=7.82 Hz, 1H) 7.65 (dd, J=8.12, 1.27 Hz, 1H) 7.88 (dd, J=7.53, 1.27 Hz, 1H). MS (ESI, pos. ion) m/z: 392.1 (M+1).

Provenance & Evidence