Diisopropylethylamine → 2-(3-(3,3-dimethylmorpholino)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 210 using 2-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 210i; 65 mg, 0.230 mmol), 3,3-dimethylmorpholine hydrochloride (69.8 mg, 0.461 mmol, Tyger Scientific, Ewing, N.J.), and DIPEA (201 μl, 1.151 mmol), heating at 100° C. for 3 h. Purification by silica gel (100% DCM to 4% MeOH/DCM) provided 2-(3-(3,3-dimethylmorpholino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (12% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (s, 6H) 2.92 (t, J=6.85 Hz, 2H) 3.46-3.50 (m, 2H) 3.51 (s, 2H) 3.74-3.79 (m, 2H) 3.90-3.94 (m, 2H) 7.00 (br. s., 1H) 7.12 (d, J=2.15 Hz, 1H) 7.59 (t, J=7.82 Hz, 1H) 7.81 (dd, J=8.12, 1.27 Hz, 1H) 7.96 (dd, J=7.53, 1.27 Hz, 1H) 8.91 (s, 1H) 11.69 (br. s., 1H). MS (ESI, pos. ion) m/z: 378.0 (M+1).

Provenance & Evidence