Diisopropylethylamine → 2-(2-methyl-3-(oxetan-3-ylamino)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; 41 mg, 0.138 mmol), oxetan-3-amine hydrochloride (30.3 mg, 0.277 mmol, Frontier Scientific), and DIPEA (121 μl, 0.692 mmol), heating at 100° C. for 30 min. Purification by silica gel (100% DCM to 8% MeOH/DCM) provided 2-(2-methyl-3-(oxetan-3-ylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (66% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.60 (s, 3H) 2.92 (t, J=6.85 Hz, 2H) 3.45 (td, J=6.85, 2.35 Hz, 2H) 4.74 (t, J=6.16 Hz, 2H) 4.98 (t, J=6.16 Hz, 2H) 5.04-5.15 (m, 1H) 6.98 (br. s., 1H) 7.10 (d, J=2.15 Hz, 1H) 7.37 (t, J=7.73 Hz, 1H) 7.60 (dd, J=8.02, 1.17 Hz, 1H) 7.70 (d, J=4.69 Hz, 1H) 7.85 (dd, J=7.63, 1.17 Hz, 1H) 11.80 (br. s., 1H). MS (ESI, pos. ion) m/z: 350.1 (M+1).

Provenance & Evidence