Diisopropylethylamine → HCID 178432137, compound

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), cis-4-aminocyclohexanol (42.0 mg, 0.277 mmol, J&W Pharmlab, Levittown, Pa.), and DIPEA (121 μl, 0.692 mmol), heating at 100° C. for 1 h. Purification by silica gel (100% DCM to 10% MeOH/DCM) provided 2-(3-((cis-4-hydroxycyclohexyl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (26% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.61-1.71 (m, 2H) 1.72-1.83 (m, 4H) 1.83-1.96 (m, 2H) 2.56 (s, 3H) 2.89 (t, J=6.85 Hz, 2H) 3.41-3.48 (m, 2H) 3.88 (br. s., 1H) 3.97-4.07 (m, 1H) 4.42 (br. s., 1H) 6.77 (d, J=7.04 Hz, 1H) 6.91 (br. s., 1H) 7.18 (d, J=1.76 Hz, 1H) 7.31 (t, J=7.82 Hz, 1H) 7.55 (d, J=7.82 Hz, 1H) 7.87 (d, J=7.63 Hz, 1H) 11.94 (br. s., 1H). MS (ESI, pos. ion) m/z: 392.1 (M+1).

Provenance & Evidence