2-Aminocyclohexanol → 1H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-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) and 2-aminocyclohexanol (37.0 mg, 0.324 mmol, TCI America, Portland, Oreg.; mixture of racemic cis- and trans-isomers) and heating at 100° C. for 2 h. Purification by silica gel (100% DCM to 8% MeOH/DCM) provided 2434(2-hydroxycyclohexyl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (24% yield; mixture of racemic cis- and trans-isomers). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37-1.50 (m, 2H) 1.54-1.86 (m, 6H) 2.56 (s, 3H) 2.88 (t, J=6.85 Hz, 2H) 3.44 (td, J=6.75, 2.15 Hz, 2H) 4.08 (br. s., 2H) 4.84 (br. s., 1H) 6.23 (d, J=7.04 Hz, 1H) 6.89 (br. s., 1H) 7.14 (d, J=2.15 Hz, 1H) 7.32 (t, J=7.82 Hz, 1H) 7.56 (d, J=6.85 Hz, 1H) 7.86 (d, J=6.26 Hz, 1H) 11.86 (br. s., 1H). MS (ESI, pos. ion) m/z: 392.3 (M+1).

Provenance & Evidence