Diisopropylethylamine → HCID 89783585, 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; 48 mg, 0.162 mmol), rac-5-aminopiperidin-2-one hydrochloride (48.8 mg, 0.324 mmol, Advanced ChemBlocks, Inc., Burlingame, Calif.), and DIPEA (141 μl, 0.810 mmol), heating at 100° C. for 1.5 h. Purification by silica gel (100% DCM to 20% MeOH/DCM) provided rac-2-(2-methyl-3-((6-oxopiperidin-3-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (33% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.93-2.07 (m, 1H) 2.14-2.23 (m, 1H) 2.31-2.41 (m, 1H) 2.58 (s, 3H) 2.83-2.90 (m, 2H) 3.23-3.29 (m, 1H) 3.44 (td, J=6.85, 2.15 Hz, 2H) 3.51-3.59 (m, 1H) 4.39-4.51 (m, 1H) 6.94 (br. s., 1H) 7.00 (d, J=6.65 Hz, 1H) 7.13 (s, 1H) 7.37 (t, J=7.82 Hz, 1H) 7.50 (d, J=2.15 Hz, 1H) 7.61 (d, J=7.04 Hz, 1H) 7.89 (d, J=7.63 Hz, 1H) 11.90 (br. s., 1H). MS (ESI, pos. ion) m/z: 391.3 (M+1).

Provenance & Evidence