Diisopropylethylamine → rac-2-(2-methyl-3-((2-oxopiperidin-3-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Participants

Reaction Conditions

Reaction Steps

Prepared similar 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; 42 mg, 0.142 mmol), rac-aminopiperidin-2-one hydrochloride (42.7 mg, 0.283 mmol, Matrix Scientific, Inc., Columbia, S.C.), and DIPEA (123 μl, 0.709 mmol), heating at 100° C. for 1.5 h. Purification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA) and silica gel (100% DCM to 10% MeOH/DCM) provided rac-2-(2-methyl-3-((2-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 1.82-2.01 (m, 3H) 2.27-2.37 (m, 1H) 2.57 (s, 3H) 2.83-2.91 (m, 2H) 3.21-3.29 (m, 2H) 3.45 (td, J=6.94, 2.35 Hz, 2H) 4.63-4.72 (m, 1H) 6.94 (s, 1H) 7.05-7.13 (m, 2H) 7.36 (t, J=7.82 Hz, 1H) 7.60 (dd, J=8.02, 1.17 Hz, 1H) 7.82-7.89 (m, 2H) 11.85 (br. s., 1H). MS (ESI, pos. ion) m/z: 391.1 (M+1).

Provenance & Evidence