Acetic Acid → HCID 70874148, compound

Participants

Reaction Steps

The 5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-3-(methyl(piperidine-4-yl)amino)benzamide (0.2 g, 0.447 mmol) dissolved in DMSO (2 mL) and acetic acid (0.054 g, 0.896 mmol) were added to it. The reaction mixture was stirred at room temperature for 15 min before PYBOP (0.342 g, 0.672 mmol) was added to it and stirring was continued for overnight. After completion, reaction mass was poured into ice, and extracted using 10% MeOH/DCM. Combined organic layers were dried, concentrated to provide crude material, which then purified with column chromatography using silica (100-200 mesh size) to afford the desired compound (0.15 g, 17%). LCMS: 503.20 (M+1)+; HPLC: 96.06% (@ 254 nm) (Rt; 5.143; Method: Column: YMC ODS-A 150 mm×4.6 mm×5μ; Mobile Phase: A; 0.05% TFA in water/B; 0.05% TFA in acetonitrile; Inj. Vol: 10 μL, Col. Temp.: 30° C.; Flow rate: 1.4 mL/min.; Gradient: 5% B to 95% B in 8 min, Hold for 1.5 min, 9.51-12 min 5% B); 1H NMR (DMSO-d6, 400 MHz) δ 11.48 (s, 1H), 8.21 (t, 1H, J=4.8 Hz), 7.23 (d, 1H, J=1.6 Hz), 7.04 (d, 1H, J=1.6 Hz), 5.85 (s, 1H), 4.32 (d, 1H, J=12.4 Hz), 4.23 (d, 2H, J=4.8 Hz), 3.77 (d, 1H, J=13.2 Hz), 2.98 (t, 2H, J=11.2 Hz), 2.54 (s, 3H), 2.18 (s, 3H), 2.13 (s, 3H), 2.10 (s, 3H), 1.97 (s, 3H), 1.53-1.60 (m, 4H), 1.38-1.41 (m, 1H).

Provenance & Evidence