Methyl iodide → HCID 135955740, compound

Participants

Reaction Conditions

Reaction Steps

N-{3-[1-(3,3-Dimethyl-butyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,9,10,10a-decahydro-cycloocta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (prepared as described in Example 35b, 0.20 g, 0.36 mmol) was dissolved in N,N-dimethylformamide (12 mL). Potassium carbonate (0.10 g, 0.72 mmol) and iodomethane (0.025 mL, 0.40 mmol) were added sequentially. The reaction was stirred at 25° C. for 3 h. The reaction was quenched via the addition of 1.0 M aqueous hydrochloric acid solution (20 mL). The mixture was extracted with ethyl acetate (3×30 mL). The organic layers were combined and washed with saturated aqueous brine solution (20 mL) before they were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford a golden oil. Purification by flash column chromatography (Teledyne Isco RediSep Flash Column 12 g; 0-20% ethyl acetate in dichloromethane) afforded the desired product, N-{3-[1-(3,3-dimethyl-butyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,9,10,10a-decahydro-cycloocta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-N-methyl-methanesulfonamide (0.018 g, 0.23 mmol, 9%), as a white powder. 1H NMR (400 MHz, DMSO-d6) δ: 1.00-1.02 (9H, m), 1.35-1.80 (14H, m), 2.87-2.88 (3H, m), 3.00-3.35 (2H, m), 3.36-3.38 (3H, m), 3.86-4.15 (2H, m), 7.20-7.28 (1H, m), 7.64-7.79 (2H, m). LC-MS (ESI) calcd for C26H38N4O6S2 566.73, found 567.4 [M+H+].

Provenance & Evidence