Hydrochloric Acid → HCID 136397072, compound

Participants

Reaction Steps

To a solution of Example 83B (138 mg, 0.26 mmol) in N,N-dimethylformamide (1 mL) was added potassium carbonate (70 mg, 0.51 mmol) and 3,5-dimethoxybenzenesulfonyl chloride (61 mg, 0.26 mmol) and the solution was stirred at room temperature for 16 hours. The solution was poured into 1N HCl (5 mL) and extracted with ethyl acetate (3×5 mL), the combined organic extracts washed with brine (1×5 mL) and solvent removed in vacuo to yield crude product which was purified by column chromatography on silica gel (2-4% methanol/chloroform). The pure product was dissolved in 4M HCl in dioxane (2 mL) and stirred at room temperature for 3 hours, solvent removed in vacuo and the crude residue dissolved in dichloromethane (1 mL) and pyridine (68 μL, 0.84 mmol) and methanesulfonyl chloride (26 uL, 0.36 mmol) added and the solution stirred at room temperature for 16 hours. Solvent was removed in vacuo and the crude residue was purified by column chromatography on silica gel (2-4% methanol/chloroform) to give the title compound as a colorless solid; 1H NMR (d6-dmso) δ 13.69(s, 1H), 10.23 (s, 1H), 8.49 (s, 1H), 8.02, 7.99 (d, 1H), 7.65-7.55 (q, 3H), 7.40-7.30 (t, 1H), 7.25-7.15 (q, 2H), 7.06, 7.03 (d, 1H), 6.90, 6.89, 6.88, 6.86 (dd, 1H), 6.36, 6.34 (d, 1H), 3.95 (s, 3H), 3.41 (s, 3H), 3.08 (s, 3H), 2.31-2.18 (m, 1H), 1.96-1.84 (m, 1H), 1.29-1.17 (m, 1H), 0.83-0.69 (m, 1H), 0.69-0.57 (q, 6H), 0.36-0.23 (m, 1H); MS (ESI) m/z 719 (M+H+).

Provenance & Evidence