Dichloromethane → HCID 136387544, compound

Participants

Reaction Steps

To a solution of Example 78c (40.5 mg, 0.110 mmol) and triethylamine (0.077 mL, 0.55 mmol) in the mixture of dichloromethane (2 mL) and tetrahydrofuran (2 mL) was added ethanesulfonyl chloride (0.038 mL, 0.40 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 6 hours and concentrated. The residue was diluted with dioxane (2 mL) and 1M sodium hydroxide (1.1 mL), and heated at 50° C. for 1 hour. The reaction mixture was cooled to ambient temperature, diluted with water and ethyl acetate, adjusted the pH to 7 by addition of 1M HCl and separated. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 1-5% methanol in dichloromethane) to afford the title compound (20 mg, 40%). 1 H NMR (300 MHz, DMSO-d6) δ 12.45 (s, 1 H) 11.45 (s, 1 H) 9.81 (s, 1 H) 8.04 (s, 1 H) 7.36-7.50 (m, 2 H) 7.13-7.27 (m, 2 H) 7.02-7.12 (m, 1 H) 6.88 (d, J=8.73 Hz, 1 H) 3.13 (q, J=7.14 Hz, 2 H) 2.63 (s, 3 H) 1.23 (t, J=7.34 Hz, 3 H). MS (ESI+) m/z 461 (M+H)+.

Provenance & Evidence