Triethylamine → HCID 135567317, compound

Participants

Reaction Steps

To a solution of Example 74f (0.05 g, 0.150 mmol) and triethylamine (0.084 mL, 0.602 mmol) in dichloromethane (1.504 mL) and tetrahydrofuran (1.504 mL) was added drop-wise ethanesulfonyl chloride (0.046 mL, 0.481 mmol). The reaction mixture was stirred for three hours at ambient temperature and concentrated. The residue was diluted with dioxane (3 mL) and 1 M sodium hydroxide (1 mL) and heated at 60° C. for 1 hour. The mixture was cooled and diluted with water and ethyl acetate adjusting the pH to 6 with 1 M HCl. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated. Purification by chromatography (silica gel, 1-5% methanol in dichloromethane) afforded the title compound (0.03 g, 45%). 1H NMR (300 MHz, DMSO-d6) δ 12.43 (s, 1H), 11.41 (s, 1H), 9.83 (s, 1H), 8.04 (s, 1H), 7.43 (d, J=2.71 Hz, 1H), 7.26-7.33 (m, 2H), 7.22 (dd, J=8.82, 2.71 Hz, 1H), 7.00-7.08 (m, 2H), 6.90 (d, J=7.46 Hz, 2H), 3.15 (q, J=7.23 Hz, 2H), 2.59 (s, 3H), 1.24 (t, J=7.46 Hz, 3H). MS (ESI+) m/z 425 [M+H]+.

Provenance & Evidence