Triethylamine → HCID 178477709, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 69e (0.04 g, 0.106 mmol), ethanesulfonyl chloride (0.054 g, 0.2423 mmol), and triethylamine (0.064 g, 0.635 mmol) in dichloromethane (3 mL) was stirred at ambient temperature for 2 hours. The solvent was removed, and the residue was treated with dioxane (3 mL) and 2.0 N NaOH (2 mL). The reaction mixture was heated at 90° C. for 2 hours. The solvents were partially removed, and the residue was partitioned between water and ethyl acetate. The aqueous layer was neutralized with 10% HCl and extracted with additional ethyl acetate twice. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC(C18, CH3CN/water (0.1% TFA), 0-100%) to afford 0.035 g (56.6%) of the title compound as the TFA salt. 1H NMR (500 MHz, DMSO-d6) δ 10.87 (d, J=5.8, 1H), 10.15 (s, 1H), 8.17 (d, J=2.75 Hz, 1H), 8.00 (d, J=2.75 Hz, 1H), 7.82 (s, 1H), 7.09 (d, J=5.8 Hz, 1H), 7.03-7.07 (m, 2H), 6.58-6.62 (m, 2H), 4.62 (s, 2H), 4.07 (s, 3H), 3.26 (q, J=7.32 Hz, 2H), 1.29 (t, J=7.32 Hz, 3H). MS (DCI+) m/z 470.1 (M+H)+.

Provenance & Evidence