Hydrochloric Acid → HCID 178477708, compound

Participants

Reaction Steps

A mixture of Example 82d (0.09 g, 0.262 mmol) in dichloroethane (2 mL) and 1,4-dioxane (4 mL) was treated with ethanesulfonyl chloride (0.075 mL, 0.786 mmol) and triethylamine (0.183 mL, 1.31 mmol). The mixture was stirred at ambient temperature overnight and then concentrated. The mixture was redissolved in 1,4-dioxane (4 mL), treated with sodium hydroxide solution (4 M aqueous) (0.655 ml, 2.62 mmol) and heated at 50° C. for 1.75 hours. The mixture was then cooled to ambient temperature and neutralized with hydrochloric acid solution (2 M aqueous). The mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (2×60 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by reverse phase HPLC(C18, acetonitrile/water (0.1% TFA), 10-60%) to provide 0.0477 g (33%) of the title compound as the TFA salt. 1H NMR (400 MHz, DMSO-d6) δ 10.48 (s, 1H), 9.56 (s, 1H), 7.98 (dd, J=5.19, 1.22 Hz, 1H), 7.64 (d, J=2.44 Hz, 1H), 7.58 (s, 1H), 7.41 (m, 1H), 7.27 (d, J=8.54 Hz, 1H), 7.13 (dd, J=8.54, 2.44 Hz, 1H), 6.90 (s, 1H), 6.60 (dd, J=6.56, 5.65 Hz, 1H), 6.42 (d, J=8.85 Hz, 1H), 5.53 (s, 1H), 4.08 (s, 3H), 3.97 (s, 1H), 3.19 (q, J=7.32 Hz, 2H), 1.29 (t, J=7.32 Hz, 3H). MS (ESI+) m/z 436.2 (M+H)+.

Provenance & Evidence