Sodium Hydroxide → HCID 86271488, compound

Participants

Reaction Steps

To a solution of Example 71 (60 mg, 0.127 mmol) in 5 mL dioxane was added 6 M sodium hydroxide (212 μL, 1.270 mmol). The reaction mixture was held at 50° C. for 12 hours and then diluted with 25 mL water. The aqueous mixture was extracted with ethyl acetate (2×), and the organic fractions were discarded. The aqueous layer was diluted with an equal amount of ethyl acetate and made slightly acidic with 2.5 M hydrochloric acid. The aqueous layer was extracted with ethyl acetate (2×), and the combined organic fractions were washed with brine, dried over magnesium sulfate and concentrated to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 12.20 (s, 1H) 8.76 (s, 1H) 7.92 (d, J=7.93 Hz, 2H) 7.47 (d, J=8.24 Hz, 2H) 7.28-7.39 (m, 2H) 7.15-7.27 (m, 1H) 6.54 (s, 1H) 6.28 (d, J=1.53 Hz, 1H) 3.78 (s, 3H) 3.68 (s, 2H) 3.14 (s, 2H) 2.65 (t, J=5.49 Hz, 2H) 2.50 (s, 3H). MS (ESI+) m/z 459.1 (M+H)+.

Provenance & Evidence