Hydrochloric Acid → HCID 90416836, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 98C (0.09 g, 0.26 mmol) in dioxane (5.2 mL) was treated with hydrogen chloride (4M in dioxane) (6.5 mL, 26 mmol) and heated at 75° C. for 30 minutes. The reaction mixture was neutralized with saturated sodium bicarbonate solution. The resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 0 to 20% methanol in dichloromethane). The material was further purified by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-80%) to provide the title compound (0.0066 g, 7.6%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.81 (d, J=4.88 Hz, 1H), 10.38 (s, 1H), 7.41 (m, 2H), 7.12 (t, J=2.75 Hz, 1H), 6.86 (d, J=8.54 Hz, 1H), 6.80 (dd, J=6.71, 5.80 Hz, 1H), 6.37 (dd, J=3.05, 1.83 Hz, 1H), 6.14 (m, 1H), 4.15 (s, 3H), 3.74 (d, J=6.71 Hz, 2H), 1.03 (m, 1H), 0.40 (ddd, J=8.09, 5.95, 4.27 Hz, 2H), 0.15 (ddd, J=5.95, 4.58, 4.43 Hz, 2H). MS (ESI+) m/z 334.1 (M+H)+.

Provenance & Evidence