Water → HCID 178513728, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Example 22B (150 mg, 0.2 mmol) in concentrated sulfuric acid (5 mL) was added water (1 mL) at 0° C. and the mixture was stirred at 95° C. for 20 minutes. After cooling to ambient temperature, water (3 mL) was added. The mixture was adjusted to pH 8-9 with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (3×20 mL). The organic layers were concentrated and the residue was purified by preparative HPLC using a gradient of 10/90 to 80/20 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 13.51 (br, 1 H), 11.64 (s, 1 H), 9.52 (br, 1 H), 8.80 (s, 2 H), 8.61(s, 1 H), 7.81 (s, 1-H), 7.62 (d, J=9 Hz, 1 H), 7.56-7.53 (m, 2 H), 7.43-7.41 (m, 1 H), 7.07 (d, J=2.1 Hz, 1 H), 6.72 (dd, J=9, 2.1 Hz, 1 H), 4.83 (s, 2H), 2.75-2.67 (m, 8 H). MS: 564 (M+H+).

Provenance & Evidence