Water → HCID 178513730, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Example 18C (100 mg, 0.14 mmol) in concentrated sulfuric acid (5 mL) was added water (1 mL) at 0° C. and the mixture was heated at 95° C. for 20 minutes. After cooling to ambient temperature, water (3 mL) was added, and the mixture was adjusted to pH 8-9 with saturated aqueous sodium bicarbonate and extracted with dichloromethane (3×20 mL). The combined organic phase was concentrated and the residue was purified by preparative HPLC using a gradient of 10/90 to 75/25 acetonitrile in water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 13.62 (s, 1 H), 11.85 (s, 1 H), 9.62 (s, 1 H), 8.69 (s, 2 H), 8.61 (s, 1 H), 7.85 (br, 1 H), 7.58 (m, 1 H), 7.55 (m, 1 H), 7.52 (d, J=2.4 Hz, 1 H), 7.42-7.37 (m, 1 H), 7.15 (dd, J=9, 2.4 Hz, 1 H), 6.85 (d, J=9 Hz, 1 H), 4.74 (s, 2 H), 3.27 (m, 4 H), 2.08-1.70 (m, 4 H). MS: 530 (M+H+).

Provenance & Evidence