Sodium Bicarbonate → HCID 178493692, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Example 52D (130 mg, 0.17 mmol) in concentrated sulfuric acid (5 mL) at 0° C. was added water (1 mL) and the mixture was heated at 95° C. for 20 minutes. After cooling to ambient temperature, the mixture was diluted with water (3 mL), adjusted to pH 8-9 with saturated sodium bicarbonate solution 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 80/20 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 12.35 (s, 1 H), 9.61 (s, 1 H), 8.97 (s, 2 H), 8.66 (s, 1 H), 7.91 (s, 1 H), 7.74-7.66 (m 1 H), 7.56-7.53 (m, 2 H), 7.43-7.37 (m, 1 H), 4.77 (s, 2 H), 3.82 (s, 3 H), 3.21 (m, 8 H). MS: 562 (M+H+).

Provenance & Evidence