Sodium Bicarbonate → HCID 178492648, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Example 39D (100 mg, 0.13 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, 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 via preparative HPLC using a gradient of 10/90 to 75/25 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 12.18 (s, 1 H), 9.60 (br, 1 H), 8.86 (s, 2 H), 8.64 (s, 1 H), 7.79-7.78 (m, 1 H), 7.77 (s, 1H), 7.72 (s, 1 H), 7.64-7.61 (m, 2 H), 7.48 (d, J=9 Hz, 1 H), 6.98 (s, 1 H), 6.57 (d, J=9 Hz, 1 H), 4.90 (s, 2 H), 3.88 (s, 3 H), 3.23-3.10 (m, 8 H). MS: 554 (M+H+).

Provenance & Evidence