Sodium Bicarbonate → HCID 178491941, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Example 49C (80 mg, 0.13 mmol) in concentrated sulfuric acid (5 mL) at 0° C. was added water (1 mL) and the mixture was heated to 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 12.00 (br, 1 H), 9.68 (br, 1 H), 8.62 (s, 1 H), 7.85 (d, J=8.4 Hz, 1 H), 7.73 (s, 1 H), 7.61-7.58 (m, 2 H), 7.48-7.42 (m, 1 H), 7.08 (d, J=1.2 Hz, 1 H), 6.62-6.58 (dd, J=8.4, 1.2 Hz, 1 H), 4.75 (s, 2 H), 4.23 (d, 2 H), 3.88 (s, 3 H), 3.44-3.41 (m, 8 H). MS: 525 (M+H+).

Provenance & Evidence