Water → HCID 178513729, compound

Participants

Reaction Conditions

Reaction Steps

To the product of Example 42E (200 mg, 0.27 mmol) in concentrated sulfuric acid (4 mL) at 0° C. was added water (0.4 mL) and the mixture was stirred at 0° C. for 10 minutes and at 80° C. for 40 minutes. After cooling to ambient temperature, the mixture was poured into ice-water, adjusted to pH 9 by saturated aqueous sodium carbonate and extracted with dichloromethane. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. 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 13.66 (s, 1H), 11.86 (s, 1H), 9.58 (s, 1H), 8.76 (brs, 2H), 8.63 (s, 1H), 7.83-7.78 (m, 2H), 7.61 (d, J=8.1 Hz, 2H), 7.49-7.43 (m, 2H), 7.01 (d, J=2.4 Hz, 1H), 6.43 (dd, J=9.0, 2.4 Hz, 1H), 4.73 (s, 2H), 3.27 (s, 8H). MS: 530 (M+H+).

Provenance & Evidence