Hydrochloric Acid → HCID 90417505, compound

Participants

Reaction Steps

A mixture of Example 17C (0.1 g, 0.299 mmol), 3,4-difluorophenol (0.058 g, 0.449 mmol) and Cs2CO3 (0.146 g, 0.449 mmol) in DMSO (5 mL) was stirred at 110° C. for 12 hours, cooled and partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated. The resulting residue (0.13 g, 0.405 mmol) and 4M HCl in dioxane (4 M, 13 mL) was heated at 70° C. for 12 hours, cooled and concentrated. The residue was purified by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-100%) to afford the title compound (0.05 g, 0.116 mmol, 38.7%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.00 (d, J=5.3 Hz, 1H), 8.01 (d, J=2.4 Hz, 1H), 7.80 (dd, J=8.7, 2.4 Hz, 1H), 7.68 (s, 1H), 7.50 (dd, J=19.6, 9.2 Hz, 1H), 7.40 (ddd, J=11.5, 6.8, 2.9 Hz, 1H), 7.11 (d, J=8.6 Hz, 1H), 7.00 (d, J=7.7 Hz, 1H), 6.95-6.88 (m, 1H), 6.54 (d, J=6.3 Hz, 1H), 4.11 (s, 3H), 3.26 (s, 3H). MS (ESI+) m/z 431.0 (M+H)+.

Provenance & Evidence