Hydrochloric Acid → HCID 53482225, compound

Participants

Reaction Steps

To a solution of 186 (0.19 g, 0.26 mmol) in acetic acid (10 mL) was added aqueous HCl (3M, 1.0 mL, 3.0 mmol). The mixture was stirred at room temperature for 3 h then partially concentrated. The residue was partitioned between ethyl acetate and water, the organic phase was collected, washed with saturated aqueous sodium bicarbonate and brine. It was then dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (eluent 15% methanol/chloroform) to give title compound 187 (80 mg, 49% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.53 (d, J=5.5, 1H), 8.50 (d, J=1.6, 1H), 8.30 (s, 1H), 8.18 (d, J=7.8, 1H), 8.04 (dd, J=11.2, 1.6, 1H), 7.89 (dd, J=8.2, 2.2, 1H), 7.54-7.50 (m, 2H), 7.40-7.35 (m, 2H), 7.22-7.15 (m, 2H), 6.67 (d, J=5.5, 1H), 3.83 (s, 2H), 3.40 (s, 2H), 3.37 (t, J=5.7, 2H), 3.22 (s, 3H), 2.82-2.75 (m, 4H), 2.69 (t, J=5.7, 2H). LRMS (M+H): 634.4

Provenance & Evidence