Water → HCID 77844702, compound

Participants

Reaction Steps

To a solution of 121h (150 mg, 0.22 mmol) in methanol (10 mL) was added NaBH4 (41.8 mg, 1.1 mmol) at room temperature. After the reaction was stirred for 1 h, LCMS indicated the reaction was complete. The mixture was poured into water (30 mL) and concentrated under reduced pressure. The residue was extracted with dichloromethane (3×30 mL). The combined organic layer was washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue solid was purified by prep-HPLC to afford 121 (60.3 mg, 40%) as white solid. MS: [M+H]+ 680. 1H NMR (500 MHz, DMSO-d6) δ 8.63 (d, J=2.0 Hz, 1H), 8.51 (s, 1H), 7.90 (d, J=3.0 Hz, 1H), 7.41 (m, 2H), 7.31-7.23 (m, 4H), 6.78 (d, J=1.0 Hz, 2H), 4.80 (m, 1H), 4.55-4.54 (m, 2H), 4.49-4.4.48 (m, 2H), 4.28-4.20 (m, 2H), 3.69-3.64 (m, 1H), 3.60 (s, 3H), 3.29-3.27 (m, 2H), 2.89-2.88 (m, 1H), 2.75-2.67 (m, 4H), 2.61 (m, 2H), 1.93-1.86 (m, 3H), 1.59 (m, 2H), 0.85-0.81 (m, 6H).

Provenance & Evidence