Ethanol → HCID 117728077, compound

Participants

Reaction Steps

Compound 82d (108 mg, 0.246 mmol) was treated with 5 mL of DCM-TFA-water (30:10:1) and stirred at room temperature for 1 h. EtOH (1 mL) was added and the mixture was concentrated to a pale yellow resin. The resulting material in DCM (10 mL) was treated with solid NaHCO3 (2 g), stirred 20 min, filtered, and concentrated to give a white solid which was purified by flash column chromatography on silica gel (0-25% MeOH-EtOAc) to afford a white solid. A portion (68.1 mg) of this material in MeOH (70 mL) and CHCl3 (20 mL) was treated with DIEA (229 μL, 1.32 mmol), refluxed for 2.5 h, and then concentrated to give a white solid which was purified by flash column chromatography on silica gel (0-25% MeOH-EtOAc) to afford the title compound 65 as a white solid. 1H-NMR (CDCl3-MeOH (3:1), 400 MHz): δ 8.15 (d, J=8.6 Hz, 1H), 8.02 (d, J=8.6 Hz, 1H), 7.92 (s, 1H), 7.84 (d, J=8.3 Hz, 1H), 7.73 (ddd, J=8.4, 7.0, 1.5 Hz, 1H), 7.67-7.70 (m, 2H), 7.58-7.63 (m, 2H), 7.52-7.58 (m, 1H), 7.36-7.40 (m, 2H), 7.29 (s, 1H), 4.12-4.17 (m, 4H), 3.81-3.86 (m, 4H), 3.38-3.44 (m, 2H), 3.27-3.33 ppm (m, 2H). Mass spectrum (LCMS, ESI pos.): Calcd. for C29H26N8O2, 519.2 (M+H). found 519.0.

Provenance & Evidence