Ethanol → HCID 136310633, compound

Participants

Reaction Steps

Compound 84e (89.8 mg, 0.138 mmol) was treated with 5 mL of DCM-TFA-water (30:10:1) and stirred at rt for 14 h. EtOH (1 mL) was added and the mixture was concentrated to a yellow resin (112 mg). The resulting material was taken up in MeOH (20 mL) and CHCl3 (10 mL), treated with DIEA (241 μL, 1.38 mmol), refluxed for 2 h, and then concentrated to give a beige solid. The solid was then purified by flash column chromatography on silica gel (100% EtOAc, followed by 0-30% MeOH-EtOAc) to afford a beige solid that was washed with MeOH (1.5 mL) and dried to give compound 21 as an off-white solid. 1H-NMR (CDCl3—CD3OD (1:1), 400 MHz): δ 8.19 (d, J=8.6 Hz, 1H), 8.05 (d, J=8.6 Hz, 2H), 8.00 (d, J=8.1 Hz, 1H), 7.87 (d, J=9.1 Hz, 1H), 7.81 (s, 1H), 7.72-7.77 (m, 1H), 7.54-7.59 (m, 1H), 7.52 (d, J=9.1 Hz, 2H), 7.38-7.42 (m, 2H), 7.28 (s, 1H), 4.06-4.10 (m, 4H), 3.81-3.85 (m, 4H), 3.38-3.44 (m, 2H), 3.29-3.33 (m, 2H); Mass spectrum (LCMS, ESI pos.): Calcd. for C29H26N8O2, 519.2 (M+H). found 519.4.

Provenance & Evidence