Ethanol → HCID 54228188, compound

Temperature

80 °C

Aniline (5 ml ) and 2-bromo-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole (0.6 g, 1.1 mmol) were combined with absolute ethanol (35 mL) and stirred at 80° C. for 14 days. The reaction mixture was concentrated and the aniline was distilled off under high vacuum at 80° C. The brown residue was dissolved in methanol (50 mL) and K2CO3 was added. This solution was stirred for 18 h. The solution was filtered, concentrated and purified on a silica gel column (2.5 cm×16 cm, 230-400 mesh) with 1:15 methanol:dichloromethane to give a white solid (0.024 g, 0.06 mmol, 5%). MS (AP+): m/z (rel. intensity) 410 (19.39, M+1); 1H NMR (DMSO-d6) d 9.09 (s, 1H, NH), 7.83 (s, 1H, Ar—H), 7.78 (d, 1H, Ar—H, J=7.9 Hz), 7.58 (s, 2H, Ar—H), 7.31 (t, 2H, Ar—H, J=7.9 Hz), 6.99 (t, 1H, Ar—H, J=7.5 Hz), 5.95 (d, 1H, H-1′, J=7.8 Hz), 5.86 (t, 1H, OH, J=4.4 Hz), 5.38 (d, 1H, OH, J=7.6 Hz), 5.30 (d, 1H, OH, J=4.2 Hz), 4.33 (apparent dd, 1H, H-4′, J=13.4 Hz, J=7.8 Hz), 4.11 (apparent t, 1H, H-2′, J=4.8 Hz), 4.05 (s, 1H, H-4′), 3.79-3.71 (m, 2H, H-5′).

1. concentrationThe reaction mixture was concentrated
2. distillationthe aniline was distilled off under high vacuum at 80° C
3. dissolutionThe brown residue was dissolved in methanol (50 mL)
4. additionK2CO3 was added
5. stirringThis solution was stirred for 18 h
6. filtrationThe solution was filtered
7. concentrationconcentrated
8. custompurified on a silica gel column (2.5 cm×16 cm, 230-400 mesh) with 1:15 methanol

ORD record

ord-fac69f7883604dad9c1d8998a11b70db

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06307043B1