Isopropylamine → HCID 70179502, compound

Participants

Reaction Steps

A mixture of 2-bromo-6-chloro-1-(2,3-di-O-acetyl-5-deoxy-β-D-ribofuranosyl)-1H-benzimidazole and 10 mL of isopropylamine in 5 mL of absolute ethanol was refluxed for 18 h. To this resultant mixture was added 1 mL of 1N NaOH and the resultant solution was dry-packed in silica gel. Flash column chromatography on silica gel with EtOAc/hexane (1:1) gave 0.15 g of a still impure product. Further purification on a silica gel preparative plate using EtOAc/hexane (1:1) gave 0.06 g (28%) of the title compound as a foam. 1H NMR (DMSO-d6) δ1.18 (d, 6H, 2×CH3), 1.35 (d, 3H, CH3), 3.7-3.8 (m, 1H, CH), 3.8-3.9 (m, 1H, CH), 4 (sextet, 1H, CH), 4.3 (q, 1H, CH), 5.2-5.21 (m, 2H, 2×OH), 5.61 (d, 1H, CH), 6.38 (d, 1H, aromatic), 6.95 (d, 1H, aromatic), 7.1-7.2 (m, 2H, aromatic & NH).

Provenance & Evidence