HCID 57291959, compound → HCID 70177973, compound

Participants

Reaction Steps

2-Chloro-5-methoxy-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole (0.320 g, 1.1 mmol) was dissolved in ethanol (15 mL) and isopropylamine (5 mL). The resulting mixture was heated in a sealed tube for three days, after which time it was concentrated in vacuo. The resulting product was purified by flash chromatography (9:0.5:0.5 CH2Cl2:ethyl acetate:methanol) to yield the title compound (18 mg, 5%) as a 1.5:1 mix of regioisomers by 1H NMR; MS (ES): m/z 322 (M+1); 1H NMR (DMSO-d6) δ: 7.13 (d, J=8.5 Hz, 0.4H), 7.03 (d, J=8.5, 0.6H), 6.85 (d, J=2.4 Hz, 0.6H), 6.76 (d, J=2.4 Hz, 0.4H), 6.62 (dd, 0.4H), 6.50 (dd, 0.6H), 5.67 (t, 1H), 5.28-5.19 (m, 1.5H), 4.37 (m, 1H), 3.73 (s, 3H), 1.40 (m, 3H), 1.23 (d, 6H).

Provenance & Evidence