Ethanol → HCID 53851174, compound

HRID 1167076Notes

Reaction equation

[CH:1]([NH2:4])([CH3:3])[CH3:2].Br[C:6]1[N:10]([C@H:11]2[O:17][C@@H:16]([CH3:18])[C@:14](C(=O)C)([OH:15])[C@:12]2(C(=O)C)[OH:13])[C:9]2[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:8]=2[N:7]=1.C(O)C>CN(C=O)C>[CH:1]([NH:4][C:6]1[N:10]([C@H:11]2[O:17][C@@H:16]([CH3:18])[C@H:14]([OH:15])[C@@H:12]2[OH:13])[C:9]2[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:8]=2[N:7]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Isopropylamine (5 mL ) and 2-bromo-5,6-dichloro-1-(5-deoxy-2,3-diacetyl-beta-L-ribofuranosyl)-1H-benzimidazole (0.40 g, 0.86 mmol) were combined with absolute ethanol (20 mL) and stirred at 80° C. for 24 h. The reaction mixture was concentrated and purified by multiple cyclings on a chromatotron fitted with a 2 mm silica gel rotor, with 1:30 methanol:dichloromethane and 1:1 ethyl acetate:hexanes and 1:4 acetone:dichloromethane to give a white solid (0.18 g, 0.70, mmol, 60%); m.p. 103-105° C.; [α]20D=(+) 38.8 (c=0.5 DMF); UV λmax (ε): pH 7.0:303 nm (10,400), 276 (2,500), 260 (10,000); MS (CI): m/z (rel. intensity) 360 (14.26, M−); 1H NMR (DMSO-d6) d 7.39 (s, 1H, Ar—H), 7.31 (s, 1H, Ar—H), 6.57 (d, 1H, NH, J=7.6 Hz), 5.68 (d, 1H, H-1′, J=6.6 Hz), 5.23 (d, 1H, OH, J=4.8 Hz), 5.21 (d, 1H, OH, J=7.1 Hz), 4.31 (q, 1H, H-4′, J=6.7 Hz), 4.04-3.98 (m, 1H, isopropyl-CH), 3.95-3.87 (m, 1H), 3.81-3.76 (m, 1H), 1.36 (d, 3H, H-5′, J=6.5 Hz), 1.20 (d, 6H, cyclopentyl-CH2, J=6.6 Hz).

Workup

concentrationThe reaction mixture was concentrated
custompurified by multiple cyclings on a chromatotron
customfitted with a 2 mm silica gel rotor, with 1:30 methanol
customdichloromethane and 1:1 ethyl acetate:hexanes and 1:4 acetone:dichloromethane to give a white solid (0.18 g, 0.70, mmol, 60%)

Sources & evidence

ORD record: ord-c6e93f158b174ff999486be09e6494bb
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617315B1

Reaction notes

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