Ethanol → HCID 54067789, compound

HRID 1421474Notes

Reaction equation

HRID 1421474 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].Br[C:7]1[N:11]([C@H:12]2[O:24][C@@H:23]([CH2:25][O:26]C(=O)C)[C@H:18]([O:19]C(=O)C)[C@@H:13]2[O:14]C(=O)C)[C:10]2[CH:30]=[C:31]([Cl:35])[C:32]([Cl:34])=[CH:33][C:9]=2[N:8]=1.C(O)C>CN(C=O)C>[Cl:34][C:32]1[C:31]([Cl:35])=[CH:30][C:10]2[N:11]([C@H:12]3[O:24][C@@H:23]([CH2:25][OH:26])[C@H:18]([OH:19])[C@@H:13]3[OH:14])[C:7]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[N:8][C:9]=2[CH:33]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6558IsobutylamineHCID 54518783HCID 54518783, compound

Product 1

HCID 54067789HCID 54067789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Isobutylamine (10 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 (50 mL) and stirred at 75° C. for 24 h. The reaction mixture was concentrated and purified on a silica gel column (2.5 cm×16 cm, 230-400 mesh) with 1:20 methanol:dichloromethane (500 mL), then 1:9 methanol:dichloromethane to give a tan solid (0.39 g, 1.0 mmol. 90%); m.p. 136° C.; [a]20D =(-) 28.4 (c=0.5 DMF).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified on a silica gel column (2.5 cm×16 cm, 230-400 mesh) with 1:20 methanol
  3. customdichloromethane (500 mL), then 1:9 methanol:dichloromethane to give a tan solid (0.39 g, 1.0 mmol. 90%)

Sources & evidence

ORD record
ord-65db769cd07c4191ae4f692aaa341c09
Source dataset
uspto-grants-2000_06
Patent number
US06077832

Reaction notes

Loading…