Ethanol → HCID 16057516, compound

HRID 381644Notes

Reaction equation

HRID 381644 reaction equation
Cl.CN.[CH2:4]([N:6](CC)CC)C.Br[C:12]1[N:16]([C@H:17]2[O:29][C@@H:28]([CH2:30][O:31]C(=O)C)[C@H:23]([O:24]C(=O)C)[C@@H:18]2[O:19]C(=O)C)[C:15]2[CH:35]=[C:36]([Cl:40])[C:37]([Cl:39])=[CH:38][C:14]=2[N:13]=1.C(O)C>CN(C=O)C>[Cl:39][C:37]1[C:36]([Cl:40])=[CH:35][C:15]2[N:16]([C@H:17]3[O:29][C@@H:28]([CH2:30][OH:31])[C@H:23]([OH:24])[C@@H:18]3[OH:19])[C:12]([NH:6][CH3:4])=[N:13][C:14]=2[CH:38]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 54518783HCID 54518783, compound

Product 1

HCID 16057516HCID 16057516, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methylamine hydrochloride (3.0 g, 45 mmol), triethylamine (3 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 (25 mL) and stirred at 80° C. for 24 h. The reaction mixture was separated between saturated sodium bicarbonate (50 mL) and ethyl acetate (150 mL). The organic layer was dried with sodium sulfate, concentrated and absorbed onto silica gel (15 g). This material was dry loaded onto a silica gel column (5 cm×10 cm, 230-400 mesh) with 1:10 methanol:dichloromethane. The main product came off the column as a white solid (0.22 g, 0.62 mmol, 54%) m.p. 238-240° C.; [a]20D=(−) 15.2 (c=0.5 DMF).

Workup

  1. customThe reaction mixture was separated between saturated sodium bicarbonate (50 mL) and ethyl acetate (150 mL)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. concentrationconcentrated
  4. customabsorbed onto silica gel (15 g)
  5. customThis material was dry

Sources & evidence

ORD record
ord-d3daeb4ad3ef4bebbb09366439179fad
Source dataset
uspto-grants-2001_10
Patent number
US06307043B1

Reaction notes

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