Acetic Acid → HCID 11983443, compound

HRID 2262750Notes

Reaction equation

HRID 2262750 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:6]1[CH:26]=[CH:25][C:9]2[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[CH:14]=3)[CH:11]=[N:12][C:8]=2[CH:7]=1)[CH3:5].C(O)(=O)C.Cl>ClCCl>[CH3:1][O:2][NH:3][CH:4]([C:6]1[CH:26]=[CH:25][C:9]2[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[CH:14]=3)[CH:11]=[N:12][C:8]=2[CH:7]=1)[CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 85040439HCID 85040439, compound

Product 1

HCID 11983443HCID 11983443, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[1-(3-pyridin-3-yl-phenyl)-1H-benzoimidazol-5-yl]-ethanone O-methyl-oxime (prepared as described in WO 96/33191) (0.88 g, 2.57 mmol) in dichloromethane (10 ml) was added pyridine-borane complex (0.87 ml, 8.57 mmol) and glacial acetic acid (2.5 ml), successively. The resultant solution was stirred at reflux in a nitrogen atmosphere for 4 days. Hydrochloric acid (5 ml, 1M) was added to the cooled solution and stirring was continued for 30 min and the resultant mixture was concentrated in vacuo. The concentrate was partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer was dried over sodium sulphate and eluted through silica gel with a mixture of ethyl acetate and methanol (9:1 v/v). This afforded 27 mg of the desired product. LC-ESI-HRMS of [M+H]+ shows 345.1717 Da. Calc. 345.171536 Da. dev. 0.5 ppm.

Workup

  1. temperatureat reflux in a nitrogen atmosphere for 4 days
  2. concentrationthe resultant mixture was concentrated in vacuo
  3. customThe concentrate was partitioned between ethyl acetate and aqueous sodium bicarbonate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. washeluted through silica gel with a mixture of ethyl acetate and methanol (9:1 v/v)

Sources & evidence

ORD record
ord-ec77c417d973426987cf4cbdc06782a7
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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