Hydrochloric Acid → HCID 22380035, compound

HRID 1988706Notes

Reaction equation

HRID 1988706 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([NH:12]C(=O)C)=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[F:29])[CH3:2].Cl>CO>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([NH2:12])=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[F:29])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22379892HCID 22379892, compound

Product 1

HCID 22380035HCID 22380035, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude N-{1-Ethyl-2-{[2-(2,5-difluorophenyl)-1H-imidazol-1-yl]methyl}-1H-benzimidazol-5-yl}acetamide is treated with 10% aqueous HCl (20 mL) in methanol (10 mL) at reflux for 1.5 h. After cooling, the methanol is removed in vacuo, and the aqueous layer washed with ethyl acetate. The aqueous layer is adjusted to pH 10 with 3 N NaOH, then extracted with ethyl acetate (3×), and the combined organic extracts washed with water (2×) then saturated aqueous sodium chloride, dried (MgSO4) and concentrated to give 1-Ethyl-2-{[2-(2,5-difluorophenyl)-1H-imidazol-1-yl]methyl}-5-amino-1H-benzimidazole. LCMS MH+ 354.4.

Workup

  1. temperatureat reflux for 1.5 h
  2. temperatureAfter cooling
  3. customthe methanol is removed in vacuo
  4. washthe aqueous layer washed with ethyl acetate
  5. extractionextracted with ethyl acetate (3×)
  6. washthe combined organic extracts washed with water (2×)
  7. dry with materialsaturated aqueous sodium chloride, dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0207ff0a1fa740f098832d7685cea783
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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