Sodium Acetate → HCID 73884807, compound

HRID 1594049Notes

Reaction equation

HRID 1594049 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12](=O)[CH3:13])=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:15][C:16]1[N:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:18]=[CH:19][CH:20]=1)[CH3:2].Cl.[O:29]([NH2:31])[CH3:30].C([O-])(=O)C.[Na+]>CO>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12](=[N:31][O:29][CH3:30])[CH3:13])=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:15][C:16]1[N:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:18]=[CH:19][CH:20]=1)[CH3:2]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 22380334HCID 22380334, compound

Product 1

HCID 73884807HCID 73884807, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-Ethyl-2-{[2-(3-fluorophenyl)-pyrazol-3-yl]methyl}-5-acetyl-1H-benzimidazole (23 mg), methoxylamine hydrochloride (15 mg, 3 eq.), and sodium acetate (15 mg, 3 eq.) in methanol (1 mL) is stirred at room temperature overnight. The solvent is removed in vacuo and aqueous sodium bicarbonate added to pH 9, then extracted with ethyl acetate. The organic layer is dried (Na2SO4) and concentrated to give 1-Ethyl-2-{[2-(3-fluorophenyl)-pyrazol-3-yl]methyl}-5-[1-(methoxyimino)ethyl]-1H-benzimidazole. 1H NMR (CDCl3): δ 7.94 (d, 1H); 7.73 (dd, 1H); 7.73 (dd, 1H); 7.63 (d, 1H); 7.52 (m, 1H); 7.38-7.40 (m, 3H); 7.27 (m, 1H); 6.19 (d, 1H); 4.32 (s, 2H); 3.87-4.10 (m, 5H); 2.30 (s, 3H); 1.22 (t, 3H).

Workup

  1. customThe solvent is removed in vacuo and aqueous sodium bicarbonate
  2. additionadded to pH 9
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-48a78031352c4e599b3b52fcc7b26dfb
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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