Sodium Acetate → HCID 178502636, compound

HRID 1093817Notes

Reaction equation

HRID 1093817 reaction equation
Cl.[CH3:2][O:3][NH2:4].[CH:5]([C:7]1[CH:36]=[CH:35][CH:34]=[CH:33][C:8]=1[O:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:32])[CH2:17][NH:18][C:19]([C:21]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:23][N:22]=2)=[O:20])[CH2:12][CH2:11]1)=O.C([O-])(=O)C.[Na+]>CO.O>[CH3:2][O:3][N:4]=[CH:5][C:7]1[CH:36]=[CH:35][CH:34]=[CH:33][C:8]=1[O:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:32])[CH2:17][NH:18][C:19]([C:21]2[CH:25]=[C:24]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:23][N:22]=2)=[O:20])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 178519541HCID 178519541, compound

Product 1

HCID 178502636HCID 178502636, compoundYield 31.13%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

O-Methyl-hydroxylamine hydrochloride (23 mg, 0.27 mmol) was added to a stirred cold (0° C.) mixture of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-formyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide (100 mg, 0.23 mmol) and sodium acetate (56 mg, 0.7 mmol) in MeOH (10 mL) and stirring was continued at ambient temperature for 4 hrs. The reaction mixture was diluted with water, extracted with ethyl acetate, dried over sodium sulfate, and the organic layer was concentrated under reduced pressure. The residue was purified by preparative HPLC to afford 33 mg (31.13% yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid (2-{4-[2-(methoxyimino-methyl)-phenoxy]-piperidin-1-yl}-2-oxo-ethyl)-amide. LC/MS [M+H]+: 462.2, 96.3%. 1H NMR (300 MHz, DMSO-d6): δ13.7 (s, 1H), 8.4 (s, 1H), 8.1 (t, 1H), 7.8 (t, 2H), 7.7 (d, 1H), 7.5-7.34 (m, 4H), 7.2 (d, 1H), 7.1 (s, 1H), 7.0 (t, 1H), 4.8 (bs, 1H), 4.2 (b, 2H), 3.9 (s, 3H), 3.8-3.6 (bs, 2H), 3.5 (b, 2H), 2.1-1.9 (b, 2H), 1.8-1.6 (b, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-bb46262b1cab4b139c24925f2952d0b8
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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