Hydroxyamine hydrochloride → HCID 178523499, compound

HRID 1093814Notes

Reaction equation

HRID 1093814 reaction equation
Cl.NO.[CH:4]([C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:31])[CH2:16][NH:17][C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:22][N:21]=2)=[O:19])[CH2:11][CH2:10]1)=[O:5].C([O-])(=O)C.[Na+]>CO.O>[OH:5][CH2:4][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:31])[CH2:16][NH:17][C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:22][N:21]=2)=[O:19])[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 178519541HCID 178519541, compound

Product 1

HCID 178523499HCID 178523499, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (33 mg, 0.5 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 (150 mg, 0.4 mmol) and sodium acetate (65 mg, 0.8 mmol) in MeOH (3 mL) and stirring was continued at ambient temperature for 4 hrs. The reaction mixture was diluted with water, extracted with ethyl acetate and dried over sodium sulfate. The organic layer was concentrated under reduced pressure to afford 25 mg (58% yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-hydroxymethyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 435.2, 93.8%, 1H NMR (300 MHz, DMSO-d6): δ8.3 (s, 1H), 8.2 (b, 1H), 7.8 (d, 2H), 7.7 (d, 1H), 7.5 (t, 2H), 7.4 (t, 2H), 7.2 (d, 2H), 7.0 (t, 1H), 4.8 (m, 1H), 4.2 (m, 2H), 3.8 (m, 2H), 3.5 (m, 2H), 2.0 (m, 2H), 1.8 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5fd710d7c2c14e80b7f85626c39ef2bc
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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