Hydroxyamine hydrochloride → HCID 59101525, compound

HRID 988711Notes

Reaction equation

HRID 988711 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:24]2)=[O:22])=[C:8]([CH:19]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][N:13]=1)=[O:10])(=O)[CH3:2].C([O-])(=O)C.[Na+].Cl.[NH2:38][OH:39]>CO>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:19]=[C:4]([C:1](=[N:38][OH:39])[CH3:2])[CH:5]=[CH:6][C:7]=2[NH:20][C:21]([CH:23]2[CH2:24][CH2:25][N:26]([CH:29]([CH3:30])[CH3:31])[CH2:27][CH2:28]2)=[O:22])=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 21906177HCID 21906177, compound

Product 1

HCID 59101525HCID 59101525, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 5-acetyl-N-(5-chloropyridin-2-yl)-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]benzamide (0.25 g, 0.56 mmol) in methanol (2 mL) was added sodium acetate (0.1 g, 1.2 mmol) followed by hydroxylamine hydrochloride (46 mg, 0.67 mmol). The mixture was stirred overnight at room temperature and concentrated in vacuo. The resulting residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate, and the layers separated. The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by chromatography over silica gel, eluting with 3% 2 M ammonia/methanol solution in dichloromethane to give 0.22 g (85%) of a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. customthe layers separated
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography over silica gel
  8. washeluting with 3% 2 M ammonia/methanol solution in dichloromethane

Sources & evidence

ORD record
ord-0517220f78f44b0799870ba081ce6f39
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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