Hydrochloric Acid → HCID 118023544, compound

HRID 929310Notes

Reaction equation

HRID 929310 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:15][CH3:16])[C:8](=[O:14])[CH2:9][CH2:10][C:11](=O)[CH3:12])=[CH:5][N:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1.C([O-])(=O)C.[Na+].[NH2:28][OH:29].Cl>C1COCC1.O.CCOC(C)=O>[Cl:1][C:2]1[C:6]([N:7]([CH2:15][CH3:16])[C:8](=[O:14])[CH2:9][CH2:10]/[C:11](=[N:28]/[OH:29])/[CH3:12])=[CH:5][N:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 517045Sodium AcetateHCID 69262205HCID 69262205, compound

Product 1

HCID 118023544HCID 118023544, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-4-oxo pentanamide (0.10 g, 0.31 mmol) in THF (3.0 mL) was added a solution of sodium acetate (0.064 g, 0.78 mmol) and hydroxylamine.HCl salt (0.033 g, 0.47 mmol) in water (0.5 mL), and the mixture stirred for one hour. The mixture was diluted with EtOAc and water. The organic phase was separated, and the aqueous extracted with EtOAc. The combined organic phase was washed with brine, dried over MgSO4, and filtered. Removal of the volatiles under reduced pressure gave colorless gum, which was purified on silica gel eluting with MeOH/CH2Cl2 to give the title compound F105 as a colorless gum (0.088 g, 80%).

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous extracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customRemoval of the volatiles under reduced pressure
  7. customgave colorless gum, which
  8. customwas purified on silica gel eluting with MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a793c76161d3402c967a48b39009c54c
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

Loading…