Acetaldehyde → HCID 86676326, compound

HRID 1023023Notes

Reaction equation

HRID 1023023 reaction equation
C(=O)C.[CH3:4][C:5]1[N:9]([CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[S:20][CH:21]=[C:22]([C:24](=[N:26][O:27]CCCCC4C=CC=CC=4)[CH3:25])[N:23]=3)[CH2:15][CH2:14]2)=[O:12])[N:8]=[C:7]([C:38]([F:41])([F:40])[F:39])[CH:6]=1.Cl.NO>CO>[OH:27][N:26]=[C:24]([C:22]1[N:23]=[C:19]([CH:16]2[CH2:17][CH2:18][N:13]([C:11](=[O:12])[CH2:10][N:9]3[C:5]([CH3:4])=[CH:6][C:7]([C:38]([F:41])([F:40])[F:39])=[N:8]3)[CH2:14][CH2:15]2)[S:20][CH:21]=1)[CH3:25]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 86676327HCID 86676327, compound

Product 1

HCID 86676326HCID 86676326, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[4-(4-acetyl-2-thiazolyl)-1-piperidinyl]-2-[5-methyl-3-trifluoromethyl)-1H-pyrazol-1-yl)ethanone (i.e. the product of Example 1, Step D) (4.5 g, 11.25 mmol) and hydroxylamine hydrochloride (0.945 g, 13.5 mmol) in methanol (60 mL) was heated at reflux for 6 h. The reaction mixture was concentrated under reduced pressure and partitioned between saturated sodium bicarbonate and dichloromethane. The organic phase was separated and the aqueous phase was extracted two additional times with dichloromethane. The organic phases were combined, washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated to provide 4.2 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompartitioned between saturated sodium bicarbonate and dichloromethane
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted two additional times with dichloromethane
  7. washwashed with saturated sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-afbb9e05cebe49f894ec90375dce5f7f
Source dataset
uspto-grants-2014_05
Patent number
US08722678B2

Reaction notes

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