Ammonium Acetate → HCID 24852674, compound

HRID 599567Notes

Reaction equation

HRID 599567 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:15]=[C:16]2/[C:17](=O)[N:18]([CH2:22][C:23](=O)[C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH2:19][CH2:20][CH2:21]/2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.C([O-])(=O)C.[NH4+:36]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:15]=[C:16]2/[C:17]3[N:18]([CH:22]=[C:23]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[N:36]=3)[CH2:19][CH2:20][CH2:21]/2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 67067247HCID 67067247, compound

Product 1

HCID 24852674HCID 24852674, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}-1-(2-oxo-2-pyridin-4-ylethyl)piperidin-2-one (150 mg) and ammonium acetate (555 mg) in acetic acid (2 mL) was stirred at 120° C. for five hours. The reaction solution was left to cool to room temperature and concentrated under reduced pressure. Ethyl acetate and saturated sodium bicarbonate water were added to the residue, and the organic layer was separated. The resulting organic layer was washed with brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane-ethyl acetate system→ethyl acetate-2-propanol) to obtain 121.5 mg of the title compound. The property values of the compound are as follows.

Workup

  1. waitThe reaction solution was left
  2. concentrationconcentrated under reduced pressure
  3. additionEthyl acetate and saturated sodium bicarbonate water were added to the residue
  4. customthe organic layer was separated
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane-ethyl acetate system→ethyl acetate-2-propanol)

Sources & evidence

ORD record
ord-a3d25810f1cf4610aa25155f5dd75fe9
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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