Ammonium Acetate → HCID 178489915, compound

HRID 2235685Notes

Reaction equation

HRID 2235685 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2O[C:10](/[CH:13]=[CH:14]/[C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]4)=[C:17]([O:27][CH3:28])[CH:16]=3)=[N:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[NH4+:33]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:33][C:10](/[CH:13]=[CH:14]/[C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]4)=[C:17]([O:27][CH3:28])[CH:16]=3)=[N:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 670672252-(3-fluorophenyl)-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazole

Product 1

HCID 178489915HCID 178489915, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 2-(3-fluorophenyl)-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazole (50 mg) and ammonium acetate (205 mg) in acetic acid (3 mL) was heated under reflux at 150° C. for 1.5 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 dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1) to obtain 29 mg of the title compound. The property value of the compound is as follows.

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionEthyl acetate and saturated sodium bicarbonate water were added to the residue
  5. customthe organic layer was separated
  6. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-e4e2f7c98cda41ae929932c032547ca9
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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