Ammonium Acetate → HCID 24852454, compound

HRID 1009350Notes

Reaction equation

HRID 1009350 reaction equation
Cl[CH2:2][CH2:3][CH2:4]/[C:5](/[C:21]1O[C:23]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[N:24][N:25]=1)=[CH:6]\[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]2)=[C:9]([O:19][CH3:20])[CH:8]=1.C([O-])(=O)C.[NH4+:37]>C(O)(=O)C>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]2[N:37]=[C:21]3/[C:5](=[CH:6]/[C:7]4[CH:12]=[CH:11][C:10]([N:13]5[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]5)=[C:9]([O:19][CH3:20])[CH:8]=4)/[CH2:4][CH2:3][CH2:2][N:25]3[N:24]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 670672392-{4-chloro-1-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}butyl}-5-(4-fluorophenyl)[1,3,4]oxadiazole

Product 1

HCID 24852454HCID 24852454, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-{4-chloro-1-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}butyl}-5-(4-fluorophenyl)-[1,3,4]oxadiazole (85 mg) and ammonium acetate (290 mg) in acetic acid (3 mL) was heated under reflux for 10 hours. The reaction solution was left to cool to room temperature and concentrated under reduced pressure. Methylene chloride and a 1 N sodium hydroxide solution were added to the residue, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 34 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperatureunder reflux for 10 hours
  2. waitThe reaction solution was left
  3. concentrationconcentrated under reduced pressure
  4. additionMethylene chloride and a 1 N sodium hydroxide solution were added to the residue
  5. customthe organic layer was separated
  6. washThe resulting organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane:ethyl acetate=1:1->ethyl acetate)

Sources & evidence

ORD record
ord-c704900b60fb442f92669db5c599af9c
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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