Ammonium Acetate → 8-(4-fluorophenyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrimidin-7-one

HRID 546729Notes

Reaction equation

HRID 546729 reaction equation
C([O-])(=O)C.[NH4+:5].[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([C:18]2O[C:20](/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]4)=[C:27]([O:37][CH3:38])[CH:26]=3)=[N:21][N:22]=2)[C:14](=[O:17])[CH:15]=[CH2:16])=[CH:9][CH:8]=1>C(O)(=O)C>[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:14](=[O:17])[CH2:15][CH2:16][N:5]3[C:20](/[CH:23]=[CH:24]/[C:25]4[CH:30]=[CH:29][C:28]([N:31]5[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]5)=[C:27]([O:37][CH3:38])[CH:26]=4)=[N:21][N:22]=[C:18]23)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 66839215N-(4-fluorophenyl)-N-{5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazol-2-yl}acrylamide

Product 1

HCID 576092658-(4-fluorophenyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrimidin-7-oneYield 4.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

Acetic acid (1 mL) and ammonium acetate (0.11 g) were added to N-(4-fluorophenyl)-N-{5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazol-2-yl}acrylamide (22 mg), and the reaction solution was stirred at 150° C. for six hours. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure. A saturated sodium bicarbonate solution was added to the resulting residue, followed by extraction with chloroform. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system, then ethyl acetate-methanol system) to obtain 1 mg of the title compound. The property values of the compound are as follows.

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionA saturated sodium bicarbonate solution was added to the resulting residue
  5. extractionfollowed by extraction with chloroform
  6. extractionThe resulting extract
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (carrier
  10. washelution solvent

Sources & evidence

ORD record
ord-23944a3d321a497092f23aba55caf695
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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