Ammonium Acetate → HCID 178489930, compound

HRID 546727Notes

Reaction equation

HRID 546727 reaction equation
C([O-])(=O)C.[NH4+:5].[F:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2O[C:16](/[CH:19]=[CH:20]/[C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]4)=[C:23]([O:33][CH3:34])[CH:22]=3)=[N:17][N:18]=2)=[CH:9][CH:8]=1>C(O)(=O)C>[F:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[NH:5][C:16](/[CH:19]=[CH:20]/[C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]4)=[C:23]([O:33][CH3:34])[CH:22]=3)=[N:17][N:18]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 66839447(4-fluorophenyl)-{5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazol-2-yl}amine

Product 1

HCID 178489930HCID 178489930, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

Acetic acid (10 mL) and ammonium acetate (6.8 g) were added to (4-fluorophenyl)-{5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazol-2-yl}amine (692 mg), and the reaction solution was stirred at 150° C. for 12 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 insoluble matter generated during separation was added to the resulting extract, and THF and ethanol were further added to provide a mixed solution. The mixed solution was concentrated under reduced pressure and solidified with ethyl acetate and diethyl ether to obtain 372 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. customThe insoluble matter generated during separation
  7. additionwas added to the resulting
  8. extractionextract
  9. additionTHF and ethanol were further added
  10. customto provide a mixed solution
  11. concentrationThe mixed solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6db9609c26ce4b25a5fa616b7320bdce
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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