Water → (4-fluorophenyl)-{5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazol-2-yl}amine

HRID 546726Notes

Reaction equation

HRID 546726 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:17]=[CH:18]/[C:19]([NH:21][NH2:22])=[O:20])[CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=O)=[CH:26][CH:25]=1.O>CN(C=O)C>[F:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]2[O:20][C:19](/[CH:18]=[CH:17]/[C:7]3[CH:8]=[CH:9][C:10]([N:11]4[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]4)=[C:5]([O:4][CH3:3])[CH:6]=3)=[N:21][N:22]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 709554-Fluorophenyl isocyanateHCID 66839298(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid hydrazide dihydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TEA (1.25 mL) was added to a solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid hydrazide dihydrochloride (771 mg) in DMF (15 mL) at room temperature, and the reaction solution was stirred at room temperature for 10 minutes. 4-Fluorophenyl isocyanate (0.26 mL) was added to the reaction solution at room temperature, and the reaction solution was stirred at room temperature for one hour. The reaction solution was added to cold water. The generated solid was separated by filtration, washed with water and diethyl ether and then dried at 60° C. for three hours. Phosphorus oxychloride (15 mL) was added to the resulting solid at room temperature, and the reaction solution was heated under reflux for three 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 residue. The generated solid was separated by filtration, washed with diethyl ether and then dried at 60° C. for one hour to obtain 820 mg of the title compound. The property value of the compound is as follows.

Workup

  1. stirringthe reaction solution was stirred at room temperature for one hour
  2. customThe generated solid was separated by filtration
  3. washwashed with water and diethyl ether
  4. customdried at 60° C. for three hours
  5. additionPhosphorus oxychloride (15 mL) was added to the resulting solid at room temperature
  6. temperaturethe reaction solution was heated
  7. temperatureunder reflux for three hours
  8. waitThe reaction solution was left
  9. temperatureto cool to room temperature
  10. concentrationconcentrated under reduced pressure
  11. additionA saturated sodium bicarbonate solution was added to the residue
  12. customThe generated solid was separated by filtration
  13. washwashed with diethyl ether
  14. customdried at 60° C. for one hour

Sources & evidence

ORD record
ord-67f13827c9904387b7823087d9cfd07f
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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