Water → HCID 24851975, compound

HRID 599603Notes

Reaction equation

HRID 599603 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[N:21]([CH2:24][CH2:25][CH2:26]/[C:27](/[C:43]1O[C:45]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([F:55])=[CH:51][CH:50]=2)=[N:46][N:47]=1)=[CH:28]\[C:29]1[CH:34]=[CH:33][C:32]([N:35]2[CH:39]=[C:38]([CH3:40])[N:37]=[CH:36]2)=[C:31]([O:41][CH3:42])[CH:30]=1)=[N+]=[N-]>C1COCC1>[F:55][C:52]1[CH:53]=[CH:54][C:49]([CH2:48][C:45]2[N:21]3[CH2:24][CH2:25][CH2:26]/[C:27](=[CH:28]\[C:29]4[CH:34]=[CH:33][C:32]([N:35]5[CH:39]=[C:38]([CH3:40])[N:37]=[CH:36]5)=[C:31]([O:41][CH3:42])[CH:30]=4)/[C:43]3=[N:47][N:46]=2)=[CH:50][CH:51]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86615144HCID 86615144, compound

Product 1

HCID 24851975HCID 24851975, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (28 mg) and water (0.3 mL) were added to a solution of 2-{4-azido-1-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}butyl}-5-(4-fluorobenzyl)[1,3,4]oxadiazole (50 mg) in THF (5 mL), and the reaction solution was heated under reflux for four hours. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure. A solution of the residue in acetic acid (2 mL) was heated under reflux for three hours. The reaction solution was left to cool to room temperature and then 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 (carrier: Chromatorex NH; elution solvent: ethyl acetate→ethyl acetate:methanol=5:1) to obtain 40 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux for four hours
  3. waitThe reaction solution was left
  4. concentrationconcentrated under reduced pressure
  5. temperatureA solution of the residue in acetic acid (2 mL) was heated
  6. temperatureunder reflux for three hours
  7. waitThe reaction solution was left
  8. temperatureto cool to room temperature
  9. concentrationconcentrated under reduced pressure
  10. additionEthyl acetate and saturated sodium bicarbonate water were added to the residue
  11. customthe organic layer was separated
  12. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate→ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-0f90466b2b8544008688e8812a4b53b7
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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