Diisopropylethylamine → 2-[4-chloro-1-(4-chlorophenyl)butyl]-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}[1,3,4]oxadiazole

HRID 599656Notes

Reaction equation

HRID 599656 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][CH2:11][CH2:12][CH2:13][CH:14]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[C:15]([OH:17])=O.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.Cl.Cl.[CH3:42][O:43][C:44]1[CH:45]=[C:46](/[CH:56]=[CH:57]/[C:58]([NH:60][NH2:61])=O)[CH:47]=[CH:48][C:49]=1[N:50]1[CH:54]=[C:53]([CH3:55])[N:52]=[CH:51]1>C(Cl)Cl.O>[Cl:10][CH2:11][CH2:12][CH2:13][CH:14]([C:15]1[O:17][C:58](/[CH:57]=[CH:56]/[C:46]2[CH:47]=[CH:48][C:49]([N:50]3[CH:54]=[C:53]([CH3:55])[N:52]=[CH:51]3)=[C:44]([O:43][CH3:42])[CH:45]=2)=[N:60][N:61]=1)[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 66839298(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid hydrazide dihydrochlorideHCID 670673305-Chloro-2-(4-chlorophenyl)pentanoic acid

Product 1

HCID 670673572-[4-chloro-1-(4-chlorophenyl)butyl]-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}[1,3,4]oxadiazoleYield 52.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

IPEA (2.5 mL), 5-chloro-2-(4-chlorophenyl)pentanoic acid (430 mg) and BOPCl (0.44 g) were added to a suspension of (E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid hydrazide dihydrochloride (500 mg) in methylene chloride (15 mL) at room temperature, and the reaction solution was stirred at room temperature for 14 hours. Water was added to the reaction solution, followed by extraction with chloroform. The resulting extract was washed with a saturated sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure. A solution of the residue in phosphorus oxychloride (4 mL) was heated under reflux for five hours. The reaction solution was left to cool to room temperature and 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) to obtain 366 mg of the title compound. The property value of the compound is as follows.

Workup

  1. extractionfollowed by extraction with chloroform
  2. extractionThe resulting extract
  3. washwas washed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. temperatureA solution of the residue in phosphorus oxychloride (4 mL) was heated
  7. temperatureunder reflux for five 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 resulting residue
  12. extractionfollowed by extraction with chloroform
  13. extractionThe resulting extract
  14. dry with materialwas dried over magnesium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-4a807abf44c847f6bf59e74de514f15c
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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