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5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(E)-3-[2-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide → 2-[4-chloro-1-(3,4,5-trifluorophenyl)butyl]-5-{(E)-2-[2-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazole

HRID 546677
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 546677
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]2)[C:5]([O:14][CH3:15])=[CH:4][C:3]=1/[CH:16]=[CH:17]/[C:18]([NH:20][NH:21][C:22](=[O:37])[CH:23]([C:28]1[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=1)[CH2:24][CH2:25][CH2:26][Cl:27])=O>P(Cl)(Cl)(Cl)=O>[Cl:27][CH2:26][CH2:25][CH2:24][CH:23]([C:22]1[O:37][C:18](/[CH:17]=[CH:16]/[C:3]2[CH:4]=[C:5]([O:14][CH3:15])[C:6]([N:8]3[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]3)=[CH:7][C:2]=2[F:1])=[N:20][N:21]=1)[C:28]1[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=1
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Komponenten

3

Edukt 1

HCID 668395365-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(E)-3-[2-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide

Produkt 1

HCID 668395072-[4-chloro-1-(3,4,5-trifluorophenyl)butyl]-5-{(E)-2-[2-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazoleAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

A solution of 5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N′-{(E)-3-[2-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide (200 mg) in phosphorus oxychloride (2 mL) was stirred at 120° C. for 5.5 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 concentrated under reduced pressure to obtain 180 mg of the title compound. The property value of the compound is as follows.

Aufarbeitung

  1. waitThe reaction solution was left
  2. concentrationconcentrated under reduced pressure
  3. additionEthyl acetate and saturated sodium bicarbonate water were added to the residue
  4. customthe organic layer was separated
  5. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f146fdcefefa4e19a795fe684a22504a
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935815B2

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