Water → 3-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-trifluoroethyl-phenyl}-5-methyl-[1,2,4]oxadiazole

HRID 471376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471376
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([NH:20][OH:21])=[NH:19])=[C:16]([CH3:24])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:29][C:30]([F:36])([F:35])CC(Cl)=O.O.[CH3:38][CH2:39]OC(C)=O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:26])([F:28])[F:27])[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]4[N:19]=[C:38]([CH3:39])[O:21][N:20]=4)=[C:16]([CH2:24][C:30]([F:36])([F:35])[F:29])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 27833433,3,3-Trifluoropropionyl chlorideHCID 178423542HCID 178423542, Verbindung

Produkt 1

HCID 866585243-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-trifluoroethyl-phenyl}-5-methyl-[1,2,4]oxadiazoleAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-hydroxy-2-methyl-benzamidine (i.e product of Step 1, Example 8, 400 mg, 0.93 mmol) in pyridine (10 mL) was added 3,3,3-trifluoropropionic acid chloride (0.271 g, 1.85 mmol) via syringe and the mixture was stirred at reflux for 30 min and at 140° C. in a microwave oven for 1 h. Water and EtOAc were added after cooling and the aqueous layer was extracted with EtOAc. Combined organic layers were dried (Na2SO4) and concentrated in vacuum. The residue was purified by flash chromatography on silica gel and yielded the title compound (260 mg, 53%).

Aufarbeitung

  1. temperatureafter cooling
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialCombined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9e65182763f4472a9f5ed2838566f012
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633134B2

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