HOAt → (E)-2-Chloro-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-N-(1-(2,2,2-trifluoroethylcarbamoyl)cyclopropyl)benzamide

HRID 1503784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503784
[Cl:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[CH:13]([C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=2)[C:14]([F:17])([F:16])[F:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:27][C:28]1([C:31]([NH:33][CH2:34][C:35]([F:38])([F:37])[F:36])=[O:32])[CH2:30][CH2:29]1.F[P-](F)(F)(F)(F)F.ClC1N(C)CC[NH+]1C.ON1C2N=CC=CC=2N=N1>C(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[CH:13]([C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=2)[C:14]([F:16])([F:15])[F:17])[CH:8]=[CH:7][C:3]=1[C:4]([NH:27][C:28]1([C:31](=[O:32])[NH:33][CH2:34][C:35]([F:37])([F:38])[F:36])[CH2:30][CH2:29]1)=[O:6]

Komponenten

7

Edukt 4

HCID 181649HOAtHCID 218684192-Chloro-1,3-dimethylimidazolidin-1-ium;hexafluorophosphateHCID 654644011-amino-N-(2,2,2-trifluoroethyl)cyclopropanecarboxamideHCID 86722568(E)-2-chloro-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzoic acid

Produkt 1

HCID 86722567(E)-2-Chloro-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-N-(1-(2,2,2-trifluoroethylcarbamoyl)cyclopropyl)benzamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of (E)-2-chloro-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzoic acid (300 mg, 0.67 mmol) and 1-amino-N-(2,2,2-trifluoroethyl)cyclopropanecarboxamide (148 mg, 0.81 mmol) in DCM/DMF (5 mL, 1:1), 2-chloro-1,3-dimethylimidazolidinium hexafluorophosphate (CIP) (92 mg, 0.33 mmol), 1-hydroxy-7-azabenzotriazole (HOAt) (48 mg, 0.33 mmol) and DMAP (5 mol %) were added, and the resulting mixture was stirred at room temperature (RT) for 4 h. The reaction mixture was poured into ice-water and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered, concentrated and the residue was purified by column chromatography on silica (100-200 mesh) eluting with 30% EtOAc in petroleum ether to give the title compound as pale yellow gum (300 mg, 75%). Characterization data for this molecule is listed in Table 2.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography on silica (100-200 mesh)
  6. washeluting with 30% EtOAc in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-1d76034e53a8425d884b4ca8f3e8a555
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212164B2

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