Diisopropylethylamine → (E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)-2-(trifluoromethoxy)benzamide

HRID 587216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587216
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:27]([F:30])([F:29])[F:28])/[CH:11]=[CH:12]/[C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[C:15]([O:22][C:23]([F:26])([F:25])[F:24])[CH:14]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[NH2:31][CH2:32][C:33]([NH:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[O:34].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:27]([F:30])([F:29])[F:28])/[CH:11]=[CH:12]/[C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:31][CH2:32][C:33](=[O:34])[NH:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[O:18])=[C:15]([O:22][C:23]([F:24])([F:25])[F:26])[CH:14]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 247051432-Amino-N-(2,2,2-trifluoroethyl)acetamideHCID 86675151(E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-(trifluoromethoxy)benzoic acid

Produkt 1

HCID 86675150(E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)-2-(trifluoromethoxy)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-(trifluoromethoxy)benzoic acid (0.25 g, 0.52 mmol), 2-amino-N-(2,2,2-trifluoroethyl)acetamide (0.158 g, 0.62 mmol), PyBOP (0.40 g, 0.78 mmol) and DIPEA (0.134 g, 1.04 mmol) in CH2Cl2 (10.0 mL) were stirred at ambient temperature for 16 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined CH2Cl2 layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with 20% EtOAc/pet ether) afforded the title compound as a pale yellow gummy material (0.15 g, 47%).

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. washThe combined CH2Cl2 layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification
  6. washby flash column chromatography (SiO2, 100-200 mesh; eluting with 20% EtOAc/pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-4bb4ebe531f940da8ae0550760d89953
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226500B2

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