Ethanamine, 2,2,2-trifluoro- → (E)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methyl-N-(2,2,2-trifluoroethyl)benzamide

HRID 587199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587199
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:22]([F:25])([F:24])[F:23])/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[C:14]([CH3:21])[CH:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:26][C:27]([F:31])([F:30])[CH2:28][NH2:29].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:8][C:6]1[CH:5]=[C:4]([CH:9]([C:22]([F:25])([F:24])[F:23])/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:29][CH2:28][C:27]([F:31])([F:30])[F:26])=[O:18])=[C:14]([CH3:21])[CH:13]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Komponenten

8

Edukt 5

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86675124(E)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoic acid

Produkt 1

HCID 86675125(E)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methyl-N-(2,2,2-trifluoroethyl)benzamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of (E)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoic acid in DMF was added 2,2,2-trifluoroethylamine, HOBt.H2O, EDC.HCl and DIPEA, and the reaction mixture was stirred at 25° C. for 18 h. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with hexane:EtOAc afforded a white semi-solid (110 mg, 50%): 1H NMR (400 MHz, CDCl3) 7.40 (m, 2H), 7.26 (m, 3H), 6.56 (d, J=16.0 Hz, 1H), 6.48 (dd, J=16.0, 8.0 Hz, 1H), 5.82 (br s, 1H), 4.08 (m, 3H), 2.52 (s, 3H); ESIMS m/z 468.40 ([M−H]−); IR (thin film) 1657, 1113, 804 cm−1.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (SiO2, 100-200 mesh
  6. washeluting with hexane

Quellen und Nachweise

ORD-Eintrag
ord-c49ec889ae1544d1a27b93626a80702d
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226500B2

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