Dimethyl Sulfoxide → HCID 66906160, Verbindung

HRID 1691767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691767
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1F)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[C:22]([O:26][C:27](=[O:54])[N:28]([C@@H:42]([C:44]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:47]=[CH:46][CH:45]=1)[CH3:43])[CH2:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH:31]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([CH3:25])([CH3:24])[CH3:23]>C1COCC1.O>[C:5]([C:4]1[CH:7]=[C:8]([F:11])[C:9]([N:33]2[CH2:34][CH2:35][CH:30]([CH2:29][N:28]([C@@H:42]([C:44]3[C:53]4[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=4)[CH:47]=[CH:46][CH:45]=3)[CH3:43])[C:27](=[O:54])[O:26][C:22]([CH3:23])([CH3:24])[CH3:25])[CH:31]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:32]2)=[C:2]([F:1])[CH:3]=1)#[N:6]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 5938143,4,5-TrifluorobenzonitrileHCID 59178521HCID 59178521, Verbindung

Produkt 1

HCID 66906160HCID 66906160, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 96 mg of 3,4,5-trifluorobenzonitrile, 113 mg of potassium carbonate, and 3.0 mL of DMSO was added a solution of 181 mg of a crude product of tert-butyl[(1R)-1-(1-naphthyl)ethyl][(3-phenylpiperidin-4-yl)methyl]carbamate in 3.0 mL of THF, the reaction vessel was tightly sealed, and the mixture was heated at 100° C. overnight. The reaction mixture was cooled to room temperature, and water was then added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 232 mg of tert-butyl {[1-(4-cyano-2,6-difluorophenyl)-3-phenylpiperidin-4-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate as a crude product. FAB+: 582

Aufarbeitung

  1. customthe reaction vessel was tightly sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-16cc81cbf1e44b348cf24eb976af3907
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153658B2

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