Dimethyl Sulfoxide → HCID 66906160, compound

HRID 1691767Notes

Reaction equation

HRID 1691767 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 66906160HCID 66906160, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-16cc81cbf1e44b348cf24eb976af3907
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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