Potassium Carbonate → N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[[3,3-difluoro-3-(4-fluoro-phenyl)-propyl]sulfanyl]-pyridine-3-carboxylic acid amide

HRID 2044171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2044171
C([O-])([O-])=O.[K+].[K+].CS(O[CH2:12][CH2:13][C:14]([F:23])([F:22])[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)(=O)=O.[CH:24]12[CH2:30][CH:27]([CH2:28][CH2:29]1)[CH2:26][CH:25]2[CH2:31][NH:32][C:33](=[O:41])[C:34]1[CH:39]=[CH:38][CH:37]=[N:36][C:35]=1[SH:40].CCCCCC.CC(=O)OCC>CN(C=O)C>[CH:27]12[CH2:30][CH:24]([CH:25]([CH2:31][NH:32][C:33]([C:34]3[C:35]([S:40][CH2:12][CH2:13][C:14]([F:22])([F:23])[C:15]4[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=4)=[N:36][CH:37]=[CH:38][CH:39]=3)=[O:41])[CH2:26]1)[CH2:29][CH2:28]2

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 866453903,3-Difluoro-3-(4-fluorophenyl)-propyl methanesulfonateHCID 178522760N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide

Produkt 1

HCID 59487304N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[[3,3-difluoro-3-(4-fluoro-phenyl)-propyl]sulfanyl]-pyridine-3-carboxylic acid amideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

553 mg (4 mmol) of K2CO3 and 268 mg (1.0 mmol) of 3,3-difluoro-3-(4-fluorophenyl)-propyl methanesulfonate were added in succession to a solution of 262 mg (1.0 mmol) of N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide in DMF (3 ml), and the mixture was heated for 3 h at 60° C. Dilution with water and extraction with EA were then carried out. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 7:3) of the residue yielded 229 mg (0.5 mmol, 53%) of N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[[3,3-difluoro-3-(4-fluoro-phenyl)-propyl]sulfanyl]-pyridine-3-carboxylic acid amide. MS: m/z 435.2 [M+H]+.

Aufarbeitung

  1. extractionDilution with water and extraction with EA
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-aa9d633aa08848d6ad39a8f2ee64db82
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586755B2

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