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 1925551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1925551
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-69db6f86b5ff4458878ad3b3bca085b0
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178684B2

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