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

HRID 1925548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1925548
C([O-])([O-])=O.[K+].[K+].[CH:7]12[CH2:13][CH:10]([CH2:11][CH2:12]1)[CH2:9][CH:8]2[CH2:14][NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][C:18]=1[SH:23].Br[CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1.CCCCCC.CC(=O)OCC>CN(C=O)C>[CH:10]12[CH2:13][CH:7]([CH:8]([CH2:14][NH:15][C:16]([C:17]3[C:18]([S:23][CH2:26][CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)=[N:19][CH:20]=[CH:21][CH:22]=3)=[O:24])[CH2:9]1)[CH2:12][CH2:11]2

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 147371331-(3-Bromopropyl)-4-fluorobenzeneHCID 21226206Ethyl acetate hexaneHCID 178522760N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide

Produkt 1

HCID 59487299N-(5-bicyclo-[2.2.1]heptanyl-methyl)-2-[3-(4-fluorophenyl)-propyl-sulfanyl]-pyridine-3-carboxylic acid amideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

178 mg (1.29 mmol) of K2CO3 were added to a solution of 308 mg (1.18 mmol) of N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide in DMF (5 ml), and the mixture was stirred for 60 min at RT. 255 mg (1.18 mmol) of 1-(3-bromopropyl)-4-fluorobenzene were then added and the mixture was stirred for a further 16 h at RT. Dilution with water and extraction with EA were then carried out. The organic phase was washed with water, dried over MgSO4, filtered and concentrated in vacuo. CC (hexane/EA 2:1) of the residue yielded 333 mg (0.83 mmol, 71%) of N-(5-bicyclo-[2.2.1]heptanyl-methyl)-2-[3-(4-fluorophenyl)-propyl-sulfanyl]-pyridine-3-carboxylic acid amide. MS: m/z 399.2 [M+H]+.

Aufarbeitung

  1. stirringthe mixture was stirred for a further 16 h at RT
  2. extractionDilution with water and extraction with EA
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-19dfaa88cfe14841ab9a31d7dba57701
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178684B2

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