N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide → 2-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide

HRID 425370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425370
C([Li])CCC.[CH3:6][N:7]([CH3:25])[S:8]([N:11]1[CH:15]=[C:14]([CH2:16][C:17]([CH3:24])([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH2:19])[N:13]=[CH:12]1)(=[O:10])=[O:9].[F:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][C:40](OC)=[O:41])=[CH:35][CH:34]=2)=[N:31][CH:32]=1>O1CCCC1>[F:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][C:40]([C:12]3[N:11]([S:8]([N:7]([CH3:6])[CH3:25])(=[O:10])=[O:9])[CH:15]=[C:14]([CH2:16][C:17]([CH3:24])([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH2:19])[N:13]=3)=[O:41])=[CH:35][CH:34]=2)=[N:31][CH:32]=1

Komponenten

5

Edukt 3

HCID 59140382N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide2×HCID 86637794Methyl [4-(5-fluoropyridin-2-yl)phenyl]acetateHCID 178418339Butyllithium

Produkt 1

HCID 667055982-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

n-Butyllithium (1.6 M in hexane) (4.19 mL, 6.7 mmol) was added to a −78° C. solution of N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide (Intermediate 4) (1.74 g, 5.59 mmol) in tetrahydrofuran (6 mL). After warming to −10° C. over 1 h, methyl [4-(5-fluoropyridin-2-yl)phenyl]acetate (1.14 g, 5.59 mmol) in tetrahydrofuran (6 mL) was added and the reaction allowed to warm to ambient temperature. After stirring at ambient temperature for 3 h, the reaction mixture was quenched with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded 2>{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide.

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with methylene chloride and ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-209afb550a8c4a50a998e2636993ce28
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106070B2

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