(Trifluoromethyl)trimethylsilane → HCID 57377969, Verbindung

HRID 76014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 76014
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[N:21]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[N:22]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:30]([Si](C)(C)C)([F:33])([F:32])[F:31].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCOC(C)=O>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([C:1]([OH:3])([CH3:2])[C:30]([F:33])([F:32])[F:31])=[CH:9][CH:8]=2)(=[O:12])=[O:11])=[C:15]([N:21]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[N:22]2)[CH:16]=1

Komponenten

5

Edukt 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 573784044-acetyl-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)benzenesulfonamide

Produkt 1

HCID 57377969HCID 57377969, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 4-acetyl-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)-benzene-sulfonamide (synthesized according to general procedures F and G, 500 mg, 1.17 mmol) was added CF3-TMS (trifluoromethyl-trimethylsilane) (4.7 mL, 0.5 M solution in THF), followed by TBAF (tetra-n-butylammonium fluoride)(2.34 mL, 1.0 M solution in THF) at 0° C., and the solution was stirred at room temperature for 16 hours. Both TLC and LCMS analysis indicated ˜10-15% completion of reaction. The reaction mixture was diluted with EtOAc (50 mL) and the organics were washed with washed with 2 N HCl (2×25 mL), water (25 mL), and brine (25 mL). The organics were subsequently dried (Na2SO4), concentrated in vacuo, and purified by automated flash chromatography followed by preparative HPLC to afford the title compound as a white powder: MS (ES) M+H expected 498.1, found 498.0.

Aufarbeitung

  1. custom˜10-15% completion of reaction
  2. washthe organics were washed
  3. washwith washed with 2 N HCl (2×25 mL), water (25 mL), and brine (25 mL)
  4. dry with materialThe organics were subsequently dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by automated flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-63196df21b2f4081bc478afeefdf76f5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835468B2

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