(Trifluoromethyl)trimethylsilane → HCID 57377969, Verbindung

HRID 218212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 218212
[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-e84ea3eb6e3f4e04b2319103f4348481
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198309B2

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