Trifluoroacetic acid → HCID 19972885, Verbindung

HRID 1451929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1451929
[C:1]1([S:11]([NH:14][CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2([C:37]2[CH:38]=[CH:39][C:40]3[N:41]([CH:43]=[CH:44][N:45]=3)[CH:42]=2)[C:24]([S:27]CC2C=CC(OC)=CC=2)=[N:25][CH3:26])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:1]1([S:11]([NH:14][CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2([C:37]2[CH:38]=[CH:39][C:40]3[N:41]([CH:43]=[CH:44][N:45]=3)[CH:42]=2)[C:24](=[S:27])[NH:25][CH3:26])(=[O:12])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 10340Sodium CarbonateHCID 19972903HCID 19972903, Verbindung

Produkt 1

HCID 19972885HCID 19972885, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture comprising 0.4 g of the 2-(2-(1-naphthalenesulfonamido)ethoxy)-1-(imidazo[1,2-a]pyridin-6-yl)-1-((4-methoxybenzylthio)(methylimino)methyl)cyclohexane, 0.5 ml of anisole, 5 ml of trifluoroacetic acid and 5 ml of dichloromethane was stirred under cooling with ice for 1.5 hours, followed by the addition of ice-water. The resulting mixture was alkalinized with sodium carbonate and extracted with chloroform. The chloroform phase was dried over anhydrous magnesium sulfate and ditilled to remove the solvent. The residue was purified by silica gel column chromatography (solvent: a 80:1 dichloromethane/methanol mixture) and crystallized from ethyl acetate/n-hexane to give 0.21 g of the title compound as a white powder (yield: 65%).

Aufarbeitung

  1. temperatureunder cooling with ice for 1.5 hours
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform phase was dried over anhydrous magnesium sulfate
  4. customto remove the solvent
  5. customThe residue was purified by silica gel column chromatography (solvent
  6. customa 80:1 dichloromethane/methanol mixture) and crystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-26d493f2f24647828192745afeee143b
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05605907

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