Cesium carbonate → HCID 46831482, Verbindung

HRID 1667745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667745
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:16]3[C:20]4[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1.[CH3:26][N:27]([CH3:42])[CH2:28][CH2:29][CH2:30]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:16]3[C:20]4[CH:21]=[C:22]([O:25][CH2:30][CH2:29][CH2:28][N:27]([CH3:42])[CH3:26])[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 214550723-(Dimethylamino)propyl 4-methylbenzene-1-sulfonateHCID 674454984-(3-Chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide

Produkt 1

HCID 46831482HCID 46831482, VerbindungAusbeute 39,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.037 g (0.1 mmole) of 4-(3-chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.25d), 0.051 g (0.2 mmole) of toluene-4-sulfonic acid 3-dimethylamino-propyl ester, 1 mL of dimethylformamide and 0.160 g (0.5 mmole) of cesium carbonate was heated at 100 degrees for 30 minutes. The mixture was cooled, the solid was removed by filtration and the filtrate purified by reverse phase silica gel chromatography, eluting with acetonitrile-water (gradient 30:70-100:0) to give 0.018 g of 4-(3-chloro-phenyl)-2-[6-(3-dimethylamino-propoxy)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide (I.31) as a white powder. MH+/Z=456

Aufarbeitung

  1. temperaturewas heated at 100 degrees for 30 minutes
  2. temperatureThe mixture was cooled
  3. customthe solid was removed by filtration
  4. customthe filtrate purified by reverse phase silica gel chromatography
  5. washeluting with acetonitrile-water (gradient 30:70-100:0)

Quellen und Nachweise

ORD-Eintrag
ord-dc8ae7b469ba4f20a566f79e259a9fca
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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