Dimethylformamide → 4-(3-Chloro-phenyl)-2-{6-[2-hydroxy-3-(4-methyl-piperazin-1-yl)-propoxy]-benzoimidazol-1-yl}-thiazole-5-carboxylic acid amide

HRID 1667758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667758
[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][CH2:26][CH:27]5[CH2:29][O:28]5)[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.C(=O)([O-])[O-].[K+].[K+].[NH:36]1[CH2:41][CH2:40]O[CH2:38][CH2:37]1.[CH3:42][N:43](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][CH2:26][CH:27]([OH:28])[CH2:29][N:36]5[CH2:41][CH2:40][N:43]([CH3:42])[CH2:38][CH2:37]5)[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 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 866428344-(3-Chloro-phenyl)-2-(6-oxiranylmethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide

Produkt 1

HCID 468323044-(3-Chloro-phenyl)-2-{6-[2-hydroxy-3-(4-methyl-piperazin-1-yl)-propoxy]-benzoimidazol-1-yl}-thiazole-5-carboxylic acid amide

Versuchsvorschrift

A mixture of 0.021 g (0.05 mmole) of 4-(3-chloro-phenyl)-2-(6-oxiranylmethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.39a), 0.5 mL of dimethylformamide, 0.035 g (0.25 mmole) of potassium carbonate and 0.009 mL (0.1 mmole) of morpholine was heated at 100 degrees for 3 hours. 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 20:80-100:0) to give 0.012 g of 4-(3-chloro-phenyl)-2-{6-[2-hydroxy-3-(4-methyl-piperazin-1-yl)-propoxy]-benzoimidazol-1-yl}-thiazole-5-carboxylic acid amide (I.40) as a white powder. MH+/Z=514

Aufarbeitung

  1. temperaturewas heated at 100 degrees for 3 hours
  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 20:80-100:0)

Quellen und Nachweise

ORD-Eintrag
ord-08b1d3d4c5244cdabc16e8643091fcd1
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

Notizen zur Reaktion

Wird geladen…