Cesium carbonate → 4-(3-Chloro-phenyl)-2-(6-cyclohexyloxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide

HRID 1667734Notes

Reaction equation

HRID 1667734 reaction equation
[CH:1]1(OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[N:26]=[C:27]([N:33]3[C:37]4[CH:38]=[C:39]([OH:42])[CH:40]=[CH:41][C:36]=4[N:35]=[CH:34]3)[S:28][C:29]=2[C:30]([NH2:32])=[O:31])[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[N:26]=[C:27]([N:33]3[C:37]4[CH:38]=[C:39]([O:42][CH:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[CH:40]=[CH:41][C:36]=4[N:35]=[CH:34]3)[S:28][C:29]=2[C:30]([NH2:32])=[O:31])[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 13722Cyclohexyl p-toluenesulfonateHCID 674454984-(3-Chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide

Product 1

HCID 468311764-(3-Chloro-phenyl)-2-(6-cyclohexyloxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amideYield 59.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.051 g (0.2 mmole) of toluene-4-sulfonic acid cyclohexyl ester, 0.037 g (0.1 mmole) of 4-(3-chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.25d) and 1 mL of dimethylformamide was added 0.163 g (0.5 mmole) of cesium carbonate. The mixture 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 40:60-100:0) to give 0.027 g of 4-(3-chloro-phenyl)-2-(6-cyclohexyloxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.25) as a white powder. MH+/Z=453

Workup

  1. temperatureThe mixture was 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 40:60-100:0)

Sources & evidence

ORD record
ord-97ce17d18f6549c186ee47e4c1b084fd
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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