Cesium carbonate → HCID 46831478, compound

HRID 1667738Notes

Reaction equation

HRID 1667738 reaction equation
[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.[N:26]1([CH2:32][CH2:33]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.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][CH2:33][CH2:32][N:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]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

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 674454984-(3-Chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amideHCID 86642832HCID 86642832, compound

Product 1

HCID 46831478HCID 46831478, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 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), 0.060 g (0.2 mmole) of toluene-4-sulfonic acid 2-piperidin-1-yl-ethyl ester and 1 mL of dimethylformamide was added 0.160 g (0.5 mmole) of cesium carbonate. The reaction mixture 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 30:70-100:0) to give 0.027 g of 4-(3-chloro-phenyl)-2-[6-(2-piperidin-1-yl-ethoxy)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide (I.27) as a white powder. MH+/Z=482

Workup

  1. temperatureThe reaction mixture was 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 30:70-100:0)

Sources & evidence

ORD record
ord-eacb959ebdd149a0843d1db46f7f28b0
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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