Cesium carbonate → HCID 46831481, compound

HRID 1667743Notes

Reaction equation

HRID 1667743 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][CH2:34]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:31][CH2:30][O: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][CH2:34][CH2:33][CH2:32][N:26]5[CH2:31][CH2:30][O: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 86642833HCID 86642833, compound

Product 1

HCID 46831481HCID 46831481, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 3-morpholin-4-yl-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 20:80-100:0) to give 0.028 g of 4-(3-chloro-phenyl)-2-[6-(3-morpholin-4-yl-propoxy)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide (I.30) as a white powder. MH+/Z=498

Workup

  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 20:80-100:0)

Sources & evidence

ORD record
ord-636bb5e1d88c4e1fad51ebe6d17d9a0f
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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