Dimethylamine → HCID 46831480, compound

HRID 1667741Notes

Reaction equation

HRID 1667741 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[CH:11][N:10]([C:13]3[S:14][C:15]([C:25]([NH2:27])=[O:26])=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=4)[N:17]=3)[C:9]=2[CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:35][NH:36][CH3:37]>[I-].[K+].CN(C)C=O>[Cl:24][C:20]1[CH:19]=[C:18]([C:16]2[N:17]=[C:13]([N:10]3[C:9]4[CH:28]=[C:5]([O:4][CH2:3][CH2:2][N:36]([CH3:37])[CH3:35])[CH:6]=[CH:7][C:8]=4[N:12]=[CH:11]3)[S:14][C:15]=2[C:25]([NH2:27])=[O:26])[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 67443711HCID 67443711, compound

Product 1

HCID 46831480HCID 46831480, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.043 g (0.1 mmole) of 2-[6-(2-chloro-ethoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.28a), 1 mL of dimethylformamide, 0.069 g (0.5 mmole) of potassium carbonate, 0.001 g of potassium iodide and 0.150 mL (0.3 mmole) of dimethylamine was stirred at 100 degrees for 6 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 0.034 g of 4-(3-chloro-phenyl)-2-[6-(2-dimethylamino-ethoxy)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide (I.29) as a white powder. MH+/Z=442

Workup

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

Sources & evidence

ORD record
ord-cb28e25c14454893b91a6831f4ed9944
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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