Potassium Iodide → HCID 46832589, compound

HRID 1667754Notes

Reaction equation

HRID 1667754 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[CH:13][N:12]([C:15]3[S:16][C:17]([C:27]([NH2:29])=[O:28])=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=4)[N:19]=3)[C:11]=2[CH:30]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>CN(C)C=O>[Cl:26][C:22]1[CH:21]=[C:20]([C:18]2[N:19]=[C:15]([N:12]3[C:11]4[CH:30]=[C:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:43]5[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]5)[CH:8]=[CH:9][C:10]=4[N:14]=[CH:13]3)[S:16][C:17]=2[C:27]([NH2:29])=[O:28])[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 674446482-[6-(4-Chloro-butoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide

Product 1

HCID 46832589HCID 46832589, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.023 g (0.05 mmole) of 2-[6-(4-chloro-butoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.37a), 0.5 mL of dimethylformamide, 0.035 g (0.25 mmole) of potassium carbonate, 0.001 g of potassium iodide and 0.017 mL (0.15 mmole) of 1-methyl-piperazine was stirred at 100 degrees for 3 hours. The mixture was concentrated under reduced pressure, and diluted with 20 mL of water. The precipitate was collected by filtration and the solid triturated with diethyl ether to give 0.018 g of 4-(3-chloro-phenyl)-2-{6-[4-(4-methyl-piperazin-1-yl)-butoxy]-benzoimidazol-1-yl}-thiazole-5-carboxylic acid amide (I.37) as a white powder. MH+/Z=525

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with 20 mL of water
  3. filtrationThe precipitate was collected by filtration
  4. customthe solid triturated with diethyl ether

Sources & evidence

ORD record
ord-1f6bacabf773477c88a3ca83000a0617
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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