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

HRID 1667753Notes

Reaction equation

HRID 1667753 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.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:33][CH2:34][CH2:35][CH2:36][Cl:37]>CN(C)C=O>[Cl:37][CH2:36][CH2:35][CH2:34][CH2:33][O:25][C:22]1[CH:23]=[CH:24][C:19]2[N:18]=[CH:17][N:16]([C:10]3[S:11][C:12]([C:13]([NH2:15])=[O:14])=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[N:9]=3)[C:20]=2[CH:21]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 813641-Bromo-4-chlorobutaneHCID 674454984-(3-Chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide

Product 1

HCID 674446482-[6-(4-Chloro-butoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amideYield 120.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.185 g (0.5 mmole) of 4-(3-chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.25d), 1.5 mL of dimethylformamide, 0.813 g (2.5 mmole) of cesium carbonate and 0.173 mL (1.5 mmole) of 1-bromo-4-chloro-butane was heated at 100 degrees for 1 hour. The mixture was concentrated under reduced pressure, diluted with water and the resulting precipitate collected by filtration. The solid was triturated with diethyl ether to give 0.279 g of 2-[6-(4-chloro-butoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.37a) as a light brown solid.

Workup

  1. temperaturewas heated at 100 degrees for 1 hour
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additiondiluted with water
  4. filtrationthe resulting precipitate collected by filtration
  5. customThe solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-0ccc5c584b0748c793b900d043f92569
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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