Dimethylformamide → HCID 67443711, compound

HRID 1667739Notes

Reaction equation

HRID 1667739 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+].CN(C)C=O.Br[CH2:38][CH2:39][Cl:40]>O>[Cl:40][CH2:39][CH2:38][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

6

Reactant 4

HCID 6228DimethylformamideHCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 674454984-(3-Chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide

Product 1

HCID 67443711HCID 67443711, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.371 g (1 mmole) of 4-(3-chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.25d), 1.63 g (5 mmole) of cesium carbonate and 3 mL of dimethylformamide was added 0.249 mL (3 mmole) of 1-bromo-2-chloro-ethane. The mixture was heated at 100 degrees for 30 minutes. The cooled mixture was diluted with 20 mL of water and the resulting precipitate collected by filtration and then air dried. The solid was triturated with acetonitrile to give 0.269 g of 2-[6-(2-chloro-ethoxy)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.28a) as a yellow solid.

Workup

  1. temperatureThe mixture was heated at 100 degrees for 30 minutes
  2. filtrationthe resulting precipitate collected by filtration
  3. customair dried
  4. customThe solid was triturated with acetonitrile

Sources & evidence

ORD record
ord-ce2baa5ffbc143b0b5bc79ae2910fbfe
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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