Thiazolidinedione → HCID 73885113, compound

HRID 1699927Notes

Reaction equation

HRID 1699927 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18].[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31].N1CCCCC1>C(O)C>[Cl:1][C:2]1[CH:22]=[C:21]([CH:23]=[C:29]2[S:25][C:26](=[O:31])[NH:27][C:28]2=[O:30])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 22388400HCID 22388400, compound

Product 1

HCID 73885113HCID 73885113, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of methyl 3-(2-chloro-4-formylbenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (200 mg, 0.582 mmol), thiazolidine-2,4-dione (82 mg, 0.698 mmol) and piperidine (25 mg, 0.291 mmol) in ethanol (4 ml) was refluxed under heating overnight. The reaction mixture was cooled, and the precipitated crystals were filtrated to give the objective compound (189 mg) as pale-yellow crystals.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating overnight
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe precipitated crystals were filtrated

Sources & evidence

ORD record
ord-773bfab22e834ceb8323b3f515337c43
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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