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Thiazolidinedione → 5-{4-(3-Methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzylidene}thiazolidine-2,4-dione

HRID 1953667
Notes
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Reaction equation

HRID 1953667 reaction equation
[CH:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C:9]2[N:10]([CH3:18])[C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:5][CH:4]=1)=O.[S:21]1[CH2:25][C:24](=[O:26])[NH:23][C:22]1=[O:27].N1CCCCC1>C(O)C>[CH3:18][N:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[N:17]=[C:9]1[CH2:8][O:7][C:6]1[CH:19]=[CH:20][C:3]([CH:1]=[C:25]2[S:21][C:22](=[O:27])[NH:23][C:24]2=[O:26])=[CH:4][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 23298364Benzaldehyde,4-[(3-methyl-3h-imidazo[4,5-b]pyridin-2-yl)methoxy]-

Product 1

HCID 543676935-{4-(3-Methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzylidene}thiazolidine-2,4-dioneYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.35 g of 2-(4-formylphenoxymethyl)-3-methylimidazo [5,4-b]pyridine (prepared as described in Preparation 112), 0.31 g of 2,4-thiazolidinedione, 0.26 ml of piperidine and 10 ml of ethanol was heated under reflux for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure and the residue was crystallized by trituration with water. The crystals were collected by filtration and washed with water and then with ethyl acetate, to give 0.38 g of the title compound, melting at 279-281° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. customthe residue was crystallized by trituration with water
  5. filtrationThe crystals were collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-6f6df774b5454bae9da40052934a3dab
Source dataset
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06117893

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes