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

HRID 356262Notes

Reaction equation

HRID 356262 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

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-6ef61111848d47949b31df0edb070d1e
Source dataset
uspto-grants-1998_11
Patent number
US05834501

Reaction notes

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