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

HRID 1599248Notes

Reaction equation

HRID 1599248 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-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.35 9 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-c06e30cdb4b54d279245754164c7efee
Source dataset
uspto-grants-1998_04
Patent number
US05739345

Reaction notes

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