Propanal → 5-Propylidene-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

HRID 357186Notes

Reaction equation

HRID 357186 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[CH2:18][S:17][C:16]3=[O:21])[C:5]=12.[CH:22](=O)[CH2:23][CH3:24].N1CCCCC1>C(O)C>[CH:22](=[C:18]1[S:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:6]2[C:5]3[N:4]([CH:3]=[CH:2][N:1]=3)[CH:9]=[CH:8][CH:7]=2)[C:19]1=[O:20])[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 527PropanalHCID 8082PiperidineHCID 189368403-[4-(Imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Product 1

HCID 571127075-Propylidene-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.53 g (5.0 mmol) of 3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione and 0.36 ml (5.0 mmol) of 1-propanal in 20 ml of ethanol, 0.05 ml (0.5 mmol) of piperidine was added, followed by refluxing for 2.5 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in dichloromethane, washed with purified water and dried, after which the solvent was distilled off. The, residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=4/1). After the solvent was distilled off, the residue was recrystallized from ether to yield 1.14 g (41.7%, white crystal) of the desired product.

Workup

  1. temperatureby refluxing for 2.5 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with purified water
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe, residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=4/1)
  9. distillationAfter the solvent was distilled off
  10. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-ec5062f8936a4eb29ca13c1b232dbceb
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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