Butanal → HCID 57245948, compound

HRID 357095Notes

Reaction equation

HRID 357095 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]([C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]3[C:23](=[O:24])[CH2:22][S:21][C:20]3=[O:25])[C:8]2=[N:7][CH:6]=1)=[O:4].[CH:28](=O)[CH2:29][CH2:30][CH3:31].N1CCCCC1>C(O)C>[CH:28](=[C:22]1[S:21][C:20](=[O:25])[N:19]([CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:13]2[C:8]3[N:9]([C:5]([C:3](=[O:4])[C:2]([F:1])([F:26])[F:27])=[CH:6][N:7]=3)[CH:10]=[CH:11][CH:12]=2)[C:23]1=[O:24])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 261ButanalHCID 8082PiperidineHCID 18936851HCID 18936851, compound

Product 1

HCID 57245948HCID 57245948, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 271 mg (0.69 mmol) of 3-[4-(3-trifluoroacetylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione and 69 μl (0.69 mmol) of n-butyraldehyde in 5 ml of ethanol, 7 μl (0.07 mmol) of piperidine was added, followed by refluxing for 1 hour. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in chloroform, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=2/1) to yield 250 mg (79.7%, light yellow oily substance) of the desired product.

Workup

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

Sources & evidence

ORD record
ord-e0137348e67c48db8315c0cea0196ce6
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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