Butanal → HCID 57103741, compound

HRID 357097Notes

Reaction equation

HRID 357097 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]([C:5]1[N:9]2[C:10]([S: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])=[CH:11][CH:12]=[CH:13][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][S:14][C:10]2[N:9]3[C:5]([C:3](=[O:4])[C:2]([F:26])([F:1])[F:27])=[CH:6][N:7]=[C:8]3[CH:13]=[CH:12][CH:11]=2)[C:23]1=[O:24])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 261ButanalHCID 8082PiperidineHCID 18936734HCID 18936734, compound

Product 1

HCID 57103741HCID 57103741, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 250 mg (0.6 mmol) of 3-[4-(3-trifluoroacetylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione and 54 μl (0.6 mmol) of n-butyraldehyde in 5 ml of ethanol, 6 μl (0.06 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 saturated aqueous sodium hydrogen carbonate 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 200 mg (70.0%, 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 saturated aqueous sodium hydrogen carbonate
  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-2248eb88589344208d51e3e0b003340a
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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