Chloroacetaldehyde → 3-[3-(Imidazo[1,2-a]pyridin-8-yloxy)propyl]thiazolidine-2,4-dione

HRID 357146Notes

Reaction equation

HRID 357146 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[C:16](=[O:17])[CH2:15][S:14][C:13]2=[O:18])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH2:20][CH:21]=O>C(O)C>[N:1]1[CH:20]=[CH:21][N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]3[C:16](=[O:17])[CH2:15][S:14][C:13]3=[O:18])[C:2]=12

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 189367993-[3-(2-Aminopyridin-3-yloxy)propyl]thiazolidine-2,4-dione

Product 1

HCID 189368873-[3-(Imidazo[1,2-a]pyridin-8-yloxy)propyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.01 g (15 mmol) of 3-[3-(2-aminopyridin-3-yloxy)propyl]thiazolidine-2,4-dione in 40 ml of ethanol, 15 ml of a 40% chloroacetaldehyde solution was added at 60° C., followed by refluxing for 2 hours. 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=1/4) to yield 2.92 g (66.8%, white powder) of the desired product.

Workup

  1. temperatureby refluxing for 2 hours
  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=1/4)

Sources & evidence

ORD record
ord-6dac5db317f44300943a00366d75e4de
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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