Thiazolidinedione → 3-(Imidazo[1,2-a]pyridin-5-yl)methylthiazolidine-2,4-dione

HRID 357058Notes

Reaction equation

HRID 357058 reaction equation
O[CH2:2][C:3]1[N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[S:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1=[O:22].C1CCN2C(=NCCC2)CC1>ClCCl.CN(C)C=O.O>[N:11]1[CH:10]=[CH:9][N:8]2[C:3]([CH2:2][N:18]3[C:19](=[O:21])[CH2:20][S:16][C:17]3=[O:22])=[CH:4][CH:5]=[CH:6][C:7]=12

Participants

8

Reactant 4

HCID 5437ThiazolidinedioneHCID 24386Thionyl ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11126423{Imidazo[1,2-a]pyridin-5-yl}methanol

Product 1

HCID 189368603-(Imidazo[1,2-a]pyridin-5-yl)methylthiazolidine-2,4-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1.19 g (8.0 mmol) of 5-hydroxymethylimidazo[1,2-a]pyridine in 10 ml of dichloromethane, 4.05 ml (56 mmol) of thionyl chloride was added, followed by stirring at room temperature for 1 hour, after which the solvent was distilled off. To a solution of this residue and 0.94 g (8.0 mmol) of thiazolidine-2,4-dione in 15 ml of N,N-dimethylformamide, 2.40 ml (16.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by stirring at 80° C. for 16 hours. After the reaction mixture was cooled, water was added; the mixture was extracted with ethyl acetate and dried, after which the solvent was distilled off. The residue was purified by recrystallization (solvent, chloroform/ethyl acetate/diethyl ether) to yield 247 mg (12.5%, light brown powder) of the desired product.

Workup

  1. additionwas added
  2. distillationafter which the solvent was distilled off
  3. stirringby stirring at 80° C. for 16 hours
  4. temperatureAfter the reaction mixture was cooled
  5. extractionthe mixture was extracted with ethyl acetate
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by recrystallization (solvent, chloroform/ethyl acetate/diethyl ether)

Sources & evidence

ORD record
ord-1dfb89d2f3a24e2b8e365cbaa6dc03eb
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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