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Water → 3-[4-(Imidazo[1,2-a]pyridin-5-ylsulfinyl)butyl]thiazolidine-2,4-dione

HRID 357137
Notes
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Reaction equation

HRID 357137 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[CH:10][CH:9]=1)=[O:7].[S:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23].C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[N:16]1[CH:15]=[CH:14][N:13]2[C:8]([S:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:19]3[C:20](=[O:22])[CH2:21][S:17][C:18]3=[O:23])=[O:7])=[CH:9][CH:10]=[CH:11][C:12]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 5437ThiazolidinedioneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 189368535-(4-Chlorobutylsulfinyl)imidazo[1,2-a]pyridine

Product 1

HCID 189367953-[4-(Imidazo[1,2-a]pyridin-5-ylsulfinyl)butyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.51 g (2.0 mmol) of 5-(4-chlorobutylsulfinyl)imidazo[1,2-a]pyridine and 0.355 g (2.0 mmol) of thiazolidine-2,4-dione in 10 ml of N,N-dimethylformamide, 0.30 ml (2.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by heating at 80° C. for 16 hours. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform→chloroform/methanol=50/1) to yield 0.33 g (49.0%, light yellow oily substance) of the desired product.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. distillationafter which the solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent, chloroform→chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-cc3e941c7e3f489cb1ab78c7c7ec8ee8
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05840732

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes