Acetone → maleate salt 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleate

HRID 1058091Notes

Reaction equation

HRID 1058091 reaction equation
[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:23])=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30].CC(C)=O>>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30].[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:23])=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30]

Participants

4

Reactant 3

HCID 180AcetoneHCID 77999RosiglitazoneHCID 444266Maleic Acid

Product 1

HCID 131723756maleate salt 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleateYield 138,656.703%

Procedure

800 g of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (V) and 280 mg maleic acid were dissolved in 1.3 l of acetone in 5 l three necked round bottom flask. The reaction mixture was heated to 50°-55° C. and the solution was filtered and slowly cooled to obtain 986 g of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleate (1) (yield 95%; mp 120-122° C.).

Workup

  1. temperatureThe reaction mixture was heated to 50°-55° C.
  2. filtrationthe solution was filtered
  3. temperatureslowly cooled

Sources & evidence

ORD record
ord-2dea0873f0c54247a9f0931fbd7aa41f
Source dataset
uspto-grants-2003_02
Patent number
US06515132B2

Reaction notes

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