Acetone → Rosiglitazone Maleate

HRID 1058089

Reaction equation

HRID 1058089 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].[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[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.[CH:27](/[C:26]([OH:33])=[O:32])=[CH:28]/[C:29]([OH:31])=[O:30]

Participants

5

Reactant 3

HCID 180AcetoneHCID 77999RosiglitazoneHCID 444266Maleic Acid

Product 2

HCID 5281055Rosiglitazone MaleateHCID 131723756maleate salt 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleate

Procedure

In the final step of salt formation, rosiglitazone (V) and maleic acid were refluxed in acetone at 50° to 55° C. to obtain the maleate salt 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleate (1), namely rosiglitazone maleate in high yield of 90 to 95% with high grade purity and low moisture content to be effectively dry and free flowing so that it can easily be converted into a pharmaceutical composition.

Sources & evidence

ORD record
ord-4dc8adbb61bd4210a1a090bb75ed5a70
Source dataset
uspto-grants-2003_02
Patent number
US06515132B2

Linked notes

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