Rosiglitazone → Rosiglitazone Maleate

HRID 2244601

Reaction equation

HRID 2244601 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]>C(O)C>[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

4

Reactant 2

HCID 77999RosiglitazoneHCID 444266Maleic Acid

Product 1

HCID 5281055Rosiglitazone MaleateYield 79.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Rosiglitazone maleate was prepared according to the disclosure of WO 94/05659, in which 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (470 gms) and maleic acid (137 gms) were dissolved in ethanol (4 ltrs) at boiling. The hot solution was filtered via diatomaceous earth and was then allowed to cool slowly with gentle agitation. After leaving in a refrigerator at 0-5° C. for several hours, the maleate salt was filtered off, washed with ethanol and dried in vacuum at 50° C. to give 446 gms of rosiglitazone maleate as provided by WO 94/05659. The product was characterized as Form-B by XRD & IR, as can be seen by reference to FIGS. 3 and 4 respectively.

Workup

  1. customRosiglitazone maleate was prepared
  2. filtrationThe hot solution was filtered via diatomaceous earth
  3. temperatureto cool slowly with gentle agitation
  4. customAfter leaving in a refrigerator at 0-5° C. for several hours
  5. filtrationthe maleate salt was filtered off
  6. washwashed with ethanol
  7. customdried in vacuum at 50° C.

Sources & evidence

ORD record
ord-368b645d364b48558588905343521725
Source dataset
uspto-grants-2010_03
Patent number
US07678916B2

Linked notes

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