Methanesulfonic Acid → HCID 9911750, compound

HRID 1591954Notes

Reaction equation

HRID 1591954 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.[CH3:26][S:27]([OH:30])(=[O:29])=[O:28]>C(#N)C>[CH3:26][S:27]([OH:30])(=[O:29])=[O:28].[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

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 77999Rosiglitazone

Product 1

HCID 9911750HCID 9911750, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl] thiazolidine-2,4-dione (3.0 g) in acetonitrile (60 ml) was heated to 60° C. Methanesulfonic acid (0.54 ml) was added and the mixture stirred at 60° C. to give a clear solution. After cooling to 21° C. the solvent was evaporated under reduced pressure, propan-2-ol (20 ml) added to the residue and the mixture stirred at 21° C. to give a white suspension. The product was collected by filtration, washed with propan-2-ol and dried under vacuum for 5 hours to give 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione methanesulfonate (3.37 g) as a white crystalline solid.

Workup

  1. customto give a clear solution
  2. temperatureAfter cooling to 21° C. the solvent
  3. customwas evaporated under reduced pressure, propan-2-ol (20 ml)
  4. additionadded to the residue
  5. stirringthe mixture stirred at 21° C.
  6. customto give a white suspension
  7. filtrationThe product was collected by filtration
  8. washwashed with propan-2-ol
  9. customdried under vacuum for 5 hours

Sources & evidence

ORD record
ord-69427da9d92144aba6ed18324546266c
Source dataset
uspto-grants-2007_11
Patent number
US07291740B2

Reaction notes

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