Methanesulfonic Acid → HCID 9911750, compound

HRID 1591950Notes

Reaction equation

HRID 1591950 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]>CC(C)=O>[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, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (15 g) in acetone (230 ml) was stirred and heated to reflux for 30 minutes at which point a clear solution was observed. Methanesulfonic acid (4.0 g) was added and the mixture was stirred at reflux for 5 minutes, then cooled to 40° C. and stirred until crystallisation was observed. After cooling to 21° C. the product was collected by filtration and dried under vacuum at 21° C. to provide 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione methanesulfonate (17.3 g) as a white crystalline solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes at which point a clear solution
  3. temperatureat reflux for 5 minutes
  4. stirringstirred until crystallisation
  5. temperatureAfter cooling to 21° C. the product
  6. filtrationwas collected by filtration
  7. customdried under vacuum at 21° C.

Sources & evidence

ORD record
ord-5234ebeb429a4225ae558ecc551e3036
Source dataset
uspto-grants-2007_11
Patent number
US07291740B2

Reaction notes

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