Methanesulfonic Acid → HCID 9911750, compound

HRID 1591955Notes

Reaction equation

HRID 1591955 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1>C(OCC)(=O)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 77999Rosiglitazone

Product 1

HCID 9911750HCID 9911750, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
21 °C

Procedure

Methanesulfonic acid (0.54 ml) was added to a mixture of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (3.0 g) and ethyl acetate (60 ml) and the reaction mixture stirred and heated to reflux to give a suspension. After cooling to 21° C. the product was collected by filtration, washed with ethyl acetate (10 ml) and dried under vacuum for 16 hours to give 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione methanesulfonate (3.73 g) as a white crystalline solid.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customto give a suspension
  4. filtrationwas collected by filtration
  5. washwashed with ethyl acetate (10 ml)
  6. customdried under vacuum for 16 hours

Sources & evidence

ORD record
ord-e8c63a92f5144a2d9e3cdded6a5fa641
Source dataset
uspto-grants-2007_11
Patent number
US07291740B2

Reaction notes

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