Diethyl Ether → HCID 9911750, compound

HRID 1591952Notes

Reaction equation

HRID 1591952 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)C>C(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

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 6395Methanesulfonic AcidHCID 77999Rosiglitazone

Product 1

HCID 9911750HCID 9911750, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
21 °C

Procedure

Methanesulfonic acid (2.3 ml) was added to a stirred suspension of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (12.0 g) in ethanol (100 ml) at 21° C. The reaction mixture was heated to reflux for 30 minutes then cooled to 21° C. Diethyl ether (100 ml) was added and the reaction heated to reflux for 1 hour, then cooled to 21° C. The reaction was heated to reflux, diethyl ether (50 ml) was added and stirred for 30 minutes, cooled to 21° C. over approximately 1 hour, then stirred for 16 hours at 21° C. The product was collected by filtration and dried under vacuum to afford 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione methanesulfonate (14.8 g) as a white crystalline solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethe reaction heated
  4. temperatureto reflux for 1 hour
  5. temperaturecooled to 21° C
  6. temperatureThe reaction was heated
  7. temperatureto reflux
  8. temperaturecooled to 21° C. over approximately 1 hour
  9. stirringstirred for 16 hours at 21° C
  10. filtrationThe product was collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-506e201af8ce43c094307a615c77b7f7
Source dataset
uspto-grants-2007_11
Patent number
US07291740B2

Reaction notes

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