Methanesulfonic Acid → HCID 9911750, compound

HRID 1591956Notes

Reaction equation

HRID 1591956 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(O)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 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (12.0 g) and propan-2-ol (360 ml) was stirred and heated to reflux for 10 minutes at which point a clear solution was observed. Methanesulfonic acid (4.04 ml) was added and the stirred reaction mixture cooled to 75° C., seeded with the product of Example 6 and then cooled to 21° C. over a period of approximately 1 hour. The solid was collected by filtration, washed with propan-2-ol (50 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 (13.8 g) as a white crystalline solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 10 minutes at which point a clear solution
  3. customthe stirred reaction mixture
  4. temperaturecooled to 21° C. over a period of approximately 1 hour
  5. filtrationThe solid was collected by filtration
  6. washwashed with propan-2-ol (50 ml)
  7. customdried under vacuum for 16 hours

Sources & evidence

ORD record
ord-2a43d45dd7114b38bddb050ff21415d2
Source dataset
uspto-grants-2007_11
Patent number
US07291740B2

Reaction notes

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