Methanesulfonic Acid → HCID 9911750, compound

HRID 1591953Notes

Reaction equation

HRID 1591953 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>O1CCCC1>[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, compoundYield 113.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
4 °C

Procedure

A solution of methanesulfonic acid (0.55 g) in tetrahydrofuran (10 ml) was added to a stirred solution of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl] thiazolidine-2,4-dione (2.50 g) in tetrahydrofuran (50 ml) at 21° C. The mixture was stirred for 5 minutes and then cooled to 4° C. for a period of 16 hours. The product was collected by filtration, washed with tetrahydrofuran (10 ml) and dried under vacuum at 21° C. for 3 hours to give 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione methanesulfonate (2.95 g) as a white crystalline solid.

Workup

  1. filtrationThe product was collected by filtration
  2. washwashed with tetrahydrofuran (10 ml)
  3. customdried under vacuum at 21° C. for 3 hours

Sources & evidence

ORD record
ord-666010637b7b469991fcf57fe95ec251
Source dataset
uspto-grants-2007_11
Patent number
US07291740B2

Reaction notes

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