4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxy-N-(4-methoxy-2-methylaminophenyl)acetamide → Rivoglitazone hydrochloride

HRID 1061125Notes

Reaction equation

HRID 1061125 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:29]=[CH:28][C:12]([O:13][CH2:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=3[NH:26][CH3:27])=O)=[CH:11][CH:10]=2)[S:3]1.[ClH:30].CO>CO>[ClH:30].[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]2[N:17]=[C:15]([CH2:14][O:13][C:12]3[CH:28]=[CH:29][C:9]([CH2:8][CH:4]4[S:3][C:2](=[O:1])[NH:6][C:5]4=[O:7])=[CH:10][CH:11]=3)[N:26]([CH3:27])[C:19]=2[CH:20]=1

Participants

4

Reactant 2

HCID 98019434-(2,4-dioxothiazolidin-5-ylmethyl)phenoxy-N-(4-methoxy-2-methylaminophenyl)acetamideHCID 21893726Hydrochloride methanol

Product 1

HCID 9889104Rivoglitazone hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxy-N-(4-methoxy-2-methylaminophenyl)acetamide (3.0 g) in methanol (46 ml) was added 2 mol/l hydrogen chloride-methanol (14 ml) and the mixture was heated under reflux for 4 hours. The reaction mixture was cooled to 40° C. and stirred at the same temperature for 1 hour. At the end of this time the reaction mixture was cooled to 25° C. and the precipitated crystals were filtered to give the title compound (2.9 g, yield 92%). Melting point, IR spectrum and NMR spectrum of this compound are substantially identical with those of the compound obtained in Example 5.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAt the end of this time the reaction mixture was cooled to 25° C.
  4. filtrationthe precipitated crystals were filtered

Sources & evidence

ORD record
ord-bd763fa5ac4d41798527e82bfb881d87
Source dataset
uspto-grants-2003_02
Patent number
US06525220B2

Reaction notes

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