Mesitylene → Edaglitazone

HRID 854419Notes

Reaction equation

HRID 854419 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[C:24]2[CH:23]=[CH:22][S:21][C:20]=2[C:19]([CH:25]=[C:26]2[S:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:18][CH:17]=1.N1C=C(C(O)=O)C=C(C(O)=O)C=1.C1(C)C=C(C)C=C(C)C=1>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[C:24]2[CH:23]=[CH:22][S:21][C:20]=2[C:19]([CH2:25][CH:26]2[S:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 7947MesityleneHCID 103663,5-Pyridinedicarboxylic acidHCID 853192475-[[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]-benzo[b]thien-7-yl]methylene]-2,4-thiazolidinedione

Product 1

HCID 9825701EdaglitazoneYield 92.9%

Conditions

Temperature
167 °C

Procedure

A 100 ml, 4-necked glass flask equipped with a mechanical stirrer, a thermometer, a cooler, a dropping funnel and an argon inlet was charged under argon in sequence with 9.20 g (19.6 mmol) of 5-[[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzo[b]thien-7-yl]methylene]-2,4-thiazolidinedione, 7.84 g (29.4 mmol) of 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-, diethyl ester and 43 ml of mesitylene. The suspension was stirred at reflux (ca. 167° C.) for 6 h, then the heating bath was removed. When the resulting suspension had a temperature of ca. 85° C. 125 ml of ethanol were added. After 2 h stirring at room temperature the precipitate was isolated by filtration, the filter cake was washed with 50 ml of ethanol and dried at 56° C./1 mbar for 2 h to afford 8.46 g (92%) of 5-{[4-[2-(5-methyl-2-phenyl-oxazol-4-yl)ethoxy]benzo[b]thiophen-7-yl]methyl}-2,4-thiazolidinedione as off-white crystalline material, which according to HPLC analysis had 99.3% purity.

Workup

  1. customA 100 ml, 4-necked glass flask equipped with a mechanical stirrer
  2. customthe heating bath was removed
  3. customa temperature of ca. 85° C
  4. addition125 ml of ethanol were added
  5. stirringAfter 2 h stirring at room temperature the precipitate
  6. customwas isolated by filtration
  7. washthe filter cake was washed with 50 ml of ethanol
  8. customdried at 56° C./1 mbar for 2 h

Sources & evidence

ORD record
ord-7cec9c018ecc4eb5a2fee7aca6e2b960
Source dataset
uspto-grants-2007_08
Patent number
US07259176B2

Reaction notes

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