Water → Edaglitazone

HRID 1384259Notes

Reaction equation

HRID 1384259 reaction equation
[Al].O.[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][CH2:16][O:17][C:18]1[C:26]2[CH:25]=[CH:24][S:23][C:22]=2[C:21]([CH:27]=[C:28]2[S:32][C:31](=[O:33])[NH:30][C:29]2=[O:34])=[CH:20][CH:19]=1>O1CCCC1>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][CH2:16][O:17][C:18]1[C:26]2[CH:25]=[CH:24][S:23][C:22]=2[C:21]([CH2:27][CH:28]2[S:32][C:31](=[O:33])[NH:30][C:29]2=[O:34])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5359268AluminumHCID 853192475-[[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]-benzo[b]thien-7-yl]methylene]-2,4-thiazolidinedione

Product 1

HCID 9825701Edaglitazone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

10 g activated aluminium needles and 1 ml water are added to a solution of 2.03 g (4.3 mmol) 5-{4-[2-(5-Methyl-2-phenyloxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-ylmethylidene}-thiazolidine-2,4-dione (Fp. 204-207° C.) in 130 ml tetrahydrofuran. Then it is heated for 50 min. while stirring to 50° C. and the solid components are removed by filtration. The filtrate is evaporated and the residue is chromatographed on silica gel with a mixture of 88 parts by volume toluene, 10 parts by volume 2-butanone and 2 parts by volume glacial acetic acid. Yield: 1.65 g (83%), Fp. 204-206° C.

Workup

  1. temperatureThen it is heated for 50 min.
  2. customthe solid components are removed by filtration
  3. customThe filtrate is evaporated
  4. customthe residue is chromatographed on silica gel with a mixture of 88 parts by volume toluene, 10 parts by volume 2-butanone and 2 parts by volume glacial acetic acid
  5. custom204-206° C.

Sources & evidence

ORD record
ord-a4339babf4d740889636de66907740e3
Source dataset
uspto-grants-2001_07
Patent number
US06258832B1

Reaction notes

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