262601-94-5 → HCID 21936681, compound

HRID 1745413Notes

Reaction equation

HRID 1745413 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[C:8]1[S:12][C:11](=[O:13])[NH:10][C:9]1=[O:14]>O1CCCC1.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH:8]1[S:12][C:11](=[O:13])[NH:10][C:9]1=[O:14]

Participants

4

Reactant 1

HCID 3114247262601-94-5

Product 1

HCID 21936681HCID 21936681, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-pyridin-2-ylmethylene-thiazolidine-2,4-dione (5.0 g, 0.024 mol, prepared in a similar way as described in J. Med. Chem. 41 (10), 1619–1630 (1998)) in tetrahydrofuran (300 ml) was added 10% palladium on carbon (1 g) and the resulting mixture was hydrogenated. After 50 ml of hydrogen was consumed and additional portion of 10% palladium on carbon (5 g) was added and the hydrogenation was continued at 50 psi for 16 hours. The mixture was filtered and the filtrate evaporated in vacuo. The residue was subjected to flash column chromatography (1 I silicagel) using a mixture of ethyl acetate/hexane (1:1) as eluent. Semi pure fractions were collected and the solvent evaporated in vacuo affording 0.8 g (16%) of 5-pyridin-2-ylmethyl-thiazolidine-2,4-dione as a solid.

Workup

  1. customAfter 50 ml of hydrogen was consumed
  2. additionadditional portion of 10% palladium on carbon (5 g) was added
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated in vacuo
  5. additiona mixture of ethyl acetate/hexane (1:1) as eluent
  6. customSemi pure fractions were collected
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-2bbab47e676949c3b426a65c92b5031b
Source dataset
uspto-grants-2006_03
Patent number
US07019026B1

Reaction notes

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