262601-94-5 → HCID 21936681, compound

HRID 1360985Notes

Reaction equation

HRID 1360985 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 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

5-Pyridin-2-ylmethylene-thiazolidine-2,4-dione (5 g) in tetrahydrofuran (300 ml) was added 10% Pd/C (1 g) and the mixture was hydrogenated at ambient pressure for 16 hours. More 10% Pd/C (5 g) was added and the mixture was hydrogenated at 50 psi for 16 hours. After filtration and evaporation in vacuo, the residue was purified by column chromatography eluting with a mixture of ethyl acetate and heptane (1:1). This afforded the title compound (0.8 g, 16%) as a solid.

Workup

  1. waitthe mixture was hydrogenated at 50 psi for 16 hours
  2. filtrationAfter filtration and evaporation in vacuo
  3. customthe residue was purified by column chromatography
  4. washeluting with a mixture of ethyl acetate and heptane (1:1)

Sources & evidence

ORD record
ord-8d82e0c1b33c4595a205d814d516f328
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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