HCID 86754256, compound → HCID 86754255, compound

HRID 582629Notes

Reaction equation

HRID 582629 reaction equation
[CH3:1][N:2]([CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[C:26]2[S:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:21][CH:20]=1)[CH2:3][C:4]1[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][C:8]=1[CH3:9].[H][H]>O1CCOCC1.[Pd]>[CH3:1][N:2]([CH2:16][CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH:26]2[S:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:23][CH:24]=1)[CH2:3][C:4]1[N:5]=[C:6]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:7][C:8]=1[CH3:9]

Participants

5

Reactant 2

HCID 86754256HCID 86754256, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86754255HCID 86754255, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

5-[4-[2-[N-methyl-N-(5-methyl-2-phenyl-4-oxazolyl)methylamino]ethoxy]phenyl methylene]thiazolidine-2,4-dione (2.5 g) obtained in example 18, was dissolved in dry 1,4-dioxane (100 ml) and was reduced with hydrogen (50 psig) in the presence of 10% palladium on charcoal (2.5 g) at ambient temperature until hydrogen uptake ceased. The solution was filtered through a bed of celite, the filter pad was washed exhaustively with dioxane and the combined filtrate was evaporated to dryness under reduced pressure to afford 2.5 g of the title compound after crystallisation from a mixture of benzene and petroleum ether.

Workup

  1. filtrationThe solution was filtered through a bed of celite
  2. washthe filter pad was washed exhaustively with dioxane
  3. customthe combined filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f27d464bd14a4864be9906f2df5b30b4
Source dataset
uspto-grants-1999_07
Patent number
US05925656

Reaction notes

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