HCID 54324792, compound → HCID 11725052, compound

HRID 2119923Notes

Reaction equation

HRID 2119923 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]([CH:15]=[C:16]2[S:20][C:19](=[O:21])[NH:18][C:17]2=[O:22])=[CH:13][CH:12]=1.[H][H]>[Pd].CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][CH:16]2[S:20][C:19](=[O:21])[NH:18][C:17]2=[O:22])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 54324792HCID 54324792, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11725052HCID 11725052, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-[4-(2-(2-pyrimidinylamino)ethoxy)benzylidene]-2,4-thiazolidinedione (3 g) and 10% palladium on charcoal (9 g) in DMF (70 ml) was stirred under a pressure of 200 psi of hydrogen until hydrogen uptake ceased. The mixture was filtered through diatomaceous earth, and the filter pad washed exhaustively with DMF. The combined filtrates were evaporated to dryness and the title compound (m.p. 173° C.) obtained following recrystallization from methanol.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter pad washed exhaustively with DMF
  3. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-4383c86d32af41d0aa8d49ca5bcd205b
Source dataset
uspto-grants-2004_02
Patent number
US06686475B2

Reaction notes

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