HCID 54324792, compound → HCID 11725052, compound

HRID 441028Notes

Reaction equation

HRID 441028 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-241474041ac44128bf253ca67c2bb2ab
Source dataset
uspto-grants-1996_05
Patent number
US05521201

Reaction notes

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