HCID 4433548, compound → HCID 16777787, compound

HRID 1370777Notes

Reaction equation

HRID 1370777 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].[H][H]>[Pd].C(OCC)(=O)C>[NH2:8][C:7]1[C:2]([CH3:1])=[C:3]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 4433548HCID 4433548, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 16777787HCID 16777787, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The crude product from Example 1A and 10% palladium on carbon (1.4 g) were stirred vigorously in ethyl acetate (70 mL) for 24 hours under one atmosphere of hydrogen. The reaction was placed under a nitrogen atmosphere, filtered through a 1 inch pad of 1:1 Celite:silica gel eluting with ethyl acetate and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, ethyl acetate) to provide the title compound as a brown solid (11.06 g, 84%).

Workup

  1. filtrationfiltered through a 1 inch pad of 1:1 Celite
  2. concentrationsilica gel eluting with ethyl acetate and the filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-d4fde4ead1c447ada904e8447ddd7124
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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