HCID 86591255, compound → HCID 10225156, compound

HRID 584936Notes

Reaction equation

HRID 584936 reaction equation
[CH2:1]([NH:9][C:10]([C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[C:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>[Pd].CN(C)C=O>[CH2:1]([NH:9][C:10]([C:12]1[CH:13]=[C:14]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:23]=2)[CH:15]=[CH:16][CH:17]=1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 1

HCID 86591255HCID 86591255, compound

Product 1

HCID 10225156HCID 10225156, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

150 mg (0.35 mmol) of N-octyl-4′-(2,4-dioxo-thiazolidin-5-ylidenemethyl)biphenyl-3-carboxamide, 20 ml of dimethylformamide and 150 mg of palladium-on-charcoal (10%) are introduced into a reactor under a stream of nitrogen. The medium is heated at 80° C. and hydrogenated under a pressure of 3 atm for 5 hours. The reaction medium is filtered through Celite. The filtrate is placed in water, extracted with ethyl acetate and washed thoroughly with water. The organic phase is dried over magnesium sulfate, filtered and evaporated. The residue is chromatographed on a column of silica, eluted with a mixture of heptane and ethyl acetate (30/70). 100 mg (65%) of the expected product, with a melting point of 137-138° C., are obtained.

Workup

  1. filtrationThe reaction medium is filtered through Celite
  2. extractionextracted with ethyl acetate
  3. washwashed thoroughly with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (30/70)

Sources & evidence

ORD record
ord-14604534fa414264ba9bcae82eac892d
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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