HCID 86751688, compound → HCID 86751689, compound

HRID 1938351Notes

Reaction equation

HRID 1938351 reaction equation
[CH3:1][N:2]([CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([CH:20]=[C:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])[CH:16]=[N:17]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1.[Pt]=O>[CH3:1][N:2]([CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([CH2:20][CH:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])[CH:16]=[N:17]2)=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 86751688HCID 86751688, compound

Product 1

HCID 86751689HCID 86751689, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 312751,4-DioxaneSolvent

Procedure

The above 5-[[7-(methylphenylamino)methyl-3-quinolyl]methylene]thiazolidine-2,4-dione (164 mg, 0.47 mmol.) was dissolved in 1,4-dioxane (5 mL), and hydrogenated at room temperature for 27 hours after addition of platinum oxide (170 mg). The reaction mixture was filtered over Celite® to remove the catalyst. The residue was washed with methanol. The methanol washings and the filtrate were combined. Then, the solvent was distilled off under reduced pressure. The residue was purified by thin layer chromatography (hexane/ethyl acetate=1/1), to give the desired compound as a yellow amorphous product (39.1 mg, yield: 22%).

Workup

  1. filtrationThe reaction mixture was filtered over Celite®
  2. customto remove the catalyst
  3. washThe residue was washed with methanol
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customThe residue was purified by thin layer chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-ae6603c5bf8044f5a11d7f9045060505
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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