1H,3H-Thieno[3,4-c]furan-1,3-dione → 5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

HRID 38495

Reaction equation

HRID 38495 reaction equation
[C:1]1(=[O:10])[C:5]2=[CH:6][S:7][CH:8]=[C:4]2[C:3](=[O:9])O1.FC(F)(F)C(O)=O.[NH2:18][CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[NH:21][C:20]1=[O:26]>C(O)(=O)C>[O:26]=[C:20]1[CH:19]([N:18]2[C:3](=[O:9])[C:4]3=[CH:8][S:7][CH:6]=[C:5]3[C:1]2=[O:10])[CH2:24][CH2:23][C:22](=[O:25])[NH:21]1

Participants

4

Reactant 2

HCID 3156081H,3H-Thieno[3,4-c]furan-1,3-dioneHCID 53447112Trifluoroacetic acid--3-aminopiperidine-2,6-dione (1/1)

Product 1

HCID 597652875-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dioneYield 122.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.54 g thieno(3,4-c)furan-1,3-dione and 1.42 g of 3-aminopiperidine-2,6-dione trifluoroacetic acid were dissolved in 15 mL of acetic acid. The reaction mixture was refluxed overnight, cooled, and evaporated to remove the solvent. The residue was dissolved in 20 mL anhydrous THF, and 2 g of CDI, and a catalytic quantity of DMAP were added. The reaction mixture was refluxed for 6 h until a large amount of white solid precipitated. The solid was cooled and filtered to yield 1.9 g of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperaturecooled
  3. customevaporated
  4. customto remove the solvent
  5. dissolutionThe residue was dissolved in 20 mL anhydrous THF
  6. addition2 g of CDI, and a catalytic quantity of DMAP were added
  7. temperatureThe reaction mixture was refluxed for 6 h until a large amount of white solid
  8. customprecipitated
  9. temperatureThe solid was cooled
  10. filtrationfiltered

Sources & evidence

ORD record
ord-f6cc675e3aab4f3eb74c0fa0a7635bb2
Source dataset
uspto-grants-2013_09
Patent number
US08524742B2

Linked notes

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