HCID 59765270, compound → 1-amino-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

HRID 38497Notes

Reaction equation

HRID 38497 reaction equation
[N+:1]([C:4]1[S:5][CH:6]=[C:7]2[C:11](=[O:12])[N:10]([CH:13]3[CH2:18][CH2:17][C:16](=[O:19])[NH:15][C:14]3=[O:20])[C:9](=[O:21])[C:8]=12)([O-])=O>C1COCC1.[Pd]>[NH2:1][C:4]1[S:5][CH:6]=[C:7]2[C:11](=[O:12])[N:10]([CH:13]3[CH2:18][CH2:17][C:16](=[O:19])[NH:15][C:14]3=[O:20])[C:9](=[O:21])[C:8]=12

Participants

4

Reactant 1

HCID 59765270HCID 59765270, compound

Product 1

HCID 597652711-amino-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dioneYield 38.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.309 g of 1-nitro-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione was dissolved in 40 mL of THF, and 0.309 g of 10% Pd/C were added. The reaction mixture was reacted under an atmosphere of hydrogen at room temperature for 4 h, filtered to remove the catalyst, evaporated to dryness. The reaction mixture was purified by silica gel column chromatography to obtain the title compound as a solid (0.108 g). 1H NMR (DMSO-d6): δ 11.00 (s, 1H), 7.62 (s, 2H), 7.19 (s, 1H), 4.91 (dd, 1H, J=3 Hz, J=3 Hz), 2.89-2.73 (m, 1H), 2.58-2.40 (m, 2H), 1.99-1.91 (m, 1H); MS (m/z): 278 (M−1)+.

Workup

  1. customThe reaction mixture was reacted under an atmosphere of hydrogen at room temperature for 4 h
  2. filtrationfiltered
  3. customto remove the catalyst
  4. customevaporated to dryness
  5. customThe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d72d3fa72f3849a08469a1dbac0c7489
Source dataset
uspto-grants-2013_09
Patent number
US08524742B2

Reaction notes

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