1,1'-Carbonyldiimidazole → 5-(3-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

HRID 38502

Reaction equation

HRID 38502 reaction equation
[C:1]1(=[O:10])[C:5]2=[CH:6][S:7][CH:8]=[C:4]2[C:3](=[O:9])O1.[NH2:11][C:12]1([CH3:20])[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]1=[O:19].C1N=CN(C(N2C=NC=C2)=O)C=1>C1COCC1.CN(C1C=CN=CC=1)C>[CH3:20][C:12]1([N:11]2[C:3](=[O:9])[C:4]3=[CH:8][S:7][CH:6]=[C:5]3[C:1]2=[O:10])[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]1=[O:19]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3156081H,3H-Thieno[3,4-c]furan-1,3-dioneHCID 155520363-Amino-3-methylpiperidine-2,6-dione

Product 1

HCID 597652905-(3-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dioneYield 79.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.54 g of thieno(3,4-c)furan-1,3-dione was dissolved in 20 mL of anhydrous THF, and 1.42 g of 3-amino-3-methylpiperidin-2,6-dione was added. The reaction mixture was allowed to react at room temperature for 4 h, and 2 g of CDI and a catalytic quantity of DMAP were added. The reaction mixture was allowed to reflux for 6 h during which time a solid precipitated. The reaction solution was cooled and filtered to obtain a white solid (2.2 g). MS (m/z): 278 (M)+.

Workup

  1. customto react at room temperature for 4 h
  2. temperatureto reflux for 6 h during which time a solid
  3. customprecipitated
  4. temperatureThe reaction solution was cooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-78bec2465af141378a44291e363afb91
Source dataset
uspto-grants-2013_09
Patent number
US08524742B2

Linked notes

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