Water → 1-methylamino-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

HRID 1927141Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]2[C:9](=[O:10])[N:8]([CH:11]3[CH2:16][CH2:15][C:14](=[O:17])[NH:13][C:12]3=[O:18])[C:7](=[O:19])[C:6]=12.[CH3:20]I.O>CN(C=O)C>[CH3:20][NH:1][C:2]1[S:3][CH:4]=[C:5]2[C:9](=[O:10])[N:8]([CH:11]3[CH2:16][CH2:15][C:14](=[O:17])[NH:13][C:12]3=[O:18])[C:7](=[O:19])[C:6]=12

Participants

Conditions

Temperature: 80 °C

Procedure

0.084 g of 1-amino-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione was dissolved in 10 mL of DMF, and 0.5 mL of methyl iodide were added. The reaction mixture was heated to 80° C., allowed to react at that temperature for 6 h, cooled, and 100 mL of water were added. The reaction solution was extracted with ethyl acetate (3×30 mL). The organic phases were combined, washed with 30 mL of and 30 mL of brine, dried over anhydrous MgSO4, filtered, and evaporated to dryness. The remaining residue was purified on silica gel column chromatography to yield a solid (0.033 g). MS (m/z): 292 (M−1)+.

Workup

customto react at that temperature for 6 h
temperaturecooled
extractionThe reaction solution was extracted with ethyl acetate (3×30 mL)
washwashed with 30 mL of and 30 mL of brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customevaporated to dryness
customThe remaining residue was purified on silica gel column chromatography

Sources & evidence

ORD record: ord-853dcb6603e84faa9250644a84f16c64
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183260B2

Reaction notes

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