2-(2-Aminoethyl)-1-methylpyrrolidine → 5-Chloro-N-{2-[2-(1-methyl-2-pyrrolidinyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-2-thiophenecarboxamide

HRID 1455676Notes

Reaction equation

HRID 1455676 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[C:18]3[C:17](=[O:19])O[C:15](=[O:20])[C:14]=3[CH:13]=[CH:12][CH:11]=2)=[O:8])=[CH:4][CH:3]=1.[CH3:21][N:22]1[CH2:26][CH2:25][CH2:24][CH:23]1[CH2:27][CH2:28][NH2:29]>O1CCOCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:18]=2[C:17](=[O:19])[N:29]([CH2:28][CH2:27][CH:23]2[CH2:24][CH2:25][CH2:26][N:22]2[CH3:21])[C:15]3=[O:20])=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 113926535-Chloro-N-(1,3-dioxo-1,3-dihydro-2-benzofuran-4-yl)-2-thiophenecarboxamide

Product 1

HCID 120748895-Chloro-N-{2-[2-(1-methyl-2-pyrrolidinyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

50 mg (0.16 mmol) of 5-chloro-N-(1,3-dioxo-1,3-dihydro-2-benzofuran-4-yl)-2-thiophenecarboxamide and 20.8 mg of (0.16 mmol) 2-(1-methyl-2-pyrrolidinyl)ethylamine are dissolved in 2 ml of dioxane and heated at reflux for 24 h. Removal of the solvent under reduced pressure gives 65 mg (97% of theory) of the desired product.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-fee35bb043ef46b98cd8463a944bec63
Source dataset
uspto-grants-2009_01
Patent number
US07482472B2

Reaction notes

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