Reaction #738823

Reaction equation

3-(S)-Amino-1-(4-chloroquinolin-6-ylmethyl)-pyrrolidin-2-one hydrochloride

triethylamine

benzothiophene-2-sulfonyl chloride

→

title compound

Yield 60.5%

Benzothiophene-2-sulfonic acid [1-(4-chloroquinolin-6-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide

Yield 60.5%

Solvents

CH3CN

Conditions

Workup

1. 1
   Concentrationup then concentrated to dryness
2. 2
   OtherThe crude product is purified by column chromatography
3. 3
   Washeluting with 2-10% MeOH/CH2Cl2

Procedure

3-(S)-Amino-1-(4-chloroquinolin-6-ylmethyl)-pyrrolidin-2-one hydrochloride (0.12 g, 0.38 mmol) is suspended in 15 mL CH3CN. To this solution is added triethylamine (110 mL, 0.79 mmol) followed by benzothiophene-2-sulfonyl chloride (0.094 g, 0.40 mmol). The mixture is stirred overnight at room temperature, subjected to aqueous work up then concentrated to dryness. The crude product is purified by column chromatography eluting with 2-10% MeOH/CH2Cl2 to give the title compound (0.11 g, 0.23 mmol) as an off-white solid.

Source