反応 #495202

反応方程式

N-Chlorosuccinimide

(S)-1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(6-(methylsulfonyl)pyridin-3-ylamino)pyrrolidin-2-one

→

(S)-1-(1-(3,5-dichloropyrazin-2-yl)piperidin-4-yl)-3-(6-(methylsulfonyl)pyridin-3-ylamino)pyrrolidin-2-one

収率 30.7%

溶媒

AcOH

反応条件

後処理

1. 1
   workup.WAITat 50° C. for 1 hour
2. 2
   その他Acetic acid was removed with a stream of nitrogen
3. 3
   workup.STIRRINGThe residue was vigorously stirred in a mixture of 10% Na2S2O3 (1 mL) and EtOAc (1 mL) for 40 minutes
4. 4
   その他The mixture was partitioned between EtOAc (30 mL) and saturated NaHCO3 (20 mL)
5. 5
   workup.DISSOLUTIONSolids which did not dissolve
6. 6
   ろ過were collected by filtration of the suspension through a 0.45 μm nylon membrane

実験手順

N-Chlorosuccinimide (0.013 g, 0.098 mmol) was added to a suspension of (S)-1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(6-(methylsulfonyl)pyridin-3-ylamino)pyrrolidin-2-one (0.034 g, 0.075 mmol) in AcOH (0.3 mL). The mixture was stirred at ambient temperature for 1 hour and then at 50° C. for 1 hour. Acetic acid was removed with a stream of nitrogen. The residue was vigorously stirred in a mixture of 10% Na2S2O3 (1 mL) and EtOAc (1 mL) for 40 minutes. The mixture was partitioned between EtOAc (30 mL) and saturated NaHCO3 (20 mL). Solids which did not dissolve were collected by filtration of the suspension through a 0.45 μm nylon membrane to provide (S)-1-(1-(3,5-dichloropyrazin-2-yl)piperidin-4-yl)-3-(6-(methylsulfonyl)pyridin-3-ylamino)pyrrolidin-2-one (0.011 g, 0.023 mmol, 30%). Mass spectrum (apci) m/z=485.0 (M+H) 487.0. Optical purity of the product was not determined.

出典