Reaktion #627345

Reaktionsgleichung

chloroacetyl chloride

2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine

1,8-diazabicyclo[5.4.0]undec-7-ene

→

product

Ausbeute 19.9%

2-Chloro-N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]acetamide

Ausbeute 19.9%

Lösungsmittel

ethyl acetate

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting solution was heated
2. 2
   TemperaturAfter being cooled to room temperature
3. 3
   Waschenwashed with water (50 mL×3)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was purified by column chromatography on silica gel (eluting with 25% ethyl acetate in petroleum ether)

Vorschrift

To a solution of 2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine (500 mg, 1.4 mmol) in chloroform (10 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.41 mL, 2.8 mmol) followed by chloroacetyl chloride (0.17 mL, 2.1 mmol) at room temperature. The resulting solution was heated with stirring at 70° C. for 2 hours under nitrogen. After being cooled to room temperature, the reaction was diluted with ethyl acetate (50 mL), washed with water (50 mL×3), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 25% ethyl acetate in petroleum ether) to give 120 mg of the product as an off-white solid.

Quelle