Reacción #2186208

Ecuación de reacción

sodium bicarbonate

3-Benzothiazol-2-yl-7-[4-(3-hydroxy-propyl)-piperazin-1-yl]-chromen-2-one

Hünig base

tosyl chloride

→

Toluene-4-sulfonic acid 3-[4-(3-benzothiazol-2-yl-2-oxo-2H-chromen-7-yl)-piperazin-1-yl]-propyl ester

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONpoured onto ice
2. 2
   Extracciónextracted (dichloromethane, saline)
3. 3
   OtroThe organic phase is evaporated
4. 4
   Otrothe residue column chromatographed (silica gel, dichloromethane/EtOH 98:2)
5. 5
   Otroto yield
6. 6
   Otroafter evaporation
7. 7
   Secadodrying under high vacuum 73 mg (78%) desired product as a light brownish powder

Procedimiento

70 mg (0.16 mmol) 3-Benzothiazol-2-yl-7-[4-(3-hydroxy-propyl)-piperazin-1-yl]-chromen-2-one are dissolved in 15 mL dichloromethane under argon. 0.083 mL Hünig base and 10 mg DMAP are added to the stirred solution, followed by 46 mg (1.5 eq.) tosyl chloride. The reaction mixture is stirred for 20 h at room temperature, poured onto ice, treated with 2 mL aqueous sodium bicarbonate solution and extracted (dichloromethane, saline). The organic phase is evaporated and the residue column chromatographed (silica gel, dichloromethane/EtOH 98:2) to yield after evaporation and drying under high vacuum 73 mg (78%) desired product as a light brownish powder.

Fuente