Reacción #217616

Ecuación de reacción

3-(cis-3,5-dimethyl-1-piperazinyl)-4-(methyloxy)aniline

3-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)aniline

4-(2-thienyl)benzenesulfonyl chloride

→

title product

N-[3-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)phenyl]-4-(2-thienyl)benzenesulfonamide

Disolventes

pyridine dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with methanol (2 ml)
2. 2
   Concentraciónconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
4. 4
   Lavadowashed with water (×3)
5. 5
   Lavadowashed with methanol and 2M ammonia in methanol
6. 6
   ConcentraciónThe combined basic fractions were concentrated in vacuo
7. 7
   Otrothe resulting residue was purified by column chromatography (dichloromethane to 1:4 2M ammonia in methanol:dichloromethane)

Procedimiento

A solution of 3-(cis-3,5-dimethyl-1-piperazinyl)-4-(methyloxy)aniline (D2) (117 mg, 0.5 mmol) in pyridine:dichloromethane (1:1, 4 ml) was treated with a solution 4-(2-thienyl)benzenesulfonyl chloride (WO 9827069) (143 mg, 0.55 mmol) in dichloromethane (2 ml). The solution was stirred at room temperature for 24 hours, quenched with methanol (2 ml) and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with water (×3). The organic phase was applied to a SCX cartridge (Varian bond-elute, 5 g) and washed with methanol and 2M ammonia in methanol. The combined basic fractions were concentrated in vacuo and the resulting residue was purified by column chromatography (dichloromethane to 1:4 2M ammonia in methanol:dichloromethane) to afford the title product (E11). MS (ES+) m/e 458 [M+H]+.

Fuente