Réaction #73939

Équation de réaction

3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride

intermediate 1.6

3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride

DIEA

2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethanamine

→

title compound

N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide

Solvants

chloroform

DCM

Conditions de réaction

Traitement

1. 1
   Lavagewashed with NaHCO3 (50 mL)
2. 2
   ExtractionThe aqueous layer was extracted with DCM (2×50 mL)
3. 3
   Lavagethe combined organic fractions washed with water (200 mL), brine (200 mL)
4. 4
   Séchagedried over Na2SO4
5. 5
   AutreRemoving the solvent

Mode opératoire

To a solution of 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride (intermediate 1.6) (600 mg, 1.41 mmol) in chloroform (2.82 mL) was added DIEA (545.7 mg, 4.24 mmol) and 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethanamine (616.3 mg, 2.82 mmol). The reaction was stirred overnight at which point the mixture was diluted with 50 mL DCM and washed with NaHCO3 (50 mL). The aqueous layer was extracted with DCM (2×50 mL) and the combined organic fractions washed with water (200 mL), brine (200 mL), and dried over Na2SO4. Removing the solvent gave the title compound as an oil which was used without further purification.

Source