Reaction #73939

Reaction equation

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

Solvents

chloroform

DCM

Conditions

Workup

1. 1
   Washwashed with NaHCO3 (50 mL)
2. 2
   ExtractionThe aqueous layer was extracted with DCM (2×50 mL)
3. 3
   Washthe combined organic fractions washed with water (200 mL), brine (200 mL)
4. 4
   Dryingdried over Na2SO4
5. 5
   OtherRemoving the solvent

Procedure

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