Reaction #71332

Reaction equation

4-(4-{[8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonyl]-amino}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HCl

→

title compound

Yield 80.2%

8-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (4-piperazin-1-yl-phenyl)-amide

Yield 80.2%

Solvents

DCM

H2O

dioxane

Conditions

Workup

1. 1
   OtherThe aqueous layer was separated
2. 2
   Extractionextracted with DCM
3. 3
   WashThe organic phase was washed with H2O and brine
4. 4
   Dryingdried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   OtherThe residue was triturated in Et2O

Procedure

A mixture of 4-(4-{[8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonyl]-amino}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (Step 8.1) (137 mg, 0.22 mmol) and a 4 N solution of HCl in dioxane (5 mL) was stirred for 1 h at rt. The reaction mixture was diluted with DCM and H2O. The aqueous layer was separated and extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was triturated in Et2O to afford 95 mg of the title compound as a red solid: ESI-MS: 537.9/539.9 [M+H]+; tR=4.01 min (System 1).

Source