Reaktion #71469

Reaktionsgleichung

propylphosphonic anhydride

5-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid

4-(4-ethylpiperazin-1-yl)-aniline

Et3N

→

title compound

5-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid [4-(4-ethyl-piperazin-1-yl)-phenyl]-amide

Lösungsmittel

DMF

EtOAc

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe aqueous layer was separated
2. 2
   Extraktionextracted with EtOAc
3. 3
   WaschenThe combined organic phase was washed with brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by trituration in EtOAc

Vorschrift

A mixture of propylphosphonic anhydride (50% in DMF, 0.41 mL, 0.70 mmol, 2 equiv), 5-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (Step 159.1) (132 mg, 0.35 mmol), 4-(4-ethylpiperazin-1-yl)-aniline (Step 1.9) (79 mg, 0.39 mmol, 1.1 equiv), DMAP (3 mg), and Et3N (0.49 mL, 3.5 mmol, 10 equiv) in DMF (3 mL), was stirred for 16 h at rt, under an argon atmosphere. The reaction mixture was diluted with EtOAc and H2O. The aqueous layer was separated and extracted with EtOAc. The combined organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by trituration in EtOAc to afford the title compound as a yellow solid: ES-MS: 564.9/566.9 [M+H]+; ta=4.45 min (System 1).

Quelle