Réaction #157656

Équation de réaction

H2O

3-[(4-chloro-2-{[(4-chloro-2-fluorophenyl)sulfonyl]amino}phenyl)sulfanyl]propanoic acid

EDC.HCl

HOBT

N-methylethanamine

→

title compound

Rendement 83.0%

3-[(4-chloro-2-{[(4-chloro-2-fluorophenyl)sulfonyl]amino}phenyl)sulfanyl]-N-ethyl-N-methylpropanamide

Rendement 83.0%

Solvants

HCl

DMF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with EtOAc
2. 2
   LavageThe organic layer was washed with brine
3. 3
   Séchagedried over Na2SO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   AutreThe residue was purified by flash column chromatography on silica gel (10-40% EtOAc in hexane)

Mode opératoire

To a solution of 3-[(4-chloro-2-{[(4-chloro-2-fluorophenyl)sulfonyl]amino}phenyl)sulfanyl]propanoic acid (297 mg, 0.70 mmol) in DMF (2 ml) was added EDC.HCl (148 mg, 0.77 mmol), HOBT.H2O (104 mg, 0.77 mmol), and N-methylethanamine (0.30 ml, 3.5 mmol). The reaction was stirred at room temperature for 16 hours, diluted with 1M HCl, extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10-40% EtOAc in hexane) to yield the title compound (269 mg, 83%) as a mixture of amide bond cis-trans isomers.

Source