Reaktion #1435753

ord-0b42858fd1174b349b6ad7db8808e9e5

Reaktionsgleichung

COc1cc2c(cc1OC)CN(CCCN)CC2.Cl.Cl
3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-propylamine dihydrochloride
CCN(C(C)C)C(C)C
N,N-diisopropylethylamine
O=S(=O)(Cl)c1cc(Cl)c(F)cc1F
3-Chloro-4,6-difluorobenzenesulfonyl chloride
COc1cc2c(cc1OC)CN(CCCNS(=O)(=O)c1cc(Cl)c(F)cc1F)CC2
solid
Ausbeute 87.0%
COc1cc2c(cc1OC)CN(CCCNS(=O)(=O)c1cc(Cl)c(F)cc1F)CC2
5-Chloro-N-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-propyl]-2,4-difluoro-benzenesulfonamide
Ausbeute 87.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    WaschenThe resulting solution was washed with water (3×20 mL)
  2. 2
    Trocknendried over Na2SO4
  3. 3
    Sonstigeevaporated to dryness
  4. 4
    workup.DISSOLUTIONThe free base was dissolved in 2-propanol (5 mL)
  5. 5
    SonstigeThe product was crystallized in 2-propanol (5 mL)
  6. 6
    Filtrationcollected by filtration, and vacuum
  7. 7
    Sonstigedried

Vorschrift

A solution of 3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-propylamine dihydrochloride (323 mg, 1 mmol), N,N-diisopropylethylamine (517 mg, 4 mmol) in CH2Cl2(15 mL), was added 3-Chloro-4,6-difluorobenzenesulfonyl chloride (259 mg, 1.05 mmol) and was stirred overnight at room temperature. The resulting solution was washed with water (3×20 mL) and dried over Na2SO4, and evaporated to dryness. The free base was dissolved in 2-propanol (5 mL). The product was crystallized in 2-propanol (5 mL) collected by filtration, and vacuum dried to give a white solid (401 mg, 87%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07211584B2uspto-grants-2007_05