Methanol → (rac)-N-[4-(4-Cyanophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl]-N'-propylsulfuric diamide

HRID 714064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714064
[NH2:1][CH:2]1[C:11]2[CH:10]=[N:9][CH:8]=[C:7]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH2:20]([NH:23][S:24](Cl)(=[O:26])=[O:25])[CH2:21][CH3:22].CCN(CC)CC.CO>C(Cl)Cl>[C:16]([C:15]1[CH:14]=[CH:13][C:12]([C:7]2[C:6]3[CH2:5][CH2:4][CH2:3][CH:2]([NH:1][S:24](=[O:26])(=[O:25])[NH:23][CH2:20][CH2:21][CH3:22])[C:11]=3[CH:10]=[N:9][CH:8]=2)=[CH:19][CH:18]=1)#[N:17]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8471Triethylamine2×HCID 13398949N-propylsulfamoyl chlorideHCID 718113604-(8-Amino-5,6,7,8-tetrahydro-4-isoquinolinyl)benzonitrile

Produkt 1

HCID 71811362(rac)-N-[4-(4-Cyanophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl]-N'-propylsulfuric diamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A cooled (0° C.) solution of (rac)-4-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)benzonitrile (example 1) (62.3 mg, 250 μmol) in CH2Cl2 (3 ml) was treated with propylsulfamoyl chloride (98.5 mg, 625 μmol) in CH2Cl2 (0.6 ml) and Et3N (69.7 μL, 500 μmol). After 1 h the mixture was stirred at room temperature for 1 h, cooled down (0° C.) and treated again with Et3N (69.7 μL, 500 μmol). After ½ h at room temperature, the mixture was treated with MeOH (0.2 mL) and extracted with water/AcOEt (3×). The organic phases were dried over Na2SO4, filtered and evaporated under reduced pressure. Purification by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (1 to 3%)) and precipitation from CH2Cl2 with n-pentane gave the title compound (63 mg, 68%) as off-white powder. MS: 371.2 (M+H+).

Aufarbeitung

  1. temperaturecooled down (0° C.)
  2. waitAfter ½ h at room temperature
  3. extractionextracted with water/AcOEt (3×)
  4. dry with materialThe organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customPurification
  8. customby flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (1 to 3%)) and precipitation from CH2Cl2 with n-pentane

Quellen und Nachweise

ORD-Eintrag
ord-beee2114ca484373af676d4505643951
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187429B2

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