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

HRID 714064노트

반응식

HRID 714064 반응식
[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]

참가 물질

6

반응물 4

HCID 887MethanolHCID 8471Triethylamine2회HCID 13398949N-propylsulfamoyl chlorideHCID 718113604-(8-Amino-5,6,7,8-tetrahydro-4-isoquinolinyl)benzonitrile

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-beee2114ca484373af676d4505643951
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187429B2

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