Ethyl isocyanate → HCID 89846368, 화합물

HRID 714065노트

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HRID 714065 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]([N:22]=[C:23]=[O:24])[CH3:21].CCN(CC)CC.OP([O-])(O)=O.[K+]>C(Cl)Cl.CO>[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][C:23]([NH:22][CH2:20][CH3:21])=[O:24])[C:11]=3[CH:10]=[N:9][CH:8]=2)=[CH:19][CH:18]=1)#[N:17]

참가 물질

7

반응물 4

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 516951Monobasic potassium phosphateHCID 718113604-(8-Amino-5,6,7,8-tetrahydro-4-isoquinolinyl)benzonitrile

생성물 1

HCID 89846368HCID 89846368, 화합물수율 80%

시약·촉매·용매 2

HCID 887Methanol용매HCID 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 (5 mL) was treated with ethyl isocyanate (51.6 μL, 625 μmol) in CH2Cl2 (0.6 mL) and Et3N (69.7 μL, 500 μmol). After ½ h the solution was stirred at room temperature for 1 h and treated with MeOH (0.2 mL). The reaction mixture was poured on aq. 10% KH2PO4 solution followed by extraction with AcOEt (3×). The organic phases were washed once with aq. sat. NaCl solution. The combined organic phases were dried (Na2SO4), filtered and purified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (1 to 3%)). Precipitation from CH2Cl2 with n-pentane gave the title compound (64 mg, 80%) as off-white powder. MS: 321.2 (M+H+).

후처리

  1. extractionfollowed by extraction with AcOEt (3×)
  2. washThe organic phases were washed once with aq. sat. NaCl solution
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. custompurified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (1 to 3%))
  6. customPrecipitation from CH2Cl2 with n-pentane

출처 및 근거

ORD 기록
ord-1b7025e9576d4572ba0f7ba2cf6b93c0
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187429B2

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