Toluene → (S)-1-(7-Fluoro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethylamine

HRID 243204노트

반응식

HRID 243204 반응식
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:20]2[C:21]3[C:16]([CH2:17][CH2:18][CH2:19]2)=[C:15]([F:22])[CH:14]=[CH:13][C:12]=3[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[F:22][C:15]1[CH:14]=[CH:13][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:20]3[C:21]=2[C:16]=1[CH2:17][CH2:18][CH2:19]3

참가 물질

5

반응물 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 68157547[(S)-1-(7-Fluoro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethyl]carbamic acid tert-butyl ester

생성물 1

HCID 68157923(S)-1-(7-Fluoro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethylamine수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To an ice-cooled solution of [(S)-1-(7-fluoro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethyl]carbamic acid tert-butyl ester (78 mg, 0.244 mmol) in DCM (4 mL) was added TFA (1.3 mL) and the mixture was stirred at RT for 1.5 h. Toluene was added and volatiles were removed under reduced pressure, the resulting residue was dissolved in MeOH and loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product was eluted with 0.5M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo affording the title compound as a colourless gum (49.5 mg, 93%). LCMS (Method B): RT 1.78 min [M+H]+ 220

후처리

  1. customvolatiles were removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in MeOH
  3. washThe cartridge was washed with MeOH
  4. washthe product was eluted with 0.5M NH3/MeOH
  5. additionThe product containing fractions
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2266f7fb325a494ca5e29059a59225ee
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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