Thionyl Chloride → N'-[3-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N,N-dimethylethane-1,2-diamine

HRID 2090241노트

반응식

HRID 2090241 반응식
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])[N:14]([CH2:15][CH2:16][CH2:17]O)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.S(Cl)(Cl)=O>C(Cl)Cl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])[N:14]([CH2:15][CH2:16][CH2:17][NH:12][CH2:11][CH2:10][N:14]([CH3:15])[CH3:13])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 684322443-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-ol

생성물 1

HCID 68432302N'-[3-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N,N-dimethylethane-1,2-diamine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of the product from step (v) (0.96 g) and thionyl chloride (10 mL) in DCM (20 mL) was heated under reflux for 6 h then evaporated under reduced pressure. The residue was dissolved in acetonitrile (20 mL) then N,N-dimethylethylenediamine (10 mL) added and the mixture heated under reflux for 24 h. The solvent was removed under reduced pressure and the residue purified by RPHPLC, yield 0.512 g.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. customthen evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in acetonitrile (20 mL)
  5. additionN,N-dimethylethylenediamine (10 mL) added
  6. temperaturethe mixture heated
  7. temperatureunder reflux for 24 h
  8. customThe solvent was removed under reduced pressure
  9. customthe residue purified by RPHPLC, yield 0.512 g

출처 및 근거

ORD 기록
ord-a6b876a359624606a34ae2bc2d260994
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436178B2

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