Water → [3-(6,7-Dimethoxy-quinolin-4-yloxy)-quinolin-2-ylmethyl]-diisopropyl-amine

HRID 228834노트

반응식

HRID 228834 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([CH3:26])=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2.[CH:27]([N-:30][CH:31]([CH3:33])[CH3:32])([CH3:29])[CH3:28].[Li+].C1C(=O)N(Br)C(=O)C1.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([CH2:26][N:30]([CH:31]([CH3:33])[CH3:32])[CH:27]([CH3:29])[CH3:28])=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2

참가 물질

6

반응물 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 2724682Lithium diisopropylamideHCID 230783726,7-Dimethoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline2회

생성물 1

HCID 23078604[3-(6,7-Dimethoxy-quinolin-4-yloxy)-quinolin-2-ylmethyl]-diisopropyl-amine수율 16%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

6,7-Dimethoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline (compound 276) (108 mg) was dissolved in tetrahydrofuran (5 ml) to prepare a solution. A lithiumdiisopropylamide/1.8 M heptane-tetrahydrofuran-ethylbenzene solution (0.3 ml) was added to the solution at −78° C., and the mixture was stirred for 10 min. N-Bromosuccimide (180 mg) was added to the reaction solution, and the mixture was stirred at room temperature for 5 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using methanol-chloroform to give the title compound (23 mg, yield 16%).

후처리

  1. customto prepare a solution
  2. stirringthe mixture was stirred at room temperature for 5 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was then washed with water
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

출처 및 근거

ORD 기록
ord-6c84389c579e4596a1de0cac9c184db1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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