Methanol → 1-methyl-6-[3-(quinolin-6-ylamino)propoxy]-1H-quinolin-2-one

HRID 69031

반응식

HRID 69031 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.CO.I[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH3:29])[C:24](=[O:30])[CH:23]=[CH:22]2>ClCCl>[CH3:29][N:25]1[C:26]2[C:21](=[CH:20][C:19]([O:18][CH2:17][CH2:16][CH2:15][NH:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]=[CH:7][CH:6]=[CH:5]4)=[CH:28][CH:27]=2)[CH:22]=[CH:23][C:24]1=[O:30]

참가 물질

5

반응물 3

HCID 887MethanolHCID 113736-AminoquinolineHCID 669606076-(3-iodopropoxy)-1-methyl-1H-quinolin-2-one

생성물 1

HCID 669615471-methyl-6-[3-(quinolin-6-ylamino)propoxy]-1H-quinolin-2-one수율 48%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
60 °C

실험 절차

6-Aminoquinoline (360 mg) was added to the methanol solution (10 ml) of 6-(3-iodopropoxy)-1-methyl-1H-quinolin-2-one (172 mg) and stirred at 60° C. for 17 hours. The reaction mixture was added to ice water, and extraction with dichloromethane was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:0→4:1). The purified product was condensed under reduced pressure to give the title compound (86.4 mg) as a yellow amorphous solid.

후처리

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:0→4:1)
  4. customcondensed under reduced pressure

출처 및 근거

ORD 기록
ord-2f6374596bc5445d870c3e670a90bc45
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822453B2

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