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Water → TAK-603

HRID 1458925
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HRID 1458925 반응식
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.Cl[CH2:9][C:10]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=2)[C:17]2[C:12](=[CH:13][C:14]([O:37][CH3:38])=[C:15]([O:35][CH3:36])[CH:16]=2)[N:11]=1.O>CN(C)C=O>[CH3:36][O:35][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][C:14]=1[O:37][CH3:38])[N:11]=[C:10]([CH2:9][N:3]1[CH:7]=[N:6][CH:5]=[N:4]1)[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]2[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

생성물 1

HCID 153980TAK-603수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

Oily sodium hydride (60%, 0.323 g) was added to a solution of 1H-1,2,4-triazole (0.558 g) in N,N-dimethylformamide (30 ml), and the mixture was stirred at room temperature for 15 minutes. Then ethyl 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate(3.0 g) was added. The mixture was stirred at 80° C. for 1 hour, poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions firstly eluted with chloroform/methanol (40/1, v/v) gave ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (1.7 g, 53%) which was then recrystallized from ethyl acetate-hexane. Colorless prisms. mp. 176°-177° C.

후처리

  1. stirringThe mixture was stirred at 80° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe fractions firstly eluted with chloroform/methanol (40/1

출처 및 근거

ORD 기록
ord-aea9c2558d1347119a4e435878f0d32e
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05852039

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