Dimethylformamide → [8-chloro-3-(4-chlorophenylsulfanyl)-4-difluoromethoxy-2-methylquinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266473노트

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HRID 2266473 반응식
[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8](=[O:26])[C:9]([S:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[C:10]([CH3:17])[NH:11]2.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[C:40](OC(=O)C)([F:42])[F:41]>O>[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:26][CH:40]([F:42])[F:41])=[C:9]([S:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[C:10]([CH3:17])=[N:11]2

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 68783252[8-chloro-3-(4-chlorophenylsulfanyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic Acid Methyl EsterHCID 86613376Chlorodifluoromethyl acetate

생성물 1

HCID 68780463[8-chloro-3-(4-chlorophenylsulfanyl)-4-difluoromethoxy-2-methylquinolin-5-yloxy]acetic Acid Methyl Ester

시약·촉매·용매 1

HCID 962Water용매

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온도
80 °C

실험 절차

A mixture of [8-chloro-3-(4-chlorophenylsulfanyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester (0.26 g), N,N-dimethylformamide (5.0 mL), potassium carbonate (0.25 g) and acetic acid chlorodifluoromethyl ester (0.13 mL) was stirred at 80° C. for 17 hour. The mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and cyclohexane (7:3 by volume) to afford title compound, 0.044 g.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of dichloromethane and cyclohexane (7:3 by volume)

출처 및 근거

ORD 기록
ord-5474c21921724986963c0cbf913c0e6d
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858640B2

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