Water → 5-{[1-(2-Chloro-3-fluoro-4-methoxyphenyl)-2-([ethylsulfanyl]methyl)-3,3,3-trifluoro-2-hydroxypropyl]amino}-7-fluoro-1H-quinolin-2-one

HRID 1191602노트

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HRID 1191602 반응식
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[CH:11]([NH:19][C:20]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][C:24](=[O:31])[NH:25]2)[C:12]1([C:15]([F:18])([F:17])[F:16])[CH2:14][O:13]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:38]([SH:40])[CH3:39].O>CN(C=O)C>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[CH:11]([NH:19][C:20]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][C:24](=[O:31])[NH:25]2)[C:12]([CH2:14][S:40][CH2:38][CH3:39])([OH:13])[C:15]([F:16])([F:17])[F:18]

참가 물질

6

반응물 4

HCID 962WaterHCID 6343EthanethiolHCID 10796Cesium carbonateHCID 462221905-{[(2-chloro-3-fluoro-4-methoxyphenyl)(2-trifluoromethyloxiranyl)methyl]amino}-7-fluoro-1H-quinolin-2-one

생성물 1

HCID 426231905-{[1-(2-Chloro-3-fluoro-4-methoxyphenyl)-2-([ethylsulfanyl]methyl)-3,3,3-trifluoro-2-hydroxypropyl]amino}-7-fluoro-1H-quinolin-2-one수율 19.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To 66 mg (0.14 mmol) 5-{[(2-chloro-3-fluoro-4-methoxyphenyl)(2-trifluoromethyl-oxiranyl)methyl]amino}-7-fluoro-1H-quinolin-2-on obtained in example 3 and 93 mg (0.29 mmol) Cs2CO3 in 0.6 ml DMF are added 16 μl (0.22 mmol) of ethyl mercaptan in DMF. The mixture is stirred vigorously for 20 hours and water is added. The aqueous layer is extracted with ethyl acetate, the organic phases washed with brine and dried over sodium sulphate. After removal of the solvent thin layer chromatography on silica gel (ethyl acetate) yields 14 mg of the title compound.

후처리

  1. extractionThe aqueous layer is extracted with ethyl acetate
  2. washthe organic phases washed with brine
  3. dry with materialdried over sodium sulphate
  4. customAfter removal of the solvent thin layer chromatography on silica gel (ethyl acetate)

출처 및 근거

ORD 기록
ord-d6d18ba9ca524f8588c8892201432586
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680117B2

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