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 1191602ノート

反応式

HRID 1191602 の反応式
[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]

参加物

6

反応物 4

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

生成物 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-one収率 19.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d6d18ba9ca524f8588c8892201432586
出典データセット
uspto-grants-2014_03
特許番号
US08680117B2

反応ノート

読み込み中…