反応式
C[N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][C:14]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:13]3)[CH2:4][CH2:3]1.[Cl:27]C(OC(Cl)C)=O.C(N(CC)C(C)C)(C)C>ClCCCl>[ClH:27].[C:21]1([S:18]([C:14]2[CH:15]=[N:16][C:17]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][C:8]=3[N:5]2[CH2:6][CH2:7][NH:2][CH2:3][CH2:4]2)(=[O:20])=[O:19])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1参加物
実験手順
A stirred solution of 8-(4-methyl-piperazin-1-yl)-3-phenylsulfonylquinoline (E1) (0.148 g, 0.4 mmol), 1-chloroethyl chloroformate (0.093 ml, 0.85 mmol) and N,N-diisopropylethylamine (0.148 ml, 0.85 mmol) in 1,2-dichloroethane (9 ml) was heated at reflux for 1.25 h under argon. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane, pooling fractions which contained the major component (Rf 0.9, methanol/dichloromethane 1:19). The purified material was redissolved in methanol (15 ml) and the solution was refluxed for 1 h under argon. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to a solid which was stirred with diethyl ether (5 ml) and filtered to afford the title compound (E2) (0.08 g, 0.21 mmol, 51%);
後処理
- temperatureat reflux for 1.25 h under argon
- concentrationconcentrated in vacuo to an oil
- customThe oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane, pooling fractions which
- dissolutionThe purified material was redissolved in methanol (15 ml)
- temperaturethe solution was refluxed for 1 h under argon
- temperatureThe reaction mixture was cooled to ambient temperature
- concentrationconcentrated in vacuo to a solid which
- filtrationfiltered
出典と根拠
- ORDレコード
- ord-3b50d8856611446ba3e29aa96b6acfa8
- 出典データセット
- uspto-grants-2012_08
- 特許番号
- US08236947B2
関連ノート
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