4-Chloro-3-methoxyaniline → 5-(3,4-Dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide
反応式
C[Al](C)C.CO[C:7]([CH:9]1[CH2:14][S:13][CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[NH:10]1)=[O:8].[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][C:27]=1[O:33][CH3:34]>>[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:7]([CH:9]2[CH2:14][S:13][CH2:12][CH:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)[NH:10]2)=[O:8])=[CH:28][C:27]=1[O:33][CH3:34]参加物
反応条件
- 温度
- 50 °C
実験手順
A 2.0M solution of trimethylaluminum (0.39 ml, 0.78 mmol, 3.5 equivalents) was added to a solution of 5-(3,4-dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid methyl ester (67 mg, 0.22 mmol, 1.0 equivalents) and 4-chloro-3-methoxyaniline (106 mg, 0.68 mmol, 3.0 equivalents). The solution was stirred at 50° C. for 18 hours. The reaction was quenched with 1N NaOH and extracted with dichloromethane. The dichloromethane extracts were dried with MgSO4, filtered and concentrated. The residue was purified on a 1000 micron preparative TLC. 5-(3,4-Dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide was obtained as a peach solid (71 mg, 76% yield). Analysis H1 NMR (400 MHz, CDCl3): 8.61 (1H, s), 7.58 (1H, m), 7.26 (1H, m), 6.90 (2H, m), 6.78 (1H, d), 4.04 (1H, m), 3.91 (10H, m), 2.98 (1H, m), 2.78 (2H, m), 2.59 (1H, m). MS (LC-MS): Calculated for C20H23ClN2O4S 423.11, found 423.22.
後処理
- customThe reaction was quenched with 1N NaOH
- extractionextracted with dichloromethane
- dry with materialThe dichloromethane extracts were dried with MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified on a 1000 micron preparative TLC
出典と根拠
- ORDレコード
- ord-98b259cb2faf4ca8837e87a42fc7b395
- 出典データセット
- uspto-grants-2006_07
- 特許番号
- US07081458B2
反応ノート
読み込み中…