反応式
S(Cl)(Cl)=O.O[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=1.[ClH:15].[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH2:27][NH2:28].C(N(CC)CC)C>ClCCl>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH2:27][NH:28][C:12]([C:9]1[CH:8]=[C:7]([CH2:6][Cl:15])[O:11][N:10]=1)=[O:14]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 80 °C
実験手順
Thionyl chloride (0.5 mL; 7.26 mmol) was added to a mixture of 5-(hydroxymethyl)isoxazole-3-carboxylic acid (0.207 g; 7.26 mmol) and stirred at 80° C. for 72 h. The solution was concentrated under reduced pressure and the crude material was dissolved in dichloromethane (5 mL) and added to a mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.370 g; 1.60 mmol) and triethylamine (0.524 mL; 3.62 mmol) in dichloromethane (5 mL). The resulting solution was stirred at room temperature for 20 min, concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane) to afford N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(chloromethyl)isoxazole-3-carboxamide 0.088 g (22%).
後処理
- concentrationThe solution was concentrated under reduced pressure
- dissolutionthe crude material was dissolved in dichloromethane (5 mL)
- stirringThe resulting solution was stirred at room temperature for 20 min
- concentrationconcentrated under reduced pressure
- customthe crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane)
出典と根拠
- ORDレコード
- ord-e8aeaa6de6af4bfbb528e1622eee4e5b
- 出典データセット
- uspto-grants-2016_09
- 特許番号
- US09434722B2
関連ノート
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