Diisopropylethylamine → N-(4-bromo-2,3-difluorophenyl)-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide
反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[C:3]=1[F:10].Cl[C:12](Cl)([O:14]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(C(C)C)C(C)C.[CH:32]1([C:35]([N:37]2[CH2:41][CH2:40][C@@H:39]([CH2:42][C:43]([NH:45][NH2:46])=[O:44])[CH2:38]2)=[O:36])[CH2:34][CH2:33]1>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:12]([NH:46][NH:45][C:43](=[O:44])[CH2:42][C@@H:39]2[CH2:40][CH2:41][N:37]([C:35]([CH:32]3[CH2:34][CH2:33]3)=[O:36])[CH2:38]2)=[O:14])=[C:4]([F:9])[C:3]=1[F:10]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -78 °C
実験手順
To a round bottom flask, 4-bromo-2,3-difluoroaniline (2 g, 9.62 mmol) and triphosgene (0.999 g, 3.37 mmol) were added under nitrogen and cooled to −78° C. Dichloromethane (40 mL) was added followed by the slow addition of Hunig's base (3.36 mL, 19.23 mmol). The reaction was allowed to warm to room temperature and analysis by LCMS indicated desired intermediate formation. The solution was re-cooled to −78° C. and 2-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide (1.051 g, 4.97 mmol) in dichloromethane (10 mL) was added. The solution was allowed to warm to room temperature, and analysis by LCMS indicated desired product formation. After 2 h of stirring at room temperature and blowing nitrogen gently over the solution, the desired product began to precipitate and was collected by filtration and dried via vacuum filtration to afford the title product (1400 mg, 63%). MS(ES)+ m/e 445.1, 447.1 M+H]+.
後処理
- temperatureto warm to room temperature
- temperatureThe solution was re-cooled to −78° C.
- temperatureto warm to room temperature
出典と根拠
- ORDレコード
- ord-f614757247ba426ca625eaf9e53478ab
- 出典データセット
- uspto-grants-2014_08
- 特許番号
- US08802864B2
反応ノート
読み込み中…