Diisopropylethylamine → N-(4-bromo-2,5-difluorophenyl)-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide
反応式
[Br:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.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[C:8]([F:9])=[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:10])[CH:3]=1参加物
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-2,5-difluoroaniline (2 g, 9.62 mmol) and triphosgene (0.999 g, 3.37 mmol) were added under nitrogen and the mixture was 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 room temperature. Analysis by LCMS indicated desired intermediate formation. The solution was re-cooled to −78° C. and 2-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide (1.219 g, 5.77 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 the desired product began to precipitate out of solution and was collected by filtration and dried via vacuum filtration to afford the title product as a white solid (1340 mg, 62%). MS(ES)+ m/e 445.1, 446.9 M+H]+.
後処理
- customwas allowed 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-7d6f70022ee54876a0fd6ce90b492381
- 出典データセット
- uspto-grants-2016_05
- 特許番号
- US09340529B2
反応ノート
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