4-Bromo-2,6-difluorophenyl isocyanate → N-(4-bromo-2,6-difluorophenyl)-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide

HRID 525170ノート

反応式

HRID 525170 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([N:9]=[C:10]=[O:11])=[C:6]([F:8])[CH:7]=1.[CH:13]1([C:16]([N:18]2[CH2:22][CH2:21][C@@H:20]([CH2:23][C:24]([NH:26][NH2:27])=[O:25])[CH2:19]2)=[O:17])[CH2:15][CH2:14]1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([NH:9][C:10]([NH:27][NH:26][C:24](=[O:25])[CH2:23][C@@H:20]2[CH2:21][CH2:22][N:18]([C:16]([CH:13]3[CH2:15][CH2:14]3)=[O:17])[CH2:19]2)=[O:11])=[C:6]([F:8])[CH:7]=1

参加物

4

反応物 2

HCID 45886804-Bromo-2,6-difluorophenyl isocyanateHCID 673540782-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide

生成物 1

HCID 71087576N-(4-bromo-2,6-difluorophenyl)-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

In a round-bottom flask, 5-bromo-1,3-difluoro-2-isocyanatobenzene (1550 mg, 6.62 mmol) was dissolved in dichloromethane (10 mL) under nitrogen and cooled to −78° C. In a separate vial, 2-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide (1357 mg, 6.42 mmol) was dissolved in 10 mL of dichloromethane and then added to the cooled solution. The resultant reaction mixture was allowed to warm to room temperature and stirred for 1 h. A precipitate began to form and analysis by LCMS indicated formation of the desired product. The precipitated product was collected under vacuum filtration and washed with dichloromethane to afford the title product as a white solid (2850 mg, 99%). MS(ES)+ m/e 445.2, 447.1 [M+H]+.

後処理

  1. additionadded to the cooled solution
  2. customThe resultant reaction mixture
  3. temperatureto warm to room temperature
  4. customto form

出典と根拠

ORDレコード
ord-3ad9ae7bff614b00b5f0aca65bedabef
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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