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

HRID 2405352ノート

反応式

HRID 2405352 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-a8700821ef7e4ebb9c2c2bf0f27057a2
出典データセット
uspto-grants-2014_08
特許番号
US08802864B2

反応ノート

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