1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [2-(2,4-Difluoroanilino)-4,5-difluorobenzoyl]-hydrazinecarboxylic acid tert-butyl ester

HRID 729391

反応式

HRID 729391 の反応式
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:6]=1[C:7]([OH:9])=O.[C:21]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:24])[NH:22][NH2:23].C(N=C=NCCCN(C)C)C>ClCCl>[C:26]([O:25][C:21]([N:22]([C:7](=[O:9])[C:6]1[CH:10]=[C:11]([F:15])[C:12]([F:14])=[CH:13][C:5]=1[NH:4][C:3]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:2]=1[F:1])[NH2:23])=[O:24])([CH3:29])([CH3:28])[CH3:27]

参加物

5

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 149974752-(2,4-Difluoroanilino)-4,5-difluorobenzoic acid

生成物 1

HCID 69071940[2-(2,4-Difluoroanilino)-4,5-difluorobenzoyl]-hydrazinecarboxylic acid tert-butyl ester収率 72.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(2,4-difluoroanilino)-4,5-difluorobenzoic acid (Example 5, 2.18 g, 7.6 mmol) and tert-butyl carbazate (1.57 g, 11.8 mmol) in dichloromethane (30 mL) is added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (2.25 g, 11.77 mmol). After stirring for 16 hours at room temperature, the reaction mixture is diluted with dichloromethane and then washed with saturated NaHCO3, water, and brine. The organic layer is dried over Na2SO4, concentrated under vacuum, and purified via column chromatography (1:3 ethyl acetate/hexanes) to afford [2-(2,4-difluoroanilino)-4,5-difluorobenzoyl]-hydrazinecarboxylic acid tert-butyl ester as a solid (2.20 g). MS EI: m/z 400 (M+).

後処理

  1. washwashed with saturated NaHCO3, water, and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. custompurified via column chromatography (1:3 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-70015e64aaf340189e77743db6ee369f
出典データセット
uspto-grants-2009_09
特許番号
US07582627B2

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