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

HRID 729391

반응식

HRID 729391 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-70015e64aaf340189e77743db6ee369f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582627B2

연결된 노트

불러오는 중…