1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 520694노트

반응식

HRID 520694 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[CH3:10][N:11]1[C:15]([CH3:16])=[C:14]([C:17](O)=[O:18])[C:13](=[O:20])[N:12]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl.O>[F:9][C:3]1[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1[NH:1][C:17]([C:14]1[C:13](=[O:20])[N:12]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:11]([CH3:10])[C:15]=1[CH3:16])=[O:18]

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acidHCID 27359194-Amino-3-fluorophenol

생성물 1

HCID 90032748N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide수율 46.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a suspension of 4-amino-3-fluorophenol (1.0 g, 7.87 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (2.19 g, 9.44 mmol) in CH2Cl2 (20 mL) were added EDCI (3.02 g, 15.7 mmol) and HOAT (0.21 g, 1.57 mmol). The reaction mixture was refluxed for 20 hours, and then cooled to rt. Water (10 mL) was added and the mixture stirred at rt overnight, then filtered and the filter cake was washed with water (5 mL), followed by purifying by a silica gel column chromatography (CH2Cl2/MeOH (v/v)=70/1) to give the title compound as a beige white solid (1.25 g, 46.6%).

후처리

  1. temperatureThe reaction mixture was refluxed for 20 hours
  2. filtrationfiltered
  3. washthe filter cake was washed with water (5 mL)
  4. customby purifying by a silica gel column chromatography (CH2Cl2/MeOH (v/v)=70/1)

출처 및 근거

ORD 기록
ord-ee2387b7165d463497d1cdae74846783
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326975B2

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