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

HRID 520689노트

반응식

HRID 520689 반응식
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.[CH3:11][N:12]1[C:16]([CH3:17])=[C:15]([C:18](O)=[O:19])[C:14](=[O:21])[N:13]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.O>[Cl:8][C:7]1[CH:6]=[C:5]([OH:9])[C:4]([F:10])=[CH:3][C:2]=1[NH:1][C:18]([C:15]1[C:14](=[O:21])[N:13]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:12]([CH3:11])[C:16]=1[CH3:17])=[O:19]

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acidHCID 112406564-Amino-5-chloro-2-fluorophenol

생성물 1

HCID 90033637N-(2-chloro-5-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide수율 53.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a suspension of 4-amino-5-chloro-2-fluorophenol (0.97 g, 6 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (1.42 g, 6.12 mmol) in DMF (20 mL) was added EDCI (0.38 mg, 7.2 mmol) and HOAT (0.16 g, 1.2 mmol). The mixture was allowed to warm up to 80° C. and stirred for 24 hours. Then H2O (200 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at 0° C. for 2 hours, then filtered to give the title compound as a light brown solid (1.2 g, 53.2%).

후처리

  1. stirringThe resulted mixture was stirred at 0° C. for 2 hours
  2. filtrationfiltered

출처 및 근거

ORD 기록
ord-c7eb2564526647e49e7117766c6509ca
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326975B2

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