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 872983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872983
[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]

Komponenten

8

Edukt 4

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

Produkt 1

HCID 90033637N-(2-chloro-5-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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-carb oxylic 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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6335d5b958094083bfb9b1adfb3207da
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975282B2

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