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 870459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870459
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 90032748N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d8aae68c51d246b797e470d484c78006
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969388B1

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