Dimethylformamide → 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamide

HRID 872989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872989
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[C:13](=[O:25])[N:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:15]([CH3:18])[C:16]=1[CH3:17])=[O:11].CC([O-])(C)C.[K+].CN(C=O)C.Cl[C:38]1[CH:43]=[CH:42][N:41]=[C:40]([C:44]([NH2:46])=[O:45])[CH:39]=1>CCOC(C)=O.O>[CH3:18][N:15]1[C:16]([CH3:17])=[C:12]([C:10]([NH:9][C:3]2[CH:4]=[CH:5][C:6]([O:8][C:38]3[CH:43]=[CH:42][N:41]=[C:40]([C:44]([NH2:46])=[O:45])[CH:39]=3)=[CH:7][C:2]=2[F:1])=[O:11])[C:13](=[O:25])[N:14]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 3035434-Chloropyridine-2-carboxamideHCID 23665647Potassium tert-butoxideHCID 90032748N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Produkt 1

HCID 730510744-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamideAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (300 mg, 0.879 mmol) and t-BuOK (118 mg, 1.05 mmol) was added DMF (2.5 mL). The resulted mixture was stirred at rt for 30 minutes, then 4-chloropicolinamide (165 mg, 1.05 mmol) was added. The mixture was heated at 120° C. for 5 hours, then cooled to rt, and H2O (50 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at rt overnight. Filtered and the precipitation was washed with water (5 mL) to give the title compound as a dark brown solid (370 mg, 91.2%).

Aufarbeitung

  1. temperatureThe mixture was heated at 120° C. for 5 hours
  2. temperaturecooled to rt
  3. stirringThe resulted mixture was stirred at rt overnight
  4. filtrationFiltered
  5. customthe precipitation
  6. washwas washed with water (5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-3a7428f05d894e0ca65b852acbb2dd0e
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975282B2

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