Pyridine → N-{3-Cyano-4-[4-(5-methylisoxazol-4-ylcarbonyl)piperazin-1-yl]phenyl}-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide

HRID 1744593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744593
[CH3:1][C:2]1[O:6][N:5]=[CH:4][C:3]=1[C:7](Cl)=[O:8].N1C=CC=CC=1.[C:16]([C:18]1[CH:19]=[C:20]([NH:30][C:31]([C:33]2[CH:34]=[N:35][N:36]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:37]=2[CH3:38])=[O:32])[CH:21]=[CH:22][C:23]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)#[N:17]>O>[C:16]([C:18]1[CH:19]=[C:20]([NH:30][C:31]([C:33]2[CH:34]=[N:35][N:36]([C:39]3[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=3)[C:37]=2[CH3:38])=[O:32])[CH:21]=[CH:22][C:23]=1[N:24]1[CH2:29][CH2:28][N:27]([C:7]([C:3]2[CH:4]=[N:5][O:6][C:2]=2[CH3:1])=[O:8])[CH2:26][CH2:25]1)#[N:17]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 27599175-Methyl-1,2-oxazole-4-carbonyl chlorideHCID 22227929N-[3-cyano-4-(piperazin-1-yl)phenyl]-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide

Produkt 1

HCID 22228167N-{3-Cyano-4-[4-(5-methylisoxazol-4-ylcarbonyl)piperazin-1-yl]phenyl}-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamideAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5-Methylisoxazole-4-carbonyl chloride (1.4 g) synthesized according to the method described in J. Chem. Soc. Perkin Trans. I, pp. 1875–1879 (1988) was added to a pyridine solution (20 ml) containing N-[3-cyano-4-(piperazin-1-yl)phenyl]-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide (4 g) under ice-cooling, and the mixture was stirred for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under pressure. Diisopropyl ether was added to the obtained residue to allow crystallization. The crystals were recrystallized from hydrous dimethylformamide to give the title compound (2.9 g), melting point: 208° C.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with dilute hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the solvent was evaporated under pressure
  6. additionDiisopropyl ether was added to the obtained residue
  7. customcrystallization
  8. customThe crystals were recrystallized from hydrous dimethylformamide

Quellen und Nachweise

ORD-Eintrag
ord-7293ba7a70084518aab94ea179ea607f
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015218B1

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