Trifluoroacetic acid → 1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxy-3-{1-[3-(trifluoromethoxy)phenyl]-1H-pyrazol-5-yl}pyridazin-4(1H)-one

HRID 1528049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528049
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:12](=[O:13])[C:11]([O:14][CH3:15])=[CH:10][N:9]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:18][C:17]=2[F:27])[N:8]=1)=O.Cl.[F:30][C:31]([F:42])([F:41])[O:32][C:33]1[CH:34]=[C:35]([NH:39][NH2:40])[CH:36]=[CH:37][CH:38]=1.C(O)(C(F)(F)F)=O>C(O)C>[F:27][C:17]1[CH:18]=[C:19]([N:22]2[CH:26]=[CH:25][CH:24]=[N:23]2)[CH:20]=[CH:21][C:16]=1[N:9]1[CH:10]=[C:11]([O:14][CH3:15])[C:12](=[O:13])[C:7]([C:5]2[N:39]([C:35]3[CH:36]=[CH:37][CH:38]=[C:33]([O:32][C:31]([F:41])([F:42])[F:30])[CH:34]=3)[N:40]=[CH:3][CH:4]=2)=[N:8]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 45046393(3-(Trifluoromethoxy)phenyl)hydrazine hydrochloride2×HCID 712721203-[3-(dimethylamino)prop-2-enoyl]-1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxypyridazin-4(1H)-one

Produkt 1

HCID 712721841-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxy-3-{1-[3-(trifluoromethoxy)phenyl]-1H-pyrazol-5-yl}pyridazin-4(1H)-oneAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Versuchsvorschrift

To a suspension of 3-[3-(dimethylamino)prop-2-enoyl]-5-methoxy-1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]pyridazin-4(1H)-one (200 mg) in ethanol (2.0 mL) was added dropwise a solution of [3-(trifluoromethoxy)phenyl]hydrazine hydrochloride (139 mg) and TFA (0.2 mL) in ethanol (2.0 mL), and the mixture was so stirred at room temperature for 24 hr. To the reaction mixture was added an ethanol solution (0.3 ml) of [3-(trifluoromethoxy)phenyl]hydrazine hydrochloride (16.7 mg), and the mixture was stirred at room temperature for 24 hr. The precipitated solid was collected by filtration. The mother liquor was concentrated, and the precipitated solid was collected by filtration. The solid was combined with the previously obtained solid, and recrystallized from acetone/water to give the title compound (96.1 mg).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 24 hr
  2. filtrationThe precipitated solid was collected by filtration
  3. concentrationThe mother liquor was concentrated
  4. filtrationthe precipitated solid was collected by filtration
  5. customrecrystallized from acetone/water

Quellen und Nachweise

ORD-Eintrag
ord-28b8fb41968f43f49bf4f2da66588fa5
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090586B2

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