2-(5-(2-(Aminomethyl)-4-fluorophenoxy)-1H-indazol-1-yl)ethanol → 1-((5-fluoro-2-(1-(2-hydroxyethyl)-1H-indazol-5-yloxy)phenyl)methyl)-3-(3-(1-hydroxy-2-methylpropan-2-yl)-1-p-tolyl-1H-pyrazol-5-yl)urea

HRID 220221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220221
[OH:1][CH2:2][C:3]([C:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)[N:8]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[N:7]=1)([CH3:5])[CH3:4].[NH2:27][CH2:28][C:29]1[CH:47]=[C:46]([F:48])[CH:45]=[CH:44][C:30]=1[O:31][C:32]1[CH:33]=[C:34]2[C:38](=[CH:39][CH:40]=1)[N:37]([CH2:41][CH2:42][OH:43])[N:36]=[CH:35]2>CC(N(C)C)=O>[F:48][C:46]1[CH:45]=[CH:44][C:30]([O:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH2:41][CH2:42][OH:43])[N:36]=[CH:35]3)=[C:29]([CH2:28][NH:27][C:12]([NH:11][C:9]2[N:8]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[N:7]=[C:6]([C:3]([CH3:5])([CH3:4])[CH2:2][OH:1])[CH:10]=2)=[O:19])[CH:47]=1

Komponenten

4

Edukt 2

HCID 445421222-(5-(2-(Aminomethyl)-4-fluorophenoxy)-1H-indazol-1-yl)ethanolHCID 445422572,2,2-Trichloroethyl 3-(1-hydroxy-2-methylpropan-2-yl)-1-p-tolyl-1H-pyrazol-5-ylcarbamate

Produkt 1

HCID 252074011-((5-fluoro-2-(1-(2-hydroxyethyl)-1H-indazol-5-yloxy)phenyl)methyl)-3-(3-(1-hydroxy-2-methylpropan-2-yl)-1-p-tolyl-1H-pyrazol-5-yl)ureaAusbeute 50,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

2,2,2-Trichloroethyl 3-(1-hydroxy-2-methylpropan-2-yl)-1-p-tolyl-1H-pyrazol-5-ylcarbamate (0.010 g, 0.024 mmol) was added to a minimal amount of DMA, 2-(5-(2-(Aminomethyl)-4-fluorophenoxy)-1H-indazol-1-yl)ethanol (prepared in steps E1-E6; 0.0079 g, 0.026 mmol) and DEA (0.0084 mmol, 0.048 mmol) were added, and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated to remove the majority of DMA. The residue was purified by silica gel chromatography using 5% MeOH in ethyl acetate to provide 7 mg of the title compound. MS M+1 (573).

Aufarbeitung

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the majority of DMA
  4. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-73515eb8ae274f5584d43f63158bf037
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202899B2

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