Pyridine → N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874322

Reaktionsgleichung

Reaktionsgleichung von HRID 1874322
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=1.N1C=CC=CC=1.[CH3:22][N:23]1[C:27]([C:28](Cl)=[O:29])=[CH:26][C:25]([CH3:31])=[N:24]1>O1CCCC1.O>[NH2:12][C:9]1[N:10]=[CH:11][C:6]([O:5][C:4]2[CH:3]=[C:2]([NH:1][C:28]([C:27]3[N:23]([CH3:22])[N:24]=[C:25]([CH3:31])[CH:26]=3)=[O:29])[CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:8]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 577491665-(3-Aminophenoxy)pyridin-2-amine

Produkt 1

HCID 57749234N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamideAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 5-(3-aminophenoxy)pyridin-2-amine (975 mg, 4.85 mmol) and pyridine (410 μL, 5.09 mmol) in tetrahydrofuran (10 mL) was added dropwise with stirring under ice-cooling a solution of 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (807 mg, 5.09 mmol) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with water, extracted with ethyl acetate (×3), and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20→40/100) and recrystallized from ethyl acetate-hexane to give the title compound (964 mg, 61%) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionextracted with ethyl acetate (×3)
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20→40/100)
  8. customrecrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-6d2bdc40125d4c688e4d52cae12fd48c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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