1,3-dimethyl-N-{3-[(5-nitropyridin-2-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide → N-{3-[(5-aminopyridin-2-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874380

Reaktionsgleichung

Reaktionsgleichung von HRID 1874380
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][N:18]=3)[CH:11]=2)=[O:8])=[CH:5][C:4]([CH3:26])=[N:3]1>CO.[C].[Pd]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:12]2[CH:11]=[C:10]([NH:9][C:7]([C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:26])[CH:5]=3)=[O:8])[CH:15]=[CH:14][CH:13]=2)=[N:18][CH:19]=1

Komponenten

4

Edukt 1

HCID 577493821,3-dimethyl-N-{3-[(5-nitropyridin-2-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide

Produkt 1

HCID 57749235N-{3-[(5-aminopyridin-2-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1,3-dimethyl-N-{3-[(5-nitropyridin-2-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide (2.26 g, 6.40 mmol) in methanol (20 mL) was added palladium carbon (50% water-containing product, 200 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 5 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was collected by filtration and washed with ethyl acetate-hexane to give the title compound (1.77 g, 86%) as a white solid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationThe residue was collected by filtration
  4. washwashed with ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-a322993408ae44af9bbd740ea8b41f43
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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