Isonicotinoyl chloride hydrochloride → N-[6-(4-Fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]isonicotinamide

HRID 42629

Reaktionsgleichung

Reaktionsgleichung von HRID 42629
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[C:8]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[CH:9]=2)[NH:4][N:3]=1.Cl.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1>N1C=CC=CC=1>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:7]2[N:6]=[C:5]3[NH:4][N:3]=[C:2]([NH:1][C:25](=[O:32])[C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)[C:10]3=[CH:9][C:8]=2[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:18][CH:19]=1

Komponenten

4

Edukt 2

HCID 12262826Isonicotinoyl chloride hydrochlorideHCID 178509219HCID 178509219, Verbindung

Produkt 1

HCID 68443140N-[6-(4-Fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]isonicotinamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

In a volumetric flask, 3-amino-6-(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.20 g, 0.7 mmol, obtained in example 70), isonicotinoyl chloride hydrochloride (0.12 g, 0.7 mmol, obtained in section a) and pyridine (1 mL) were introduced under argon atmosphere. This was stirred at room temperature for 2 days. It was concentrated and the residue dissolved in a mixture of CHCl3 and 1 N HCl. The phases were separated and the aqueous phase was extracted with CHCl3 (×2). The aqueous phase was basified by slow addition of 1 N NaOH. Brine was added and extracted with CHCl3 and EtOAc. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using CHCl3-MeOH mixtures of increasing polarity as eluent, to afford 98 mg of the title compound (yield: 68%).

Aufarbeitung

  1. additionwere introduced under argon atmosphere
  2. concentrationIt was concentrated
  3. dissolutionthe residue dissolved in a mixture of CHCl3 and 1 N HCl
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with CHCl3 (×2)
  6. additionThe aqueous phase was basified by slow addition of 1 N NaOH
  7. additionBrine was added
  8. extractionextracted with CHCl3 and EtOAc
  9. dry with materialThe organic phase was dried over Na2SO4
  10. concentrationconcentrated to dryness
  11. customThe crude product obtained
  12. customwas purified by chromatography on silica gel
  13. temperatureof increasing polarity as eluent

Quellen und Nachweise

ORD-Eintrag
ord-e091c3f415ff4694a42d854a996f1a6b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536194B2

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