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

HRID 2376787Notes

Reaction equation

HRID 2376787 reaction equation
[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

Participants

4

Reactant 2

HCID 12262826Isonicotinoyl chloride hydrochlorideHCID 178509219HCID 178509219, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-20ef8b8bb21348bc92916ffd8cd4e0eb
Source dataset
uspto-grants-2008_12
Patent number
US07468376B2

Reaction notes

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