Methane → 2(1H)-Pyridinone, 5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-

HRID 466024Notes

Reaction equation

HRID 466024 reaction equation
C([C:4]1[C:5](=[O:25])[NH:6][CH:7]=[C:8]([C:10]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)[CH:9]=1)(O)=O.C>C(Cl)(Cl)Cl.CO>[O:25]=[C:5]1[CH:4]=[CH:9][C:8]([C:10]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)=[CH:7][NH:6]1

Participants

5

Reactant 2

HCID 297MethaneHCID 151581293-(3-Carboxy-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 114490702(1H)-Pyridinone, 5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-Yield 28.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

3-(3-Carboxy-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine (120 mg) was melted by an electric hot plate at 370° C. This was dissolved in a mixture of chloroform (26 ml) and methanol (13 ml), and silica gel (1 g) and charcoal (0.2 g) were added thereto and then this mixture was filtered. The solvent of the filtrate was removed and chromatographed on silica gel (3 g) with a mixture of chloroform, methanol and triethylamine (200:10:1). The fractions containing the object compound were combined and evaporated in vacuo and recrystallized from ethyl acetate to give 3-(2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine (30 mg).

Workup

  1. customwas melted by an electric hot plate at 370° C
  2. additionwere added
  3. filtrationthis mixture was filtered
  4. customThe solvent of the filtrate was removed
  5. customchromatographed on silica gel (3 g) with a mixture of chloroform, methanol and triethylamine (200:10:1)
  6. additionThe fractions containing the object compound
  7. customevaporated in vacuo
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-274e9562be3242298c0e6a1d9579d125
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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