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

HRID 703984
Notes
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Reaction equation

HRID 703984 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-1acd818055c84c1c932bebe81937c240
Source dataset
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04985444

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes