Pyridine → HCID 22629194, compound

HRID 965368Notes

Reaction equation

HRID 965368 reaction equation
[C:1]([CH2:4][C:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=1[N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]2[C:19]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)=[N:12]1)(=O)[NH2:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C>ClCCl>[C:1]([CH2:4][C:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=1[N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]2[C:19]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)=[N:12]1)#[N:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 22629189HCID 22629189, compound

Product 1

HCID 22629194HCID 22629194, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[2-(2-carbamoylmethyl-1-cyclohexenyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (2.15 g) and pyridine (2.1 ml) in dichloromethane (25 ml) was added dropwise trifluoroacetic anhydride (1.1 ml) at 0° C. under nitrogen atmosphere. The reaction mixture was allowed to warm to room temperature and stirred for 3 hours. The resultant was poured into ethyl acetate (500 ml), washed in turn with water (100 ml×2), saturated sodium hydrogen carbonate in water (50 ml×2), 1N-aqueous hydrochloric acid (50 ml×2), brine (100 ml), saturated sodium hydrogen carbonate in water (50 ml×2) and brine (100 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (200 ml) eluting in turn with 3% and 5% ethyl acetate in dichloromethane. Fractions containing desired product were collected. Evaporation of the solvent gave a residue, which was recrystallized from a mixture of dichloromethane and n-hexane to give 3-[2-(2-cyanomethyl-1-cyclohexenyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (1.28 g).

Workup

  1. washwashed in turn with water (100 ml×2), saturated sodium hydrogen carbonate in water (50 ml×2), 1N-aqueous hydrochloric acid (50 ml×2), brine (100 ml), saturated sodium hydrogen carbonate in water (50 ml×2) and brine (100 ml×2)
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent
  4. customgave a residue, which
  5. customwas chromatographed on silica gel (200 ml)
  6. washeluting in turn with 3% and 5% ethyl acetate in dichloromethane
  7. additionFractions containing desired product
  8. customwere collected
  9. customEvaporation of the solvent
  10. customgave a residue, which
  11. customwas recrystallized from a mixture of dichloromethane and n-hexane

Sources & evidence

ORD record
ord-ab706b28d8c3404e81ea66f2b7c3291e
Source dataset
uspto-grants-1998_06
Patent number
US05773530

Reaction notes

Loading…