Dimethyl Sulfoxide → 3-[2-(3-Oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 276951Notes

Reaction equation

HRID 276951 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:23](=[O:24])[CH:22]=[CH:21][C:20]([C:25]3[C:26]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[N:27][N:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=34)=[N:19]2)[CH2:13]1>ClCCl.C(N(CC)CC)C.C(OCC)(=O)C>[O:11]=[C:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:23](=[O:24])[CH:22]=[CH:21][C:20]([C:25]3[C:26]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[N:27][N:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=34)=[N:19]2)[CH2:13]1

Participants

7

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 226292043-[2-(3-Hydroxycyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 226292153-[2-(3-Oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 85.1%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of oxalyl chloride (160 μl) in dichloromethane (10 ml) was added dropwise in turn with dimethyl sulfoxide (210 μl), a solution of 3-[2-(3-hydroxycyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (366 mg) in dichloromethane (10 ml) and triethylamine (663 μl) at −70° C. under nitrogen atmosphere. A reaction mixture was allowed to warm to ambient temperature and diluted with ethyl acetate (100 ml), which was washed in turn with 1N-aqueous hydrochloric acid (50 ml×2), brine (50 ml), saturated sodium hydrogen carbonate in water (50 ml) and brine (50 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel eluting in turn with 30% and 50% ethyl acetate in dichloromethane. Fractions containing desired product were combined and concentrated in vacuo to give solid, which was recrystallized from ethanol to give 3-[2-(3-oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (310 mg).

Workup

  1. customat −70° C.
  2. washwas washed in turn with 1N-aqueous hydrochloric acid (50 ml×2), brine (50 ml), saturated sodium hydrogen carbonate in water (50 ml) and brine (50 ml×2)
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave a residue, which
  6. customwas chromatographed on silica gel eluting in turn with 30% and 50% ethyl acetate in dichloromethane
  7. additionFractions containing desired product
  8. concentrationconcentrated in vacuo
  9. customto give solid, which
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-3291ed17fa1b4e48bd9bf7ac8e2826a3
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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