Dichloromethane → (E)-3-[2-(2-methoxycarbonylmethylenecyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 276946Notes

Reaction equation

HRID 276946 reaction equation
[C:1](/[CH:4]=[C:5]1/[CH:6]([N:11]2[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]3[C:19]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[N:20][N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=34)=[N:12]2)[CH2:7][CH2:8][CH2:9][CH2:10]/1)([OH:3])=[O:2].S(Cl)(Cl)=O.Cl[CH2:38]Cl>>[CH3:38][O:2][C:1](/[CH:4]=[C:5]1/[CH:6]([N:11]2[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]3[C:19]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[N:20][N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=34)=[N:12]2)[CH2:7][CH2:8][CH2:9][CH2:10]/1)=[O:3]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 70155174HCID 70155174, compound

Product 1

HCID 22629241(E)-3-[2-(2-methoxycarbonylmethylenecyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

Procedure

(E)-3-[2-(2-Carboxymethylenecyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (36.8 mg) was suspended in dichloromethane and the mixture was cooled in an ice bath. To this was added thionyl chloride (0.1 ml). After the reaction mixture was stirred at room temperature for 4 hours, the solvent was evaporated in vacuo. The residue was dissolved in methanol (2 ml), and stirred at room temperature for 10 minutes. Methanol was evaporated in vacuo and the residue was partitioned between dichloromethane (10 ml) and saturated aqueous sodium bicarbonate. After an additional extraction with dichloromethane (10 ml), the combined extracts were washed with brine (10 ml), dried over anhydrous magnesium sulfate, and evaporated in vacuo. The oily residue was crystallized from ethyl acetate to give colorless crystals of (E)-3-[2-(2-methoxycarbonylmethylenecyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (36.3 mg). The spectroscopic data for this compound were identical to those for the authentic sample obtained in Example 31.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in methanol (2 ml)
  4. stirringstirred at room temperature for 10 minutes
  5. customMethanol was evaporated in vacuo
  6. customthe residue was partitioned between dichloromethane (10 ml) and saturated aqueous sodium bicarbonate
  7. extractionAfter an additional extraction with dichloromethane (10 ml)
  8. washthe combined extracts were washed with brine (10 ml)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated in vacuo
  11. customThe oily residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-7b8d102d40bd4ed8ad30c24e545ea963
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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