Hydrochloric Acid → 3-Benzyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097397Notes

Reaction equation

HRID 2097397 reaction equation
[CH2:1]([C:8]1[C:16]2[C:15](=[O:17])[NH:14][N:13]=[CH:12][C:11]=2[N:10](COCC2C=CC=CC=2)[C:9]=1[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH:34]([F:36])[F:35])=[C:29]([O:37][CH:38]2[CH2:40][CH2:39]2)[CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[H][H]>[Pd].C(O)C>[CH2:1]([C:8]1[C:16]2[C:15](=[O:17])[NH:14][N:13]=[CH:12][C:11]=2[NH:10][C:9]=1[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH:34]([F:35])[F:36])=[C:29]([O:37][CH:38]2[CH2:40][CH2:39]2)[CH:28]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66602774HCID 66602774, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1358450363-Benzyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 20 ml of ethanol solution containing 198 mg (0.364 mmol) of 3-benzyl-1-benzyloxymethyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 19-(b), then, 28 mg of 5% palladium-active carbon and 0.36 ml of 1N hydrochloric acid were added thereto, and the mixture was stirred under 1 atm hydrogen atmosphere at 50° C. for 3.8 hours. After completion of the reaction, the reaction mixture was filtered, the filtrate was concentrated under reduced pressure, 8.6 ml of methanol and 4.3 ml of 28% aqueous ammonia were added to the obtained solid and the mixture was stirred at room temperature for 1 hour. Then, the solution was concentrated under reduced pressure, water was added to the obtained concentrate, and the precipitated solid was collected by filtration. The obtained solid was washed successively with water and then with diisopropyl ether and dried under reduced pressure to obtain 128 mg of the title compound as a white solid. (Yield: 84%)

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure, 8.6 ml of methanol and 4.3 ml of 28% aqueous ammonia
  4. additionwere added to the obtained solid
  5. concentrationThen, the solution was concentrated under reduced pressure, water
  6. additionwas added to the obtained
  7. concentrationconcentrate
  8. filtrationthe precipitated solid was collected by filtration
  9. washThe obtained solid was washed successively with water
  10. dry with materialwith diisopropyl ether and dried under reduced pressure

Sources & evidence

ORD record
ord-7392a72622f24039af192386fe2088b2
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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