Benzyl Bromide → HCID 89586189, compound

HRID 1747797Notes

Reaction equation

HRID 1747797 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[C:17](=[O:18])[CH:16]=[CH:15][N:14]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[N:13]=3)=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[CH2:25]([N:21]1[CH2:22][CH2:23][CH2:24][CH:19]([N:14]2[CH:15]=[CH:16][C:17](=[O:18])[C:12]([C:11]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[CH:9][CH:10]=3)=[N:13]2)[CH2:20]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 58072276HCID 58072276, compound

Product 1

HCID 89586189HCID 89586189, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(1-phenyl-1H-pyrazol-5-yl)-1-pyridin-3-ylpyridazin-4(1H)-one (500 mg) in acetonitrile (5 mL) was added benzylbromide (0.19 mL) at room temperature, and the mixture was heated under reflux for 5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The obtained solution was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (10 mL), and platinum dioxide (54 mg) was added. The reaction mixture was stirred at room temperature for 24 hr under a hydrogen atmosphere (3 atm) and filtered through celite. The filtrate was concentrated under reduced pressure, and the obtained residue was diluted with ethyl acetate. The obtained solution was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (270 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washThe obtained solution was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in methanol (10 mL)
  9. additionplatinum dioxide (54 mg) was added
  10. filtrationfiltered through celite
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. additionthe obtained residue was diluted with ethyl acetate
  13. washThe obtained solution was washed with water and saturated brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. customthe solvent was evaporated under reduced pressure
  16. customThe obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-1d904741c4f64bbb9dbe63c951bb56a3
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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