Hydrochloric Acid → 5-[4-(N,N-Dimethylamino)phenyl]-1-isopropyl-4-(4-methoxyphenyl)methyl-3H-pyrazole-3-on hydrochloride

HRID 1365052Notes

Reaction equation

HRID 1365052 reaction equation
[BH4-].[Na+].C([O:10][C:11]1[C:15]([C:16](=O)[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[C:14]([C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[N:13]([CH:35]([CH3:37])[CH3:36])[N:12]=1)C1C=CC=CC=1.[ClH:38]>O1CCCC1>[ClH:38].[CH3:34][N:32]([C:29]1[CH:30]=[CH:31][C:26]([C:14]2[N:13]([CH:35]([CH3:36])[CH3:37])[NH:12][C:11](=[O:10])[C:15]=2[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[CH:27][CH:28]=1)[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 669711163-benzyloxy-5-[4-(N,N-dimethylamino)phenyl]-1-isopropyl-4-(4-methoxybenzoyl)-1H-pyrazole

Product 1

HCID 669710015-[4-(N,N-Dimethylamino)phenyl]-1-isopropyl-4-(4-methoxyphenyl)methyl-3H-pyrazole-3-on hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium borohydride (0.016 g) in tetrahydrofuran (4 mL) was added 3-benzyloxy-5-[4-(N,N-dimethylamino)phenyl]-1-isopropyl-4-(4-methoxybenzoyl)-1H-pyrazole (0.098 g) in tetrahydrofuran (1 mL) at 0° C., and the mixture was stirred for 1 hour. Diluted hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The residue was dissolved in methanol (5 mL), and 10% palladium-carbon powder (10 mg) and a hydrochloric acid aqueous solution (2 mol/L, 0.1 mL) were added to the solution. The mixture was stirred at room temperature under a hydrogen atmosphere for 6 hours. The insoluble material was removed by filtration and the solvent of the filtrate was removed under reduced pressure to give the title compound (0.051 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (5 mL)
  6. addition10% palladium-carbon powder (10 mg) and a hydrochloric acid aqueous solution (2 mol/L, 0.1 mL) were added to the solution
  7. stirringThe mixture was stirred at room temperature under a hydrogen atmosphere for 6 hours
  8. customThe insoluble material was removed by filtration
  9. customthe solvent of the filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-0382398016c449f2979e5d72b12c658b
Source dataset
uspto-grants-2011_02
Patent number
US07888487B2

Reaction notes

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