HCID 22902333, compound → HCID 22902351, compound

HRID 1489653Notes

Reaction equation

HRID 1489653 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[N:19](CC3C=CC=CC=3)[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=3)[CH:22]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H][H]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=3)[NH:20][N:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 22902333HCID 22902333, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22902351HCID 22902351, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4.9 g of 3-{3-[N-(2-(3,4-dimethoxyphenyl)-ethyl)-amino]-propyloxy}-2-benzyl-5-(3,4-dimethoxyphenyl)-pyrazole were dissolved in glacial acetic acid, 0.5 g of palladium on charcoal was added, and the reaction mixture was hydrogenated at 80 bar hydrogen pressure and at 80° C. for 24 hours. After removal of the catalyst by filtration, the reaction mixture was concentrated by evaporation and rendered alkaline (pH=10) with sodium hydroxide solution, and the product was extracted with ethyl acetate. The organic phase was separated, concentrated and purified by flash chromatography over silica gel. 1.1 g of 3-{3-[N-(2-(3,4-dimethoxyphenyl)-ethyl)-amino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole were obtained. The IR spectrum of the base (as film) showed bands at 1511 cm-1, 1465 cm-1, 1262 cm-1.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe reaction mixture was concentrated by evaporation
  4. extractionthe product was extracted with ethyl acetate
  5. customThe organic phase was separated
  6. concentrationconcentrated
  7. custompurified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-293dbb2e8ce843228748189b981b4a9e
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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