N-[4-(1,3-benzodioxol-5-yl)-1-benzyl-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide → N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]4-(tert-butyl)benzenesulfonamide

HRID 1368621Notes

Reaction equation

HRID 1368621 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:36][CH2:37][CH2:38][OH:39])=[N:12][N:13](CC4C=CC=CC=4)[C:14]=3[NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1.[H][H]>C(O)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:36][CH2:37][CH2:38][OH:39])=[N:12][NH:13][C:14]=3[NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:26])[CH3:27])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 22281905N-[4-(1,3-benzodioxol-5-yl)-1-benzyl-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 22281936N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]4-(tert-butyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-[4-(1,3-benzodioxol-5-yl)-1-benzyl-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide (Example 78) (15.8 g) was dissolved in acetic acid (500 ml). Under an atmosphere of nitrogen, Pearlmann's catalyst (JM type 91, 1.6 g) was added and the reaction was stirred for 48 h under 4 bars of hydrogen at 50° C. The reaction mixture was filtered on a short pad of Celite® and concentrated under reduced pressure. To the oily residue was added water (300 ml) and dichloromethane (300 ml). The phases were separated, the organic phase washed with a 5% aqueous solution of sodium bicarbonate (2×150 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was dissolved in methanol (300 ml), solid potassium carbonate (8 g) was added in one portion and the reaction mixture was stirred overnight and then concentrated under reduced pressure. Water (500 ml) was added to the resulting solid and the mixture as extracted with dichloromethane (3×500 ml). The organic fraction was dried on sodium sulfate and concentrated under reduced pressure. The red-yellow solid was re-crystallised in ethyl acetate yielding the title compound as a white solid (7.2 g)

Workup

  1. additionUnder an atmosphere of nitrogen, Pearlmann's catalyst (JM type 91, 1.6 g) was added
  2. filtrationThe reaction mixture was filtered on a short pad of Celite®
  3. concentrationconcentrated under reduced pressure
  4. additionTo the oily residue was added water (300 ml) and dichloromethane (300 ml)
  5. customThe phases were separated
  6. washthe organic phase washed with a 5% aqueous solution of sodium bicarbonate (2×150 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue was dissolved in methanol (300 ml)
  10. additionsolid potassium carbonate (8 g) was added in one portion
  11. concentrationconcentrated under reduced pressure
  12. additionWater (500 ml) was added to the resulting solid
  13. extractionthe mixture as extracted with dichloromethane (3×500 ml)
  14. customThe organic fraction was dried on sodium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customThe red-yellow solid was re-crystallised in ethyl acetate yielding the title compound as a white solid (7.2 g)

Sources & evidence

ORD record
ord-afc63cfc5c7a4cd8bebdfe6d3716bc9b
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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