3-cyclopentyl-N-(5-isopropylisoxazol-4-yl)-2-[4-(methylsulfonyl)phenyl]propanamide → 1-(2-{2-cyclopentyl-1-[4-(methylsulfonyl)phenyl]ethyl}-1H-imidazol-5-yl)-2-methylpropan-1-one

HRID 1881957Notes

Reaction equation

HRID 1881957 reaction equation
[CH:1]1([CH2:6][CH:7]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[C:8]([NH:10][C:11]2[CH:12]=[N:13][O:14][C:15]=2[CH:16]([CH3:18])[CH3:17])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[C].[Pd]>[CH:1]1([CH2:6][CH:7]([C:8]2[NH:10][C:11]([C:15](=[O:14])[CH:16]([CH3:18])[CH3:17])=[CH:12][N:13]=2)[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 593312733-cyclopentyl-N-(5-isopropylisoxazol-4-yl)-2-[4-(methylsulfonyl)phenyl]propanamide

Product 1

HCID 593312831-(2-{2-cyclopentyl-1-[4-(methylsulfonyl)phenyl]ethyl}-1H-imidazol-5-yl)-2-methylpropan-1-oneYield 50%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution (40 mL) of 3-cyclopentyl-N-(5-isopropylisoxazol-4-yl)-2-[4-(methylsulfonyl)phenyl]propanamide (2.50 g) in ethanol was added 10% palladium carbon (containing 50% water, 0.500 g) and the mixture was stirred under hydrogen atmosphere (5 atm) for 4 hr. The reaction mixture was filtered to remove the catalyst, sodium hydroxide (0.261 g) was added to the filtrate, and the mixture was heated under reflux for 1 hr. To the reaction mixture was added ammonium chloride (0.430 g), and the mixture was cooled to room temperature, and stirred at room temperature for 16 hr. The reaction solution was concentrated, the obtained residue was suspended in acetone, and the suspension was filtered to remove insoluble materials. The filtrate was concentrated, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-100:0, volume ratio), and recrystallized from ethyl acetate-hexane to give the title compound (1.20 g, yield 50%) as colorless crystals. melting point 171-172° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst, sodium hydroxide (0.261 g)
  3. additionwas added to the filtrate
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 1 hr
  6. additionTo the reaction mixture was added ammonium chloride (0.430 g)
  7. stirringstirred at room temperature for 16 hr
  8. concentrationThe reaction solution was concentrated
  9. filtrationthe suspension was filtered
  10. customto remove insoluble materials
  11. concentrationThe filtrate was concentrated
  12. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-100:0, volume ratio)
  13. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-17f7a9f2f5bd4fb88a139b837d08c940
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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