Dithiaoctanediol → (Z)-N-(2-Cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-(3,3-dimethylbut-1-en-1-yl)-4-methylisoxazole-3-carboxamide

HRID 1478174

Reaction equation

HRID 1478174 reaction equation
[CH:1]1([N:7]2[C:11](=[O:12])[C:10]([NH:13][C:14]([C:16]3[C:20]([CH3:21])=[C:19]([C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25])[O:18][N:17]=3)=[O:15])=[C:9]([CH3:28])[N:8]2[CH3:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(SCCO)CSCCO>CCOC(C)=O.[Pd]>[CH:1]1([N:7]2[C:11](=[O:12])[C:10]([NH:13][C:14]([C:16]3[C:20]([CH3:21])=[C:19](/[CH:22]=[CH:23]\[C:24]([CH3:26])([CH3:25])[CH3:27])[O:18][N:17]=3)=[O:15])=[C:9]([CH3:28])[N:8]2[CH3:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 78904DithiaoctanediolHCID 118511150N-(2-Cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-(3,3-dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxamide

Product 1

HCID 118511121(Z)-N-(2-Cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-(3,3-dimethylbut-1-en-1-yl)-4-methylisoxazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

N-(2-Cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-(3,3-dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxamide (Example 7, Step 3)) (30 mg, 0.075 mmol) in EtOAc (3 mL) was treated with 2,2′-(ethane-1,2-diylbis(sulfanediyl))diethanol (13.72 mg, 0.075 mmol) and Pd-5% Barium sulphate (16.02 mg, 7.53 μmol). The mixture was degassed, thoroughly refilling with nitrogen and the mixture was stirred under an atmosphere of hydrogen at room temperature overnight. Further Pd-5% Barium sulphate (16.02 mg, 7.53 μmol) was added and the reaction mixture was stirred at room temperature under an atmosphere of hydrogen for 16 hours. The resulting mixture was filtered through Celite® eluting with EtOAc and the solvent was removed under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 0-100% EtOAc in iso-hexane afforded the title compound;

Workup

  1. customThe mixture was degassed
  2. stirringthe reaction mixture was stirred at room temperature under an atmosphere of hydrogen for 16 hours
  3. filtrationThe resulting mixture was filtered through Celite®
  4. washeluting with EtOAc
  5. customthe solvent was removed under reduced pressure
  6. customThe crude material was adsorbed onto silica and purification by chromatography
  7. washeluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-e0eb9d9e3d6749e299366994d18a99ad
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Linked notes

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