HCID 92131115, compound → HCID 118511102, compound

HRID 1478169Notes

Reaction equation

HRID 1478169 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]4[CH2:27][CH2:26][C:25]([CH3:29])([CH3:28])[CH2:24][CH:23]=4)[O:18][N:17]=3)=[O:15])=[C:9]([CH3:30])[N:8]2[CH3:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[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]4[CH2:23][CH2:24][C:25]([CH3:28])([CH3:29])[CH2:26][CH2:27]4)[O:18][N:17]=3)=[O:15])=[C:9]([CH3:30])[N:8]2[CH3:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 92131115HCID 92131115, compound

Product 1

HCID 118511102HCID 118511102, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(2-cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-(4,4-dimethylcyclohex-1-en-1-yl)-4-methylisoxazole-3-carboxamide (Example 2.2) (40 mg, 0.094 mmol) in ethanol (20 mL) was flushed with nitrogen and treated with 10% Pd—C, 50% wet (Alfa Aesar, 38303) (14.97 mg, 0.141 mmol). The reaction mixture was stirred at room temperature under an atmosphere of hydrogen for 3 hours. The resulting mixture was filtered through Celite®, washing with ethanol followed by DCM. The filtrate was concentrated under reduced pressure and the residue was passed through a 500 mg silica-TMT cartridge, eluting with ethanol:ether (1:1). The filtrate was collected and the solvent removed under reduced pressure to afford the title compound;

Workup

  1. filtrationThe resulting mixture was filtered through Celite®
  2. washwashing with ethanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washeluting with ethanol:ether (1:1)
  5. customThe filtrate was collected
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7a95e00296354748a5adc7d924120b00
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

Loading…