HCID 11596355, compound → HCID 59769615, compound

HRID 420479Notes

Reaction equation

HRID 420479 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[N:11]([CH:17]2[CH2:19][CH2:18]2)[C:10]=1[C:20]([NH:22][CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:21])C1C=CC=CC=1.[H][H]>C(O)C.CO.[Pd]>[CH:24]1([CH2:23][NH:22][C:20]([C:10]2[N:11]([CH:17]3[CH2:19][CH2:18]3)[C:12]([CH3:16])=[CH:13][C:14](=[O:15])[C:9]=2[OH:8])=[O:21])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

6

Reactant 2

HCID 11596355HCID 11596355, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59769615HCID 59769615, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 3-(benzyloxy)-N-(cyclohexylmethyl)-1-cyclopropyl-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxamide (2.0 g, 4.8 mmol), Pd/C (10% wet, 0.45 g) in ethanol (150 mL) was hydrogenated in a Parr apparatus at 50 psi of hydrogen pressure for 16 h. The reaction mixture was filtered over a pad of Celite® and the Celite® was thoroughly washed with EtOH (25 mL). Evaporation of the solvent afforded a pale pink solid. The solid was dissolved in hot methanol, then cooled to RT as solid product precipitated out. The solid was collected by suction filtration. The mother liquor was concentrated in vacuo and the residual solid was again dissolved in hot methanol and cooled to RT to precipitate out the product, which was then collected. This process was repeated one more time. The three combined white solid fractions weighed 0.95 g (63% yield).

Workup

  1. filtrationThe reaction mixture was filtered over a pad of Celite®
  2. washthe Celite® was thoroughly washed with EtOH (25 mL)
  3. customEvaporation of the solvent
  4. customafforded a pale pink solid
  5. customprecipitated out
  6. filtrationThe solid was collected by suction filtration
  7. concentrationThe mother liquor was concentrated in vacuo
  8. dissolutionthe residual solid was again dissolved in hot methanol
  9. temperaturecooled to RT
  10. customto precipitate out the product, which
  11. customwas then collected

Sources & evidence

ORD record
ord-2234e08bf96f4a14b1a8926942c7363b
Source dataset
uspto-grants-2012_01
Patent number
US08097624B2

Reaction notes

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