Ammonium formate → 5-(3,4-Dimethoxyphenyl)-2-{1-[(5-hydroxy-2-methylphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 524214Notes

Reaction equation

HRID 524214 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:41])=[C:13]([C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:27](=[O:28])[C:26]([CH3:30])([CH3:29])[C:25]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=4)=[N:24]3)[CH2:19][CH2:18]2)=[O:16])[CH:14]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd].CC(=O)OCC>[CH3:40][O:39][C:33]1[CH:32]=[C:31]([C:25]2[C:26]([CH3:30])([CH3:29])[C:27](=[O:28])[N:23]([CH:20]3[CH2:21][CH2:22][N:17]([C:15]([C:13]4[CH:14]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=4[CH3:41])=[O:16])[CH2:18][CH2:19]3)[N:24]=2)[CH:36]=[CH:35][C:34]=1[O:37][CH3:38]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 462020662-(1-{[5-(Benzyloxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 462020675-(3,4-Dimethoxyphenyl)-2-{1-[(5-hydroxy-2-methylphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a blanket of nitrogen 4.0 g of 2-(1-{[5-(benzyloxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (compound described in example 84) are dissolved in 80 ml of methanol and 0.4 g palladium on charcoal (10%) and 2.25 g ammonium formiate are added. The reaction mixture is heated to reflux or 20 min until the starting material is consumed according to TLC analysis. The mixture is filtered over a plug of celite, and the solvent is removed under reduced pressure resulting in the crude product, which is taken up in EA and washed twice with water and with brine. Crystallization from EA and PE results in the title compound.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux or 20 min until the starting material
  3. customis consumed
  4. filtrationThe mixture is filtered over a plug of celite
  5. customthe solvent is removed under reduced pressure
  6. customresulting in the crude product, which
  7. washwashed twice with water and with brine
  8. customCrystallization from EA and PE

Sources & evidence

ORD record
ord-dc5a3b433eda4961a6a9285276063863
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

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