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 1914142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914142
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]

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9261858d21fc4b53aa25c965231aa101
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609848B2

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