6-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-methyl-piperidin-4-yl)-amide → 6-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4-methyl-piperidin-4-yl)-amide

HRID 2360689Notes

Reaction equation

HRID 2360689 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([NH:15][C:16]([C:18]2[C:19]3[C:33]([CH3:34])=[N:32][N:31]([CH:35]4[CH2:40][CH2:39][CH2:38][CH2:37][O:36]4)[C:20]=3[N:21]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[CH:23]=2)=[O:17])([CH3:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:14][C:11]1([NH:15][C:16]([C:18]2[C:19]3[C:33]([CH3:34])=[N:32][N:31]([CH:35]4[CH2:40][CH2:39][CH2:38][CH2:37][O:36]4)[C:20]=3[N:21]=[C:22]([C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)[CH:23]=2)=[O:17])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 1363597716-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-methyl-piperidin-4-yl)-amide

Product 1

HCID 1363597726-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4-methyl-piperidin-4-yl)-amideYield 66.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-(4-hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-methyl-piperidin-4-yl)-amide (136 mg) in methanol (2 mL) was added palladium (10% on charcoal, 27 mg). Argon was purged through the mixture, then the mixture was saturated with hydrogen and stirred at r.t. overnight. The catalyst was filtered off, the residue was concentrated in vacuo, the residue was re-dissolved in fresh methanol (2 mL) and fresh palladium (10% on charcoal, 27 mg) was added. The mixture was again stirred at r.t. for 1 week. The catalyst was filtered off, the residue was concentrated in vacuo to give 75 mg (66%) of the title compound.

Workup

  1. customArgon was purged through the mixture
  2. filtrationThe catalyst was filtered off
  3. concentrationthe residue was concentrated in vacuo
  4. dissolutionthe residue was re-dissolved in fresh methanol (2 mL)
  5. additionfresh palladium (10% on charcoal, 27 mg) was added
  6. stirringThe mixture was again stirred at r.t. for 1 week
  7. filtrationThe catalyst was filtered off
  8. concentrationthe residue was concentrated in vacuo

Sources & evidence

ORD record
ord-dd58aa6fa4a649818a7653b054a3a8b6
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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