4-[4-(4-benzyl-2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-3-methyl-1-(tetra-hydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol → 4-[3-Methyl-1-(tetrahydro-pyran-2-yl)-4-(2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol

HRID 2279100Notes

Reaction equation

HRID 2279100 reaction equation
C([N:8]1[C:13]([CH3:15])([CH3:14])[CH2:12][N:11]([CH2:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[N:20]=[C:19]3[N:30]([CH:34]4[CH2:39][CH2:38][CH2:37][CH2:36][O:35]4)[N:31]=[C:32]([CH3:33])[C:18]=23)[C:10]([CH3:41])([CH3:40])[CH2:9]1)C1C=CC=CC=1>CO>[CH3:33][C:32]1[C:18]2[C:19](=[N:20][C:21]([C:23]3[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=3)=[CH:22][C:17]=2[CH2:16][N:11]2[CH2:12][C:13]([CH3:14])([CH3:15])[NH:8][CH2:9][C:10]2([CH3:41])[CH3:40])[N:30]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[N:31]=1

Participants

3

Reactant 1

HCID 1366231894-[4-(4-benzyl-2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-3-methyl-1-(tetra-hydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol

Product 1

HCID 1366231914-[3-Methyl-1-(tetrahydro-pyran-2-yl)-4-(2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenolYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

250 mg 4-[4-(4-benzyl-2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-3-methyl-1-(tetra-hydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol was dissolved in 20 ml methanol and purged with argon. 25 mg Palladium (10% on charcoal) were added and the mixture was hydrogenated at r.t. for 30 min. The catalyst was filtered off and the solvents were evaporated. 150 mg (72%) of the title compound were obtained.

Workup

  1. custompurged with argon
  2. addition25 mg Palladium (10% on charcoal) were added
  3. filtrationThe catalyst was filtered off
  4. customthe solvents were evaporated

Sources & evidence

ORD record
ord-8ebeb12a1da947a49ce8ba0461e776d8
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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