4-(4-Benzyl-2,2-dimethyl-piperazin-1-ylmethyl)-6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine → 4-[4-(2,2-Dimethyl-piperazin-1-ylmethyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-3-fluoro-phenol

HRID 2279093Notes

Reaction equation

HRID 2279093 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27]CC4C=CC=CC=4)=[CH:23][C:22]=3[F:35])[N:18]=[C:17]3[N:36]([CH:40]4[CH2:45][CH2:44][CH2:43][CH2:42][O:41]4)[N:37]=[C:38]([CH3:39])[C:16]=23)[C:10]([CH3:47])([CH3:46])[CH2:9]1)C1C=CC=CC=1>CO>[CH3:46][C:10]1([CH3:47])[CH2:9][NH:8][CH2:13][CH2:12][N:11]1[CH2:14][C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=2[F:35])[N:18]=[C:17]2[N:36]([CH:40]3[CH2:45][CH2:44][CH2:43][CH2:42][O:41]3)[N:37]=[C:38]([CH3:39])[C:16]=12

Participants

3

Reactant 1

HCID 900140774-(4-Benzyl-2,2-dimethyl-piperazin-1-ylmethyl)-6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 1366231934-[4-(2,2-Dimethyl-piperazin-1-ylmethyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-3-fluoro-phenolYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 mg 4-(4-benzyl-2,2-dimethyl-piperazin-1-ylmethyl)-6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine was dissolved in 6 ml methanol and purged with argon. 18 mg Palladium (10% on charcoal) was added and the mixture was hydrogenated at 3 bar and r.t. for 16 h. The catalyst was filtered off and the solvents were evaporated. 130 mg (45%) of the title compound were obtained.

Workup

  1. custompurged with argon
  2. addition18 mg Palladium (10% on charcoal) was added
  3. filtrationThe catalyst was filtered off
  4. customthe solvents were evaporated

Sources & evidence

ORD record
ord-c4b670db0b174080b5621e7661a78bcc
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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