Piperazine → 3-(6-(piperazin-1-yl)pyridin-2-yl)-5-(tetrahydro-2H-pyran-3-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1774992Notes

Reaction equation

HRID 1774992 reaction equation
F[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][CH2:20][O:19][CH2:18]4)[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[N:29]1([C:2]2[N:7]=[C:6]([C:8]3[C:16]4[C:11](=[CH:12][N:13]=[C:14]([CH:17]5[CH2:22][CH2:21][CH2:20][O:19][CH2:18]5)[CH:15]=4)[NH:10][N:9]=3)[CH:5]=[CH:4][CH:3]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 712536873-(6-Fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-5-(tetrahydro-2H-pyran-3-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712540053-(6-(piperazin-1-yl)pyridin-2-yl)-5-(tetrahydro-2H-pyran-3-yl)-1H-pyrazolo[3,4-c]pyridineYield 20%

Procedure

Following the procedure of Example 144, 3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-5-(tetrahydro-2H-pyran-3-yl)-1H-pyrazolo[3,4-c]pyridine and piperazine were reacted and consequently deprotected by the procedure of Example 131, to give a racemic mixture purified via reverse phase HPLC using a gradient of MeOH in water with 0.1% NH4OH to afford 30 mg (20%) of 3-(6-(piperazin-1-yl)pyridin-2-yl)-5-(tetrahydro-2H-pyran-3-yl)-1H-pyrazolo[3,4-c]pyridine. ESI MS m/z 365.1 (M+1).

Workup

  1. customwere reacted
  2. customto give a racemic mixture
  3. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-6049a962cb6e49cb9c2ea66f936d2c9a
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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