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Piperazin-2-one → 4-(6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-2-one

HRID 1775079
Notes
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Reaction equation

HRID 1775079 reaction equation
F[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[N:10]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[NH:31]1[CH2:36][CH2:35][NH:34][CH2:33][C:32]1=[O:37]>N1C=CC=CC=1>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:14]2[CH:15]=[C:16]3[C:8]([C:6]4[N:7]=[C:2]([N:34]5[CH2:35][CH2:36][NH:31][C:32](=[O:37])[CH2:33]5)[CH:3]=[CH:4][CH:5]=4)=[N:9][N:10]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:11]3=[CH:12][N:13]=2)[CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 231360Piperazin-2-oneHCID 712540573-(6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712541544-(6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-2-oneYield 30.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

The mixture of 3-(6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine from Example 271 (211 mg, 0.5 mmol) and piperazin-2-one (100 mg, 1.0 mmol) in pyridine (5 mL) was heated at 130° C. for 16 h, and the reaction was monitored by LCMS. Upon completion of the reaction, the solvent was distilled off and the crude material was purified via flash chromatography, eluting with 5% to 30% acetate in heptane to afford 4-(6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-2-one as a yellow oil (76 mg, 30%). ESI MS m/z=501.23 (M+1).

Workup

  1. customUpon completion of the reaction
  2. distillationthe solvent was distilled off
  3. customthe crude material was purified via flash chromatography
  4. washeluting with 5% to 30% acetate in heptane

Sources & evidence

ORD record
ord-65062e21691c444d8caa23e1daeb4b1b
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260425B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes