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tert-butyl N-[(3S)-piperidin-3-yl]carbamate → (S)-tert-butyl (1-(6-(6-(6-ethylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-yl)carbamate

HRID 57857
Notes
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Reaction equation

HRID 57857 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20](F)[N:19]=4)[C:11]=3[CH:10]=2)[CH:6]=[N:5][CH:4]=1)[CH3:2].[NH:25]1[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:26]1>CS(C)=O>[C:34]([O:33][C:32](=[O:38])[NH:31][C@H:27]1[CH2:28][CH2:29][CH2:30][N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([N:17]3[C:11]4[CH:10]=[C:9]([C:7]5[CH:6]=[N:5][CH:4]=[C:3]([CH2:1][CH3:2])[N:8]=5)[N:14]=[CH:13][C:12]=4[CH:15]=[N:16]3)[N:19]=2)[CH2:26]1)([CH3:37])([CH3:35])[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 867070546-(6-Ethylpyrazin-2-yl)-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine

Product 1

HCID 86707056(S)-tert-butyl (1-(6-(6-(6-ethylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-yl)carbamateYield 69.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A solution containing 6-(6-ethylpyrazin-2-yl)-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine (75 mg, 0.23 mmol) and tert-butyl N-[(3S)-3-piperidyl]carbamate (234 mg, 1.17 mmol) in methyl sulfoxide 2.0 mL was heated 95° C. The reaction was quenched with water then extracted with EtOAc. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 65% EtOAc) to give (S)-tert-butyl(1-(6-(6-(6-ethylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-yl)carbamate (80 mg) in 68% yield.

Workup

  1. customThe reaction was quenched with water
  2. extractionthen extracted with EtOAc
  3. dry with materialThe organic layers was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 65% EtOAc)

Sources & evidence

ORD record
ord-38545b2f4f1d488abaff1c72f5829b38
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434725B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes