tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate

HRID 57807

Reaction equation

HRID 57807 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13](F)[N:12]=3)[C:4]=2[CH:3]=1.[C:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CS(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:12]=[C:13]([N:28]4[CH2:27][CH2:26][N:25]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:30][CH2:29]4)[CH:14]=[CH:15][CH:16]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 862802436-Chloro-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 86707015Tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylateYield 66.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 6-chloro-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine (100 mg, 0.40 mmol) and 1-N-Boc-piperazine (380 mg, 2.0 mmol) in dimethyl sulfoxide (3.0 mL) was heated at 95° C. 4 h. The reaction was quenched with water and 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 25% EtOAc) to give the desired product 110 mg 66% yield. MS (ESI) m/z: 415.1 [M+H]+

Workup

  1. custom4 h
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layers was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe crude product was purified by flash chromatography (EtOAc/Heptane 25% EtOAc)

Sources & evidence

ORD record
ord-f2929ce4b44b456db660d78e1984c5ad
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Linked notes

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