Piperazine → HCID 69732631, compound

HRID 2182158Notes

Reaction equation

HRID 2182158 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([C:16]1[CH:21]=[N:20][CH:19]=[C:18](Cl)[N:17]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CCO>[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)[C:16]1[N:17]=[C:18]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:19]=[N:20][CH:21]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 86588636HCID 86588636, compound

Product 1

HCID 69732631HCID 69732631, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (6-chloro-pyrazin-2-yl)-(3-fluoro-benzyl)-carbamic acid tert-butyl ester (1.14 g, 3.39 mmol) and piperazine (1.75 g, 20 mmol) in EtOH (34 mL) was stirred at reflux for 19 h. The reaction mixture was cooled and concentrated in vacuo. The residue was dissolved in Ethyl Acetate and washed with H2O (4×50 mL), brine, dried (Na2SO4), and concentrated to dryness. The crude product was chromatographed on Silica Gel (90 g) using 5% MeOH in CH2Cl2 as the eluant to give the title compound I-4c (1.09 g) as a pale yellow oil.

Workup

  1. temperatureat reflux for 19 h
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in Ethyl Acetate
  5. washwashed with H2O (4×50 mL), brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to dryness
  8. customThe crude product was chromatographed on Silica Gel (90 g)

Sources & evidence

ORD record
ord-a40a060b15404483bddfddc07fffb545
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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