Potassium Carbonate → 4-(3-Pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 221371Notes

Reaction equation

HRID 221371 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]=[C:10]([CH2:12]OS(C)(=O)=O)[O:9][N:8]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>C(#N)C>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][N:34]([CH2:12][C:10]2[O:9][N:8]=[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[N:11]=2)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 57954388Methanesulfonic acid 3-pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl ester

Product 1

HCID 521264924-(3-Pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methanesulfonic acid 3-pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl ester (Preparation 12, 56 mg, 0.22 mmol) and potassium carbonate (30 mg, 0.22 mmol) were added to a solution of piperazine-1-carboxylic acid tert-butyl ester (37 mg, 0.2 mmol) in acetonitrile (4 ml). The stirred mixture was heated under reflux for 18 h, the solvent removed and the residue dissolved in EtOAc-water (90:10, 50 ml). The organic phase was separated, washed with brine, dried (MgSO4) and the solvent removed to give a residue which was purified by flash chromatography (IH-EtOAc, 4:1), affording the title compound: RT=3.26 min; m/z (ES+)=346.1 [M+H]+.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 18 h
  3. customthe solvent removed
  4. dissolutionthe residue dissolved in EtOAc-water (90:10, 50 ml)
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed
  9. customto give a residue which
  10. customwas purified by flash chromatography (IH-EtOAc, 4:1)

Sources & evidence

ORD record
ord-d9d78052339349f3b8cb1699a9f53323
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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