1-(4-Pyridyl)piperazine → HCID 54052804, compound

HRID 1782724Notes

Reaction equation

HRID 1782724 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([OH:20])=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[N:69]1[CH:74]=[CH:73][C:72]([N:75]2[CH2:80][CH2:79][NH:78][CH2:77][CH2:76]2)=[CH:71][CH:70]=1>CN(C=O)C>[CH3:25][C:24]([CH3:27])([O:23][C:21]([NH:1][C@H:2]([C:18]([N:78]1[CH2:79][CH2:80][N:75]([C:72]2[CH:73]=[CH:74][N:69]=[CH:70][CH:71]=2)[CH2:76][CH2:77]1)=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])=[O:22])[CH3:26]

Participants

7

Reactant 5

HCID 705171-(4-Pyridyl)piperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724765Boc-Lys(Z)-OHHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 54052804HCID 54052804, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 18.8 g (0.0494 mol) of Boc-Lys(Z)-OH, 6.5 g (0.05 mol) of DIEA, 16 g (0.05 mol) of TBTU, 6.6 g (0.049 mol) of HOBt and 100 ml of dimethylformamide were added dropwise, with stirring, 8.1 g (0.0494 mol) of 1-(4-pyridinyl)piperazine, dissolved in 40 ml of DMF, and the mixture was stirred over-night at room temperature. The solvent was removed in vacuo and the residue was taken up in ethyl acetate. The ethyl acetate phase was then washed three times successively with 70 ml of saturated aqueous sodium hydrogen carbonate solution and once with 70 ml of saturated aqueous saline solution, dried over sodium sulphate and evaporated down in vacuo. 24.2 g (93.2% of theory) of a yellowish oil were obtained, which was used for the following reactions without further purification.

Workup

  1. additionwere added dropwise
  2. stirringthe mixture was stirred over-night at room temperature
  3. customThe solvent was removed in vacuo
  4. washThe ethyl acetate phase was then washed three times successively with 70 ml of saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialonce with 70 ml of saturated aqueous saline solution, dried over sodium sulphate
  6. customevaporated down in vacuo
  7. custom24.2 g (93.2% of theory) of a yellowish oil were obtained
  8. customwhich was used for the following reactions without further purification

Sources & evidence

ORD record
ord-5eacc857d6964c20a82176fc7227bf45
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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