1-(4-Pyridyl)piperazine → HCID 11591778, compound

HRID 1782725Notes

Reaction equation

HRID 1782725 reaction equation
[NH:1]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:2]([C:15]([OH:17])=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[N:60]1[CH:65]=[CH:64][C:63]([N:66]2[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]2)=[CH:62][CH:61]=1.CCN(C(C)C)C(C)C>CN(C)C=O>[C:22]1([CH2:21][O:20][C:18]([NH:1][C@H:2]([C:15]([N:69]2[CH2:70][CH2:71][N:66]([C:63]3[CH:64]=[CH:65][N:60]=[CH:61][CH:62]=3)[CH2:67][CH2:68]2)=[O:17])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])=[O:19])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 705171-(4-Pyridyl)piperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 98765IN2-(benzyloxycarbonyl)-N6-(tert-butoxycarbonyl)-L-lysineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 11591778HCID 11591778, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 100 g (0.263 mol) of Z-Lys(Boc)-OH, 86.1 g (0.268 mol) of TBTU and 36.3 g (0.263 mol) of HOBt in 600 ml of dimethylformamide were added 43.0 g (0.263 mol) of 1-(4-pyridinyl)-piperazine and 47.2 ml (0.268 mol) of DIEA with stirring and the mixture was stirred overnight at room temperature. The reaction mixture was evaporated down in vacuo and the residue divided between ethyl acetate and aqueous saturated sodium hydrogen carbonate solution. The aqueous phase was extracted twice more with a mixture of ethyl acetate/methanol (10/1, v/v) and the combined organic phases were washed once with saturated sodium hydrogen carbonate solution. The organic phase was, after drying over sodium sulphate, evaporated down in vacuo and the residue was taken up in 750 ml of ethyl acetate and washed four times with 100 ml of water, six times with 100 ml of 1% potassium hydrogen sulphate solution, once with 100 ml of water, twice with 100 ml of 3% aqueous ammonia solution and twice with 100 ml of water. The organic phase was evaporated down after drying over sodium sulphate. 120 g (87% of theory) of the desired product were obtained as an oil, which was used without further purification for the subsequent reactions.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe reaction mixture was evaporated down in vacuo
  3. extractionThe aqueous phase was extracted twice more with a mixture of ethyl acetate/methanol (10/1
  4. washv/v) and the combined organic phases were washed once with saturated sodium hydrogen carbonate solution
  5. dry with materialafter drying over sodium sulphate
  6. customevaporated down in vacuo
  7. washwashed four times with 100 ml of water, six times with 100 ml of 1% potassium hydrogen sulphate solution
  8. customThe organic phase was evaporated down
  9. dry with materialafter drying over sodium sulphate

Sources & evidence

ORD record
ord-000db519bd8e41afb6aaf1c6eb285b2e
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

Loading…