Ethyl Acetate → 5-(4-Boc-piperazin-1-yl)-3-chloro[1,2,4]triazine

HRID 490099Notes

Reaction equation

HRID 490099 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6](Cl)[N:7]=1.C(N(C(C)C)CC)(C)C.[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].C(OCC)(=O)C>O1CCOCC1>[C:18]([N:25]1[CH2:26][CH2:27][N:28]([C:6]2[N:7]=[C:2]([Cl:1])[N:3]=[N:4][CH:5]=2)[CH2:29][CH2:30]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 122649333,5-Dichloro-1,2,4-triazine

Product 1

HCID 576741865-(4-Boc-piperazin-1-yl)-3-chloro[1,2,4]triazineYield 31.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3,5-dichloro[1,2,4]triazine (0.34 g, 2.28 mmol.) in anhydrous dioxane (4 mL) was add diisopropylethylamine (0.44 g, 3.41 mmol.) and N—Boc-piperazine (0.424 g, 2.28 mmol.). The reaction mixture was stirred at room temperature for 40 minutes. Ethyl acetate (200 mL) was added. The organic solution was washed with saturated ammonium chloride solution, water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporation under reduced pressure. The crude product was purified by RP-HPLC to yield the desired 5-(4-Boc-piperazin-1-yl)-3-chloro[1,2,4]triazine 151 (0.212 g, 0.71 mmol.).

Workup

  1. washThe organic solution was washed with saturated ammonium chloride solution, water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporation under reduced pressure
  4. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-b9250beff4904051a0e31e6027b56d63
Source dataset
uspto-grants-2009_05
Patent number
US07528132B2

Reaction notes

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