tert-Butyl piperazine-1-carboxylate → 1,1-Dimethylethyl 4-[6-(acetylamino)-2-pyrazinyl]-1-piperazinecarboxylate

HRID 2182174Notes

Reaction equation

HRID 2182174 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[N:4][CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(O)C.C(OCC)(=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[N:7]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 14787673N-(6-chloropyrazin-2-yl)acetamide

Product 1

HCID 207821571,1-Dimethylethyl 4-[6-(acetylamino)-2-pyrazinyl]-1-piperazinecarboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(6-chloro-pyrazin-2-yl)-acetamide I-5a (58.6 mg, 0.34 mmol) and piperazine-1-carboxylic acid tert-butyl ester (636 mg, 3.42 mmol) in ethanol (2 mL) was stirred at reflux for 24 h. The reaction mixture was diluted with ethyl acetate (40 mL) and washed with 0.1M HCl (3×35 mL), brine, dried (Na2SO4), filtered, and evaporated to dryness. The crude residue was purified by preparative TLC using ethyl acetate as the eluant to afford the title compound I-5b (36.9 mg).

Workup

  1. temperatureat reflux for 24 h
  2. washwashed with 0.1M HCl (3×35 mL), brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude residue was purified by preparative TLC

Sources & evidence

ORD record
ord-3f7f94c9ee7b4a32af56eb1792b69306
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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