Piperazine → HCID 66744445, compound

HRID 1959400Notes

Reaction equation

HRID 1959400 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[C:11]([N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:12][CH:13]=[C:14](Br)[N:15]=1.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CN(C=O)C.CCOC(C)=O.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[C:11]([N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:12][CH:13]=[C:14]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[N:15]=1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 86662082HCID 86662082, compound

Product 1

HCID 66744445HCID 66744445, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

Tert-butyl N-[3-(benzothiophen-2-yl)-5-bromo-pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (100 mg, 0.1975 mmol) was dissolved in DMF (781.2 μL) and treated with piperazine (170.1 mg, 1.975 mmol) and the reaction mixture heated at 100° C. for 30 minutes. The reaction was allowed to cool to ambient temperature and diluted with EtOAc/water and the layers separated. The organic layer was washed with water (3×), dried (MgSO4) and concentrated in vacuo. The material was used crude in the next step (92 mg, 91% Yield). 1H NMR (DMSO) d 1.23 (18H, s), 2.98 (4H, m), 3.59 (2H, m), 3.63 (2H, m), 7.29 (2H, m), 7.74 (3H, m), 7.89 (1H, s) ppm; MS (ES+) 511.98

Workup

  1. temperatureto cool to ambient temperature
  2. customthe layers separated
  3. washThe organic layer was washed with water (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a26120b25c746268abef6a939be19e9
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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