Piperazine → HCID 66744546, compound

HRID 1959383Notes

Reaction equation

HRID 1959383 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]#[C:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[N:20][C:19](Br)=[CH:18][N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>CN(C=O)C.CCOC(C)=O.O>[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]#[C:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[N:20][C:19]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:18][N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 4837PiperazineHCID 58070279Tert-butyl N-tert-butoxycarbonyl-N-[5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl]carbamate

Product 1

HCID 66744546HCID 66744546, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

Tert-butyl N-tert-butoxycarbonyl-N-[5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl]carbamate (640 mg, 1.360 mmol) was dissolved in DMF (5 mL) and treated with piperazine (351.4 mg, 4.080 mmol). The reaction was allowed to heat at 100° C. for 15 minutes and then allowed to cool to ambient temperature and diluted with EtOAc/water. The aqueous layer was extracted with EtOAc and the combined organics washed with water (2×) and brine (2×). This was dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petrol to 10% MeOH/DCM/1% NH4OH) to afford the title compound as a yellow oil (494 mg, 76% Yield). 1H NMR (400.0 MHz, DMSO) d 0.03 (s, 9H), 1.18 (s, 18H), 2.99 (m, 4H), 3.29 (m, 4H) and 7.88 (s, 1H) ppm; MS (ES+) 476.08

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organics washed with water (2×) and brine (2×)
  4. dry with materialThis was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petrol to 10% MeOH/DCM/1% NH4OH)

Sources & evidence

ORD record
ord-25145c5cd0314c0384d618705ac41066
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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