Hydrazine hydrate (1:1) → HCID 59570675, compound

HRID 1961722Notes

Reaction equation

HRID 1961722 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:13](Br)=[N:12][C:11]([Br:15])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].O.[NH2:18][NH2:19]>O1CCOCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:13]([NH:18][NH2:19])=[N:12][C:11]([Br:15])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59309651HCID 59309651, compound

Product 1

HCID 59570675HCID 59570675, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(3,5-Dibromo-pyrazin-2-yl)-carbamic acid tert-butyl ester (600 mg, 1.7 mmol) was dissolved in dioxane (10 mL) and cooled on an ice bath. Hydrazine monohydrate (3 mL, 61.7 mmol) was added and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and the remaining residue was re-dissolved in a mixture of ethylacetate, water and brine. The phases were separated and the aqeuous phase was extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with brine, dried over sodium sulphate, filtrated and concentrated in vacuo to give (5-bromo-3-hydrazino-pyrazin-2-yl)-carbamic acid tert-butyl ester as the crude product.

Workup

  1. temperaturecooled on an ice bath
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe remaining residue was re-dissolved in a mixture of ethylacetate, water and brine
  4. customThe phases were separated
  5. extractionthe aqeuous phase was extracted with ethyl acetate (3×30 mL)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltrated
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a592c429be534413bdaffaf7797bad6c
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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