N-bromobutanimide → HCID 118049766, compound

HRID 595861Notes

Reaction equation

HRID 595861 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([C:9]2[N:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH2:4]1.C1C(=O)N([Br:23])C(=O)C1>C(#N)C>[Br:23][C:11]1[C:12]([NH2:15])=[N:13][CH:14]=[C:9]([C@@H:5]2[CH2:6][CH2:7][CH2:8][C@H:3]([O:2][CH3:1])[CH2:4]2)[N:10]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118049750HCID 118049750, compound

Product 1

HCID 118049766HCID 118049766, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

(+/−)-N,N-di-Boc-5-((1R,3S)-3-methoxycyclohexyl)pyrazin-2-amine (184 mg, 0.452 mmol) in DCM (4. 515 mL) was added HCl (4M in dioxane) (4.515 mL, 18.06 mmol). The reaction mixture was stirred at room temperature overnight. After the volatile material was removed in vacuo, the residue was dissolved in EtOAc. The organic layer was washed by NaHCO3 solution, water and brine, dried over anhydrous Na2SO4, and concentrated affording (+/−)-5-((1R,3S)-3-methoxycyclohexyl)pyrazin-2-amine in quantitative yield. LCMS (m/z): 208 (MH+), 0.43 min. To a solution of (+/−)-5-((1R,3S)-3-methoxycyclohexyl)pyrazin-2-amine (54 mg, 0.261 mmol) in acetonitrile (4. 008 μL) was added NBS (48.7 mg, 0.274 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 min. After quenched with NaHCO3, extracted with EtOAc three times. The organic layer was washed by water and brine, dried over anhydrous Na2SO4, and concentrated to afford 75 mg of (+/−)-3-bromo-5-((1R,3S)-3-methoxycyclohexyl)pyrazin-2-amine in quantitative yield. LCMS (m/z): 286 (MH+), 0.73 min.

Workup

  1. custom208 (MH+), 0.43 min
  2. customAfter quenched with NaHCO3
  3. extractionextracted with EtOAc three times
  4. washThe organic layer was washed by water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6755d065a2ef4fa78fa3fccd7b16db4c
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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