N-bromobutanimide → HCID 118045542, compound

HRID 595871Notes

Reaction equation

HRID 595871 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[N:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C1C(=O)N([Br:25])C(=O)C1>C(#N)C>[Br:25][C:13]1[C:14]([NH2:17])=[N:15][CH:16]=[C:11]([CH:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)[N:12]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118046609HCID 118046609, compound

Product 1

HCID 118045542HCID 118045542, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazin-2-amine (620 mg, 2.64 mmol) was added Acetonitrile (20 mL) and then was added NBS (469 mg, 2.64 mmol) in portions over 2 min. The reaction was stirred at room temperature for 20 min and quenched with saturated sodium bicarbonate solution, and 250 mL of ethyl acetate was added. The aqueous was extracted and the organic layer was washed with saturated sodium bicarbonate, water (2×), saturated salt solution, then dried with sodium sulfate, filtered and concentrated to residue to give 650 mg of the desired product, used as is, (79% yield). LCMS (m/z): 314.1/316.1 (MH+), 0.61 min.

Workup

  1. customquenched with saturated sodium bicarbonate solution, and 250 mL of ethyl acetate
  2. additionwas added
  3. extractionThe aqueous was extracted
  4. washthe organic layer was washed with saturated sodium bicarbonate, water (2×), saturated salt solution
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to residue

Sources & evidence

ORD record
ord-1cd414cc9dd246ac8a171f0c8b04a9ee
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

Loading…