N-bromobutanimide → HCID 16070450, compound

HRID 1710711Notes

Reaction equation

HRID 1710711 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:11]=[C:10]([NH2:12])[CH:9]=[N:8][C:7]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[Br:19]N1C(=O)CCC1=O>CS(C)=O.O>[Br:19][C:9]1[C:10]([NH2:12])=[N:11][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[C:7]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:8]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 59457582HCID 59457582, compound

Product 1

HCID 16070450HCID 16070450, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a 0° C. stirred solution of 6-(2-furyl)-5-pyridin-4-ylpyrazin-2-amine (Example 5, 195 mg, 0.82 mmol) in dimethylsulfoxide (1.5 mL) and water (40 μL), was added portionwise N-bromosuccinimide (146 mg, 0.82 mmol). The mixture was stirred at room temperature for 40 min, then poured into water, extracted with dichloromethane (×3), the organic layers washed with brine, dried (MgSO4) and evaporated to furnish the title compound (198 mg, 75%) as a brown solid.

Workup

  1. extractionextracted with dichloromethane (×3)
  2. washthe organic layers washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-83f4f788cbfd4fd2a6b3dde6d3615478
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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