1,1'-Carbonyldiimidazole → HCID 57893433, compound

HRID 1821650Notes

Reaction equation

HRID 1821650 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.N1([C:25](N2C=CN=C2)=[O:26])C=CN=C1>O1CCCC1>[Br:1][C:2]1[N:3]=[C:4]2[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)[C:25](=[O:26])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57893431HCID 57893431, compound

Product 1

HCID 57893433HCID 57893433, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-N3-(3-nitrobenzyl)pyrazine-2,3-diamine (100 mg, 0.31 mmol) in anhydrous tetrahydrofuran (10 mL) was added diimidazol-1-ylmethanone (250 mg, 1.51 mmol) at room temperature. After stirring overnight, the reaction was concentrated under reduced pressure. Purification of the resultant residue by flash chromatography [silica gel; hexanes/ethyl acetate (2:1)] afforded 6-bromo-1-(3- nitrobenzyl)-1,3-dihydroimidazo[4,5-b]pyrazin-2-one as a red-brown solid (95 mg, 88%).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. customPurification of the resultant residue by flash chromatography [silica gel; hexanes/ethyl acetate (2:1)]

Sources & evidence

ORD record
ord-d4445ac1278e4111b7d4d845ff349ae8
Source dataset
uspto-grants-2009_10
Patent number
US07608622B2

Reaction notes

Loading…