Benzoyl chloride → 3-amino-N'-(benzoyloxy)-6-bromopyrazine-2-carboximidamide

HRID 78569Notes

Reaction equation

HRID 78569 reaction equation
[NH2:1][C:2]1[C:3]([C:9](=[N:11][OH:12])[NH2:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.C(N(CC)CC)C.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:9](=[N:11][O:12][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH2:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 136510283CID 136510283

Product 1

HCID 722951133-amino-N'-(benzoyloxy)-6-bromopyrazine-2-carboximidamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-amino-6-bromo-N′-hydroxypyrazine-2-carboximidamide (770 mg, 3.318 mmol) was suspended in DCM (10 mL) and triethylamine (369.3 mg, 508.7 μL, 3.650 mmol) followed by benzoyl chloride (513.1 mg, 423.7 μL, 3.650 mmol) were added. After 1 hour, the solvent was removed in vacuo and the residue triturated with MeOH. The resultant filtrate was filtered off to furnish the product as an off-white solid (779 mg, 70% Yield).

Workup

  1. additionwere added
  2. customthe solvent was removed in vacuo
  3. customthe residue triturated with MeOH
  4. filtrationThe resultant filtrate was filtered off

Sources & evidence

ORD record
ord-c4d68c66faac448696b203f14783cd85
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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