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

HRID 2204819Notes

Reaction equation

HRID 2204819 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>ClCCl>[NH2:1][C:2]1[C:3]([C:9](=[N:11][O:12][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:27])[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 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-amino-6-bromo-N′-hydroxypyrazine-2-carboximidamide (890 mg, 3.836 mmol) was suspended in dichloromethane (11.56 mL) and treated with triethylamine (427.0 mg, 588.2 μL, 4.220 mmol) followed by benzoyl chloride (593.2 mg, 489.8 μL, 4.220 mmol) The reaction mixture was allowed to stir for 1 hour and concentrated in vacuo. The resultant residue was triturated with methanol to give the desired product as a pale beige solid (891 mg, 69% Yield). 1H NMR (400.0 MHz, DMSO) d 7.55 (2H, m), 7.65 (1H, m), 7.90 (2H, br s), 8.28 (2H, m), 8.33 (1H, s); MS (ES+) 337.87

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was triturated with methanol

Sources & evidence

ORD record
ord-4f3584675e184326994f4a3d9b450eba
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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