Benzoyl chloride → HCID 178513420, compound

HRID 78596Notes

Reaction equation

HRID 78596 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](=[NH:10])[NH:11][O:12][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:27])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 136510283CID 136510283

Product 1

HCID 178513420HCID 178513420, compoundYield 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-2b74395f6c454a64b8d47c3fbcd260f1
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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