Cyanogen Bromide → HCID 136354821, compound

HRID 2249524Notes

Reaction equation

HRID 2249524 reaction equation
C[O:2][C:3]([C:5]1[N:6](S(C)(=O)=O)[CH:7]=[C:8]([C:10](=[N:20][NH2:21])[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])[CH:9]=1)=[O:4].Br[C:27]#[N:28]>CO>[NH2:28][C:27]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])[C:10]([C:8]2[CH:9]=[C:5]([C:3]([OH:2])=[O:4])[NH:6][CH:7]=2)=[N:20][N:21]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 178498203HCID 178498203, compound

Product 1

HCID 136354821HCID 136354821, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[N-(2,3-dichloro-phenyl)-N′-amino-carbamimidoyl]-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid methyl ester (Prepared by the same method described above for the preparation of the corresponding difluoro compound) (150 mg, 0.37 mmol) in MeOH (2 mL) was added BrCN (60 mg, 0.57 mmol) at RT. The mixture was stirred at RT for 12 h. The solvent was removed by evaporation, the residue was dissolved in MeOH (4 mL), and the resulting solution was treated with 6N NaOH (1 mL) at 50° C. for 4 h. After cooling to RT, the solution was acidified with 6N HCl. The organic solvent was evaporated, the remaining aqueous solution was diluted with CH3CN, and the inorganic salt was removed by filtration. The filtrate was concentrated under vacuum to give a crude product, which was purified by HPLC for next reaction. MS (ES+): m/e=338.0 (M+H); LC: 2.44 min.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in MeOH (4 mL)
  3. additionthe resulting solution was treated with 6N NaOH (1 mL) at 50° C. for 4 h
  4. temperatureAfter cooling to RT
  5. customThe organic solvent was evaporated
  6. additionthe remaining aqueous solution was diluted with CH3CN
  7. customthe inorganic salt was removed by filtration
  8. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-9285d3df15b241f1ae51300b244ac3b9
Source dataset
uspto-grants-2008_01
Patent number
US07314885B2

Reaction notes

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