HCID 178468754, compound → HCID 178511945, compound

HRID 1858025Notes

Reaction equation

HRID 1858025 reaction equation
[C:1]([C:4]1[CH:23]=[CH:22][C:7]2[NH:8][C:9]([C:11]3[N:16]=[CH:15][C:14]([C:17]([O:19]CC)=[O:18])=[CH:13][CH:12]=3)=[N:10][C:6]=2[CH:5]=1)(=[NH:3])[NH2:2]>Cl>[C:1]([C:4]1[CH:23]=[CH:22][C:7]2[NH:8][C:9]([C:11]3[N:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=3)=[N:10][C:6]=2[CH:5]=1)(=[NH:2])[NH2:3]

Participants

3

Reactant 1

HCID 178468754HCID 178468754, compound

Product 1

HCID 178511945HCID 178511945, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture comprising ethyl 6-(5-amidino-1H-benzimidazol-2-yl)pyridine-3-carboxylate (1.7 g, 5.7 mmol) and 3N hydrochloric acid (60 mL) was heated at reflux for 24 hours. The mixture was cooled, concentrated to one quarter volume and poured into stirring acetonitrile (200 mL) to give a precipitate. The precipitate was filtered and dried under vacuum to provide 6-(5-amidino-1H-benzimidazol-2-yl)pyridine-3-carboxylic acid (1.4 g, 5.0 mmol). 1H-NMR (300 Mhz, DMSO-d6): 7.7 (m, 2H), 8.2 (s, 1H), 8.5 (m, 2H), 9.2 (s, 1H), 9.3 (s, 2H) 9.5 (s, 2H); MS (ESI), Calculated for C14H11N5O2 : 281.3, Found (MH+): 281.9.

Workup

  1. temperatureat reflux for 24 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated to one quarter volume
  4. additionpoured
  5. customto give a precipitate
  6. filtrationThe precipitate was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-382f91d8779b44b3ae4a552451b83f8d
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

Loading…