HCID 178513218, compound → HCID 22125572, compound

HRID 1858030Notes

Reaction equation

HRID 1858030 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[C:10]([C:24]([NH:26]O)=[NH:25])=[CH:11][C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[NH:14][C:13]=2[CH:23]=1>[Zn].C(O)(=O)C>[F:8][C:9]1[C:10]([C:24]([NH2:26])=[NH:25])=[CH:11][C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[NH:14][C:13]=2[CH:23]=1

Participants

4

Reactant 1

HCID 178513218HCID 178513218, compound

Product 1

HCID 22125572HCID 22125572, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture comprising 6-fluoro-N-hydroxy-2-pyridin-2-yl-1H-benzimidazole-5-carboxamidine trifluoroacetate (108 mg, 0.4 mmol), Zn (55 mg, 1.2 mmol) and acetic acid (5 mL) was heated at reflux under nitrogen for 2 hours. The mixture was filtered and concentrated to dryness. The residue was taken up and purified by preparative reverse phase HPLC. The combined pure fractions were lyophilized to provide 6-fluoro-2-pyridin-2-yl-1H-benzimidazole-5-carboxamidine; MS (ESI), Calculated for C13H10FN5 : 255.09, Found (MH+): 255.9; 1H-NMR (300 Mhz, DMSO-d6): 7.64-7.69 (m, 2H), 7.97 (d, 1H), 8.08 (m, 1H), 8.42 (d, 1H), 8.78 (d, 1H), 8.48 (d, 4H).

Workup

  1. temperatureat reflux under nitrogen for 2 hours
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated to dryness
  4. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-6171610637ab44fdb7fe2f4164439443
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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