Sodium Chloride → HCID 58336817, compound

HRID 2176410Notes

Reaction equation

HRID 2176410 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:12]=[N:13][N:14]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:15]=2)[N:6]=1)=[NH:4].[C:22](OCC)(=O)C.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[Na+].[Cl-]>C1COCC1.C(OCC)(OCC)OCC>[O:1]1[CH:22]=[N:4][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]3[CH:12]=[N:13][N:14]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[CH:15]=3)[N:6]=2)=[N:2]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 31348CitrateHCID 178513286HCID 178513286, compound

Product 1

HCID 58336817HCID 58336817, compound

Reagents, catalysts & solvents 1

HCID 70381227HCID 70381227, compoundSolvent

Procedure

0.24 g of N-hydroxy-6-(1-pyridin-3-yl-1H-pyrazol-4-yl)pyridine-2-carboxamidine (crude product from the previous step) was dissolved in THF/triethyl orthoformate, and 0.2 g of BF3-ET2O was added. After 2 h, ethyl acetate, aq. citrate buffer pH=6 and aq. NaCl were added and the aqueous phase was extracted 3 times with ethyl acetate. The combined organic phases were dried with MgSO4 and concentrated by evaporation, and the residue was purified by chromatography on silica gel (petroleum ether/acetone).

Workup

  1. extractionthe aqueous phase was extracted 3 times with ethyl acetate
  2. dry with materialThe combined organic phases were dried with MgSO4
  3. concentrationconcentrated by evaporation
  4. customthe residue was purified by chromatography on silica gel (petroleum ether/acetone)

Sources & evidence

ORD record
ord-da1cc0319fbc49bd8bcec2dfbb08e87d
Source dataset
uspto-grants-2015_06
Patent number
US09066518B2

Reaction notes

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