Sodium Chloride → HCID 58336817, compound

HRID 2358981Notes

Reaction equation

HRID 2358981 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-88f1692c981c4c42b5f14ef5dc8aa00e
Source dataset
uspto-grants-2014_04
Patent number
US08685964B2

Reaction notes

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