Hydrochloric Acid → HCID 58336803, compound

HRID 2358983Notes

Reaction equation

HRID 2358983 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=C(C#N)C=CC=3)[CH:9]=[N:8]2)[CH:2]=1.[CH3:20][Mg]Cl.Cl.[C:24]([O-:36])(=O)[CH2:25][C:26]([CH2:31][C:32]([O-])=O)(C([O-])=O)O.[OH-].[Na+].[Na+].[Cl-]>C1COCC1.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:25]([C:24](=[O:36])[CH3:20])[CH:26]=[CH:31][CH:32]=3)[CH:9]=[N:8]2)[CH:2]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 31348CitrateHCID 51050006HCID 51050006, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 58336803HCID 58336803, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon, 0.52 g (2.1 mmol) of 6-(1-pyridin-3-yl-1H-pyrazol-4-yl)pyridine-2-carbonitrile in 100 ml of THF was stirred with 1.5 ml of methylmagnesium chloride (3 M, corresponds to 24 mmol) and a few spatula tips of CuBr-dimethyl sulphide complex at room temperature for 2 h. Dilute hydrochloric acid, citrate buffer and dil. aqueous sodium hydroxide solution to pH=9 and also aq. NaCl and ethyl acetate were added. The aqueous phase was extracted 3 times with ethyl acetate, and the combined organic phases were dried with MgSO4 and concentrated by evaporation. 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-0450db844f46441bbbc835431d767f08
Source dataset
uspto-grants-2014_04
Patent number
US08685964B2

Reaction notes

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