Hydrochloric Acid → HCID 22336248, compound

HRID 1934359Notes

Reaction equation

HRID 1934359 reaction equation
[F:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl.[C:13](N)([CH3:16])([CH3:15])[CH3:14].CCN=C=NCCCN(C)C.Cl.C1C=CC2N([OH:39])N=NC=2C=1>O>[C:13]([NH:9][C:8]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:39])([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70604082-Cyano-3-fluoropyridine

Product 1

HCID 22336248HCID 22336248, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The extract was dried over Na2SO4 and the solvent was evaporated under a reduced pressure to give a mixture of regio-isomers of fluorocyanopyridine (0.9 g). Aqueous NaOH (4N, 10 ml) was added to the mixture of regio-isomers and heated under reflux for 2.5 hours. The mixture was allowed to cool, acidified with conc. hydrochloric acid and concentrated to dryness under a reduced pressure. The residue was suspended in DMF (10 ml), and t-butylamine (1.46 g, 20 mmol), WSC HCl (3.1 g, 16 mmol) and HOBt (2.2 g, 16 mmol) were added thereto and stirred overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous NaHCO3 and dried over Na2SO4. The solvent was evaporated under a reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1) to give the title compound (0.19 g; 12%).

Workup

  1. dry with materialThe extract was dried over Na2SO4
  2. customthe solvent was evaporated under a reduced pressure
  3. customto give
  4. temperatureheated
  5. temperatureunder reflux for 2.5 hours
  6. temperatureto cool
  7. concentrationconcentrated to dryness under a reduced pressure
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with saturated aqueous NaHCO3
  10. dry with materialdried over Na2SO4
  11. customThe solvent was evaporated under a reduced pressure
  12. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-39ee67d426f847579f26bb53ea2fef98
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Reaction notes

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