4-Aminopyridine → HCID 19082085, compound

HRID 963304Notes

Reaction equation

HRID 963304 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=2)=[N:7][CH:8]=1.S(Cl)(Cl)=O.[NH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>C1C=CC=CC=1.O.C(#N)C>[N:30]1[CH:31]=[CH:32][C:27]([NH:26][C:17](=[O:19])[CH2:16][C:13]2[CH:12]=[CH:11][C:10]([O:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:21])[F:20])=[CH:8][N:7]=3)=[CH:15][CH:14]=2)=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 19082076HCID 19082076, compound

Product 1

HCID 19082085HCID 19082085, compoundYield 11.9%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

3.0 g (10.1 mmol) of 4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetic acid was dissolved in 15 ml of benzene. Then, 1.8 g (15.1 mmol) of thionyl chloride was added thereto, and the mixture was refluxed under heating for 1.5 hours. Then, benzene and thionyl chloride were distilled off under reduced pressure. To the obtained residue, 15 ml of acetonitrile, 0.95 g (10.1 mmol) of 4-aminopyridine and 1.2 g (11.8 mmol) of triethylamine were added, and the mixture was refluxed under heating for 8 hours. After cooling, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.45 g of the desired product as a milky white powder (melting point: 167.0° to 170.0° C.).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1.5 hours
  3. distillationThen, benzene and thionyl chloride were distilled off under reduced pressure
  4. temperaturethe mixture was refluxed
  5. temperatureunder heating for 8 hours
  6. temperatureAfter cooling
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThen, ethyl acetate was distilled off under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e496c4b9f55a4644be229d8710ff8c73
Source dataset
uspto-grants-1998_06
Patent number
US05763463

Reaction notes

Loading…