Pyridine → HCID 10132577, compound

HRID 584741Notes

Reaction equation

HRID 584741 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3](=[N:5][NH:6][C:7]1[CH:8]=[N:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)[NH2:4].[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=O)=[CH:21][CH:20]=1.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O1CCOCC1>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:23]([C:22]3[CH:26]=[CH:27][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)=[N:4][C:3]([C:2]([F:1])([F:15])[F:16])=[N:5]2)=[CH:8][N:9]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 69677616524699-83-0

Product 1

HCID 10132577HCID 10132577, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,2,2-trifluoro-N′-(6-methoxypyridin-3-yl)ethanehydrazonamide (0.2 g, 0.854 mmol), 4-methoxybenzoyl chloride (175 mg, 1.02 mmol), pyridine (0.083 mL, 1.02 mmol), and 4-dimethylaminopyridine (125 mg, 1.02 mmol) in dioxane (2 mL) was refluxed with stirring overnight. After cooling, the solvent was removed under reduced pressure. ethyl acetate-tetrahydrofuran (9:1) and water was poured into the residue and the organic layer was separated, washed with 0.1 N hydrochloric acid, water, and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography to give 2-methoxy-5-[5-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]pyridine (57 mg, 19.1% yield).

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. customthe solvent was removed under reduced pressure
  4. additionethyl acetate-tetrahydrofuran (9:1) and water was poured into the residue
  5. customthe organic layer was separated
  6. washwashed with 0.1 N hydrochloric acid, water, and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-300aeaed1eb14f0888bac19c4c2923bf
Source dataset
uspto-grants-2005_08
Patent number
US06927230B2

Reaction notes

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