Pyridine → 2-methoxy-5-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]pyridine

HRID 584737

반응식

HRID 584737 반응식
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=O)=[CH:11][N:10]=1.[F:18][C:19]([F:33])([F:32])[C:20](=[N:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[NH2:21].N1C=CC=CC=1>ClCCl.O1CCOCC1.CN(C)C=O>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]2[N:23]([C:24]3[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=3)[N:22]=[C:20]([C:19]([F:18])([F:32])[F:33])[N:21]=2)=[CH:11][N:10]=1

참가 물질

8

반응물 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 5924996-Methoxynicotinic acidHCID 696776222,2,2-trifluoro-N'-(4-methoxyphenyl)ethanehydrazonamide

생성물 1

HCID 99463822-methoxy-5-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]pyridine수율 14.9%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매2회

실험 절차

Under ice-cooling, oxalyl chloride (0.206 mL, 2.4 mmol) and then cat. dimethylformamide were added to a suspension of 6-methoxynicotinic acid (367 mg, 2.4 mmol) in 3 mL of dichloromethane. The mixture was stirred at room temperature for 1.5 hour. The solvent was removed under reduced pressure and the residue was azeotropped with dioxane. A solution of 2,2,2-trifluoro-N′-(4-methoxyphenyl)ethanehydrazonamide (466 mg, 2.0 mmol) and pyridine (0.194 mL, 2.4 mmol) in 5 mL of dioxane was added to a suspension of the residue in 1 mL of dioxane. The mixture was refluxed with stirring for 4 hours. After cooling, the solvent was removed under reduced pressure. The desired product was purified by silica gal column chromatogaraphy (hexane-ethyl acetate 4:1) to give 2-methoxy-5-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]pyridine (90 mg, 14.9% yield).

후처리

  1. temperatureUnder ice-cooling
  2. customThe solvent was removed under reduced pressure
  3. temperatureThe mixture was refluxed
  4. stirringwith stirring for 4 hours
  5. temperatureAfter cooling
  6. customthe solvent was removed under reduced pressure
  7. customThe desired product was purified by silica gal column chromatogaraphy (hexane-ethyl acetate 4:1)

출처 및 근거

ORD 기록
ord-500db38d9ed448bc8232cc8c8ade1e83
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927230B2

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