Oxalyl chloride → 5-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]2-methylpyridine

HRID 584726

반응식

HRID 584726 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[CH:4][N:3]=1.C(Cl)(=O)C(Cl)=O.[F:17][C:18]([F:32])([F:31])[C:19](=[N:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[NH2:20].C(N(C(C)C)CC)(C)C>ClCCl.O1CCOCC1.CN(C)C=O>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([N:22]2[C:6]([C:5]3[CH:9]=[CH:10][C:2]([CH3:1])=[N:3][CH:4]=3)=[N:20][C:19]([C:18]([F:17])([F:31])[F:32])=[N:21]2)=[CH:28][CH:27]=1

참가 물질

8

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 696776222,2,2-trifluoro-N'-(4-methoxyphenyl)ethanehydrazonamide

생성물 1

HCID 223415735-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]2-methylpyridine수율 15.3%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a suspension of 6-methylnicotinoic acid (329 mg, 2.4 mmol) in dichloromethane (3 mL), was added oxalyl chloride (0.209 mL, 2.4 mmol). And then 10 micro-L of dimethylformamide was added to the mixture. The mixture was stirred for 1 hour and the solvent was removed under reduced pressure. The residue was azeotroped with dichloromethane. To the residue, was added 3 mL of dioxane. Then a solution of 2,2,2-trifluoro-N′-(4-methoxyphenyl)ethanehydrazonamide (466 mg, 2 mmol) and diisopropylethylamine (0.418 mL, 2.4 mmol) in 4.5 mL of dioxane was added to the mixture and the mixture was refluxed with stirring for 3.5 hours. The solvent was removed under reduced pressure, and dichloromethane and 0.1 N hydrochloric acid were added to the residue. The organic layer was separated, washed with 0.1 N hydrochloric acid, water, and brine, dried over magnesium sulfate. The crude product was purified by silica gel column chromatography (8:1 toluene-ethyl acetate). The desired product was rinsed with hexane and dried in vacuo to give 5-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]2-methylpyridine (102 mg, 14.8% yield).

후처리

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was azeotroped with dichloromethane
  3. additionTo the residue, was added 3 mL of dioxane
  4. temperaturethe mixture was refluxed
  5. stirringwith stirring for 3.5 hours
  6. customThe solvent was removed under reduced pressure, and dichloromethane and 0.1 N hydrochloric acid
  7. additionwere added to the residue
  8. customThe organic layer was separated
  9. washwashed with 0.1 N hydrochloric acid, water, and brine
  10. dry with materialdried over magnesium sulfate
  11. customThe crude product was purified by silica gel column chromatography (8:1 toluene-ethyl acetate)
  12. washThe desired product was rinsed with hexane
  13. customdried in vacuo

출처 및 근거

ORD 기록
ord-ea8c156a96844c9a98f31272410485c5
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927230B2

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