Pyridine → 1-(4-methoxyphenyl)-5-[4-(1H-pyrrol-1yl)phenyl]-3-(trifluoro methyl)-1H-1,2,4-triazole

HRID 584736

反応式

HRID 584736 の反応式
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10](O)=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1.[F:27][C:28]([F:42])([F:41])[C:29](=[N:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[NH2:30]>ClCCl.O1CCOCC1.CN(C)C=O>[CH3:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([N:32]2[C:10]([C:9]3[CH:13]=[CH:14][C:6]([N:1]4[CH:5]=[CH:4][CH:3]=[CH:2]4)=[CH:7][CH:8]=3)=[N:30][C:29]([C:28]([F:27])([F:41])[F:42])=[N:31]2)=[CH:38][CH:37]=1

参加物

8

反応物 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 27372564-(1H-Pyrrol-1-yl)benzoic acidHCID 696776222,2,2-trifluoro-N'-(4-methoxyphenyl)ethanehydrazonamide

生成物 1

HCID 102000221-(4-methoxyphenyl)-5-[4-(1H-pyrrol-1yl)phenyl]-3-(trifluoro methyl)-1H-1,2,4-triazole収率 12.8%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

To a suspension of 4-(1H-pyrrol-1yl)benzoic acid (337 mg, 1.8 mmol) in dichloromethane (3.5 mL), oxalyl chloride (0.157 mL, 1.8 mmol) and then dimethylformamide (10 microL) were added. The mixture was stirred overnight. The solvent was removed under reduced pressure. Pyridine (0.146 mL, 1.8 mmol) and a solution of 2,2,2-trifluoro-N′-(4-methoxyphenyl)ethanehydrazonamide (350 mg, 1.5 mmol) in 3.5 mL of dioxane were added to a suspension of the acyl chloride in 3.5 mL of dioxane. The mixture was refluxed with stirring for 3 hours. After cooling, the solvent was removed under reduced pressure and 0.1 N hydrochloric acid and dichloromethane were added to the residue. The organic layer was separated and the aqueous layer was extracted with dichloromethane. A combined layer was washed with 0.1 N hydrochloric acid and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure. The desired product was purified by silica gel column chromatography (hexane-ethyl acetate 8:1-5:1) to give 1-(4-methoxyphenyl)-5-[4-(1H-pyrrol-1yl)phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole (74 mg, 12.8% yield)

後処理

  1. customThe solvent was removed under reduced pressure
  2. temperatureThe mixture was refluxed
  3. stirringwith stirring for 3 hours
  4. temperatureAfter cooling
  5. customthe solvent was removed under reduced pressure and 0.1 N hydrochloric acid and dichloromethane
  6. additionwere added to the residue
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with dichloromethane
  9. washA combined layer was washed with 0.1 N hydrochloric acid and brine
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was removed under reduced pressure
  12. customThe desired product was purified by silica gel column chromatography (hexane-ethyl acetate 8:1-5:1)

出典と根拠

ORDレコード
ord-486a064badbc40fb9bcfe0213c255bdc
出典データセット
uspto-grants-2005_08
特許番号
US06927230B2

関連ノート

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