1-Hydroxybenzotriazole → 2-(2-ethylsulfanyl-phenyl)-3-methyl-6-trifluoromethyl-3H-benzimidazole-4-ylamine

HRID 533647노트

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HRID 533647 반응식
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][C:4]=1[NH2:14].[CH2:15]([S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=O)[CH3:16].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>O.N1C=CC=CC=1>[CH2:15]([S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]1[N:2]([CH3:1])[C:3]2[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:11])([F:12])[F:13])=[CH:5][C:4]=2[N:14]=1)[CH3:16]

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68091212N'-methyl-5-trifluoromethyl-benzene-1,2,3-triamine

생성물 1

HCID 679816872-(2-ethylsulfanyl-phenyl)-3-methyl-6-trifluoromethyl-3H-benzimidazole-4-ylamine수율 15.2%

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

To a mixture of N′-methyl-5-trifluoromethyl-benzene-1,2,3-triamine (1.3 g), 2-ethylsulfanylbenzoic acid (1.3 g), and pyridine (12 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.4 g) and 1-hydroxybenzotriazole (86 mg) were added at room temperature. The mixture was stirred at room temperature for 5 hours, then heated to 110° C., and stirred with heating for 8 hours. After the reaction mixture was allowed to cool to room temperature, the reaction mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 339 mg of 2-(2-ethylsulfanyl-phenyl)-3-methyl-6-trifluoromethyl-3H-benzimidazole-4-ylamine (hereinafter, Present Compound 336).

후처리

  1. additionwere added at room temperature
  2. temperatureheated to 110° C.
  3. stirringstirred
  4. temperaturewith heating for 8 hours
  5. temperatureto cool to room temperature
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0cbd1663b2d84c7797cd713e2e24c962
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853238B2

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