N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide → 2-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide

HRID 425370노트

반응식

HRID 425370 반응식
C([Li])CCC.[CH3:6][N:7]([CH3:25])[S:8]([N:11]1[CH:15]=[C:14]([CH2:16][C:17]([CH3:24])([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH2:19])[N:13]=[CH:12]1)(=[O:10])=[O:9].[F:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][C:40](OC)=[O:41])=[CH:35][CH:34]=2)=[N:31][CH:32]=1>O1CCCC1>[F:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][C:40]([C:12]3[N:11]([S:8]([N:7]([CH3:6])[CH3:25])(=[O:10])=[O:9])[CH:15]=[C:14]([CH2:16][C:17]([CH3:24])([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH2:19])[N:13]=3)=[O:41])=[CH:35][CH:34]=2)=[N:31][CH:32]=1

참가 물질

5

반응물 3

HCID 59140382N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide2회HCID 86637794Methyl [4-(5-fluoropyridin-2-yl)phenyl]acetateHCID 178418339Butyllithium

생성물 1

HCID 667055982-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

n-Butyllithium (1.6 M in hexane) (4.19 mL, 6.7 mmol) was added to a −78° C. solution of N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide (Intermediate 4) (1.74 g, 5.59 mmol) in tetrahydrofuran (6 mL). After warming to −10° C. over 1 h, methyl [4-(5-fluoropyridin-2-yl)phenyl]acetate (1.14 g, 5.59 mmol) in tetrahydrofuran (6 mL) was added and the reaction allowed to warm to ambient temperature. After stirring at ambient temperature for 3 h, the reaction mixture was quenched with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded 2>{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide.

후처리

  1. temperatureto warm to ambient temperature
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with methylene chloride and ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-209afb550a8c4a50a998e2636993ce28
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106070B2

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