N-Fluorobenzenesulfonimide → 4-(2,2-dimethylpropyl)-2-{fluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 216411노트

반응식

HRID 216411 반응식
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][C:12]([CH3:43])([CH2:41]C)[CH2:13][C:14]1[N:15]=[C:16]([C:25](=[O:40])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][N:34]=3)=[CH:29][CH:28]=2)[N:17]([S:19]([N:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH:18]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:54])(=O)=O)=CC=1>O1CCCC1>[CH3:11][C:12]([CH3:43])([CH3:41])[CH2:13][C:14]1[N:15]=[C:16]([C:25](=[O:40])[CH:26]([F:54])[C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][N:34]=3)=[CH:29][CH:28]=2)[N:17]([S:19]([N:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH:18]=1

참가 물질

5

반응물 3

HCID 588007N-FluorobenzenesulfonimideHCID 2733832Lithium HexamethyldisilazideHCID 667056774-(2,2-dimethylbutyl)-2-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

생성물 1

HCID 866385164-(2,2-dimethylpropyl)-2-{fluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

Lithium hexamethyldisilazide (1 M in tetrahydrofuran) (92 mL, 0.09 mmol) was added to a −78° C. solution of 4-(2,2-dimethylbutyl)-2-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (35 mg, 0.08 mmol) in tetrahydrofuran (2 mL). After stirring at −78° C. for 10 min, a solution of N-fluorobenzenesulfonimide (36 mg, 0.11 mmol) in tetrahydrofuran (1 mL) was added. The reaction was allowed to warm to ambient temperature, 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 0-50% ethyl acetate/hexane afforded 4-(2,2-dimethylpropyl)-2-{fluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

후처리

  1. temperatureto warm to ambient temperature
  2. customquenched 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-434711975a934e50bfeb7b264d9c10b9
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193228B2

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