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

HRID 216417노트

반응식

HRID 216417 반응식
C([Li])CCC.[CH3:6][C:7]([CH3:21])([CH3:20])[CH2:8][C:9]1[N:10]=[CH:11][N:12]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])[CH:13]=1.[F:22][C:23]([F:43])([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][N:37]=2)=[CH:32][CH:31]=1)[C:24](N(OC)C)=[O:25]>O1CCCC1>[F:43][C:23]([F:22])([C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][N:37]=2)=[CH:34][CH:35]=1)[C:24]([C:11]1[N:12]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])[CH:13]=[C:9]([CH2:8][C:7]([CH3:21])([CH3:20])[CH3:6])[N:10]=1)=[O:25]

참가 물질

5

반응물 3

HCID 591403964-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamideHCID 866385172,2-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-N-methoxy-N-methylacetamideHCID 178418339Butyllithium

생성물 1

HCID 686681282-{difluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

n-Butyllithium (1.6 M in hexane) (0.60 mL, 0.96 mmol) was added to a −78° C. solution of 4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (234 mg, 0.96 mmol) in tetrahydrofuran (10 mL). After stirring at −78° C. for 10 min, 2,2-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-N-methoxy-N-methylacetamide (296 mg, 0.96 mmol) was added and the reaction 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 2-{difluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-4-(2,2-dimethylpropyl)-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-7139a5e741384d0588d9fce309b0ead5
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193228B2

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