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 216417ノート

反応式

HRID 216417 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7139a5e741384d0588d9fce309b0ead5
出典データセット
uspto-grants-2012_06
特許番号
US08193228B2

反応ノート

読み込み中…