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Acetonitrile → N-(2-(3-benzyl-6-fluoro-2-(3-methylazetidin-1-yl)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 587886
ノート
印刷プレビュー

反応式

HRID 587886 の反応式
[NH2:1][CH:2]1[CH:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([F:31])=[C:7]([O:18][CH2:19][CH2:20][NH:21][S:22]([C:25]3[N:26]=[CH:27][N:28]([CH3:30])[CH:29]=3)(=[O:24])=[O:23])[CH:8]=2)[CH2:3]1.Br[CH2:33][CH:34]([CH3:37])[CH2:35]Cl.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O.ClCCl>[CH2:11]([CH:10]1[C:9]2[C:4](=[CH:5][C:6]([F:31])=[C:7]([O:18][CH2:19][CH2:20][NH:21][S:22]([C:25]3[N:26]=[CH:27][N:28]([CH3:30])[CH:29]=3)(=[O:24])=[O:23])[CH:8]=2)[CH2:3][CH:2]1[N:1]1[CH2:35][CH:34]([CH3:37])[CH2:33]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 955661-Bromo-3-chloro-2-methylpropaneHCID 66740582N-(2-(2-amino-3-benzyl-6-fluoro-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

生成物 1

HCID 56837079N-(2-(3-benzyl-6-fluoro-2-(3-methylazetidin-1-yl)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

試薬・触媒・溶媒

2
HCID 962Water触媒HCID 6344Dichloromethane溶媒

実験手順

To N-(2-(2-amino-3-benzyl-6-fluoro-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide (20.7 mg, 0.047 mmol), 10 equivalents 1-bromo-3-chloro-2-methylpropane and potassium carbonate (70.8 mg) in water (1 mL)+1 drop acetonitrile were added. Microwave at 120° C. Evaporated acetonitrile, re-dissolved in dichloromethane and extracted with water and brine, dried over sodium bicarbonate, filtered and evaporated to obtain the crude product and was purified by flash silica gel chromatography on 4 g SiO2-cartridge using 10% methanol in dichloromethane to afford N-(2-(3-benzyl-6-fluoro-2-(3-methylazetidin-1-yl)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide as a clear glass m=2.0 mg (8.6%)

後処理

  1. customat 120° C
  2. extractionextracted with water and brine
  3. dry with materialdried over sodium bicarbonate
  4. filtrationfiltered
  5. customevaporated
  6. customto obtain the crude product
  7. customwas purified by flash silica gel chromatography on 4 g SiO2-cartridge

出典と根拠

ORDレコード
ord-d133f7aec27049d99fdc6305b836533a
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09227930B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート