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1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → 1-(2-(2-amino-5-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-tetrazol-5-yl)pyridin-3-yl)benzo[b]thiophen-5-yl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea

HRID 2199622
ノート
印刷プレビュー

反応式

HRID 2199622 の反応式
[NH2:1][C:2]1[CH:33]=[CH:32][C:5]2[S:6][C:7]([C:9]3[C:10]([NH2:31])=[N:11][CH:12]=[C:13]([C:15]4[N:19]([CH2:20][CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[N:18]=[N:17][N:16]=4)[CH:14]=3)=[CH:8][C:4]=2[CH:3]=1.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([N:41]=[C:42]=[O:43])=[CH:37][C:36]=1[C:44]([F:47])([F:46])[F:45]>O1CCCC1.C(OCC)(=O)C>[NH2:31][C:10]1[C:9]([C:7]2[S:6][C:5]3[CH:32]=[CH:33][C:2]([NH:1][C:42]([NH:41][C:38]4[CH:39]=[CH:40][C:35]([Cl:34])=[C:36]([C:44]([F:46])([F:45])[F:47])[CH:37]=4)=[O:43])=[CH:3][C:4]=3[CH:8]=2)=[CH:14][C:13]([C:15]2[N:19]([CH2:20][CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:25])[CH3:26])[N:18]=[N:17][N:16]=2)=[CH:12][N:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 1317356943-(5-aminobenzo[b]thiophen-2-yl)-5-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-tetrazol-5-yl)pyridin-2-amine

生成物 1

HCID 1317356961-(2-(2-amino-5-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-tetrazol-5-yl)pyridin-3-yl)benzo[b]thiophen-5-yl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To the stirring solution of 3-(5-aminobenzo[b]thiophen-2-yl)-5-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-tetrazol-5-yl)pyridin-2-amine (123 mg, 0.256 mmol, 1 eq) in anhydrous tetrahydrofuran (3 mL) under nitrogen atmosphere was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (58 mg, 1 eq) and the reaction mixture was stirred at room temperature for three hours. The reaction was then diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine, and dried with anhydrous sodium sulfate. The upper clear solution was decanted and concentrated under reduced pressure and loaded onto silica. The mixture was subject to a gradient column chromatography (EtOAc-Hex 1:5 to 2:1) to give 1-(2-(2-amino-5-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-tetrazol-5-yl)pyridin-3-yl)benzo[b]thiophen-5-yl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea as a white solid in the amount of 130 mg.

後処理

  1. washwashed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe upper clear solution was decanted
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d694df39eed646ae9bdde48387d17bd0
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09359336B2

反応ノート

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