Cesium carbonate → 1-(2-(6-(6-amino-pyridin-3-yloxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13358

反応式

HRID 13358 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-])=O)=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:17][C:18]1[C:19]([CH:41]2[CH2:45][CH2:44][CH2:43][N:42]2[C:46](=[O:48])[CH3:47])=[CH:20][C:21]2[N:25](COCC[Si](C)(C)C)[C:24]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)=[N:23][C:22]=2[CH:40]=1.[Cl-].[NH4+]>[Cu]=O.N1C=CC=CC=1>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([O:17][C:18]2[C:19]([CH:41]3[CH2:45][CH2:44][CH2:43][N:42]3[C:46](=[O:48])[CH3:47])=[CH:20][C:21]3[NH:25][C:24]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=4)=[N:23][C:22]=3[CH:40]=2)=[CH:3][CH:4]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 8176205-Bromo-2-nitropyridineHCID 231452771-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

生成物 1

HCID 231453671-(2-(6-(6-amino-pyridin-3-yloxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

試薬・触媒・溶媒 2

HCID 14829Copper oxide触媒HCID 1049Pyridine溶媒

反応条件

温度
120 °C

実験手順

53.5 mg of 5-bromo-2-nitro-pyridine, 84.2 mg of cesium carbonate and 25 mg of copper(II) oxide were added to a pyridine (1 ml) solution of 55.0 mg of 1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone obtained in Example 121 (step 10), and the reaction liquid was stirred overnight in a sealed tube at 120° C. After cooled, aqueous saturated ammonium chloride and saturated saline were added in order to the reaction liquid, extracted with ethyl acetate and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and 0.016 ml of hydrazine monohydrate and 20 mg of developed Raney nickel catalyst were added to an ethanol (2 ml) solution of the resulting residue, and the reaction liquid was stirred at room temperature for 30 minutes. The catalyst was removed through filtration through Celite, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1) to obtain the entitled compound as a yellow oily substance.

後処理

  1. customthe reaction liquid
  2. temperatureAfter cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure, and 0.016 ml of hydrazine monohydrate and 20 mg of developed Raney nickel catalyst
  6. additionwere added to an ethanol (2 ml) solution of the resulting residue
  7. customthe reaction liquid
  8. stirringwas stirred at room temperature for 30 minutes
  9. customThe catalyst was removed through filtration through Celite
  10. customthe solvent was evaporated away under reduced pressure
  11. customThe resulting residue was purified
  12. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1)
  13. customto obtain the entitled compound as a yellow oily substance

出典と根拠

ORDレコード
ord-50dad847ab5e448799a221a9eb97a01d
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

関連ノート

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