Cesium carbonate → 6-((2R,5S)-1-acetyl-5-methylpyrrolidin-2-yl)-5-(4-methanesulfonyl-phenoxy)-2-pyrazin-2-yl-1H-benzimidazole

HRID 13424ノート

反応式

HRID 13424 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].[C:18]([N:21]1[C@@H:25]([CH3:26])[CH2:24][CH2:23][C@@H:22]1[C:27]1[C:32](F)=[CH:31][C:30]([NH:34][C:35]([C:37]2[CH:42]=[N:41][CH:40]=[CH:39][N:38]=2)=O)=[C:29]([N+:43]([O-])=O)[CH:28]=1)(=[O:20])[CH3:19].O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CN1CCCC1=O>[C:18]([N:21]1[C@@H:25]([CH3:26])[CH2:24][CH2:23][C@@H:22]1[C:27]1[C:32]([O:11][C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[CH:31][C:30]2[N:34]=[C:35]([C:37]3[CH:42]=[N:41][CH:40]=[CH:39][N:38]=3)[NH:43][C:29]=2[CH:28]=1)(=[O:20])[CH3:19]

参加物

8

反応物 5

HCID 10796Cesium carbonateHCID 61436Stannous chloride dihydrateHCID 1233504-(Methylsulfonyl)phenolHCID 516892Sodium BicarbonateHCID 67482980N-(4-((2R,5S)-1-acetyl-5-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyrazine-2-carboxamide

生成物 1

HCID 674824346-((2R,5S)-1-acetyl-5-methylpyrrolidin-2-yl)-5-(4-methanesulfonyl-phenoxy)-2-pyrazin-2-yl-1H-benzimidazole

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
90 °C

実験手順

9.2 mg of 4-methanesulfonyl-phenol and 26.2 mg of cesium carbonate were added to an N-methylpyrrolidinone (1 ml) solution of 10.4 mg of N-(4-((2R,5S)-1-acetyl-5-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyrazine-2-carboxamide, and the reaction liquid was stirred at 90° C. for 1 hour. 60 mg of tin(II) chloride dihydrate was added to it, and the reaction liquid was stirred at 90° C. for 1 h our and at 100° C. for 2 hours. Ethyl acetate and aqueous saturated sodium bicarbonate were added to the reaction liquid, the resulting deposit was removed through filtration, extracted with ethyl acetate, and the organic layer was washed with water and saturated saline, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a pale yellow oily substance.

後処理

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred at 90° C. for 1 h our
  4. waitat 100° C. for 2 hours
  5. customthe resulting deposit was removed through filtration
  6. extractionextracted with ethyl acetate
  7. washthe organic layer was washed with water and saturated saline
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customThe solvent was evaporated away under reduced pressure
  10. custompurified
  11. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)
  12. customto obtain the entitled compound as a pale yellow oily substance

出典と根拠

ORDレコード
ord-d265047972684777bbca1568e1cf2fb9
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

反応ノート

読み込み中…