Cesium carbonate → 6-(1-acetyl-4-methylpyrrolidin-2-yl)-5-(4-(methanesulfonyl)phenoxy)-2-pyridin-2-yl-1H-benzimidazole

HRID 13428

反応式

HRID 13428 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[CH2:25][CH:24]([CH3:26])[CH2:23][CH:22]1[C:27]1[C:32](F)=[CH:31][C:30]([NH:34][C:35]([C:37]2[CH:42]=[CH: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)(Cl)Cl>C(OCC)(=O)C.CN1CCCC1=O>[C:18]([N:21]1[CH2:25][CH:24]([CH3:26])[CH2:23][CH: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]=[CH:41][CH:40]=[CH:39][N:38]=3)[NH:43][C:29]=2[CH:28]=1)(=[O:20])[CH3:19]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 1233504-(Methylsulfonyl)phenolHCID 23145536N-(4-(1-acetyl-4-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyridine-2-carboxamideHCID 85782573Tin tetrachloride dihydrate

生成物 1

HCID 231452966-(1-acetyl-4-methylpyrrolidin-2-yl)-5-(4-(methanesulfonyl)phenoxy)-2-pyridin-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

13.4 mg of 4-(methanesulfonyl)phenol and 44.9 mg of cesium carbonate were added in order to an N-methyl-pyrrolidinone (2 ml) solution of 15 mg of N-(4-(1-acetyl-4-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyridine-2-carboxamide, and the reaction liquid was stirred at 90° C. for 1 hour. 43.8 mg of tin chloride dihydrate was added to the reaction liquid, then heated up to 100° C. and stirred for 2 hours. The reaction liquid was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 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 white solid.

後処理

  1. customthe reaction liquid
  2. temperatureheated up to 100° C.
  3. stirringstirred for 2 hours
  4. customThe reaction liquid
  5. washwashed with aqueous saturated sodium bicarbonate
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified
  9. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1)

出典と根拠

ORDレコード
ord-19d0527dd4c44853b78367b7e8838554
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

関連ノート

読み込み中…