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Ethanol → 2-(2,2-Dimethylpropyl)-5-(isopropylsulfonyl)-1-(2-pyrrolidin-1-ylethyl)-1H-benzimidazole

HRID 1817856
ノート
印刷プレビュー

反応式

HRID 1817856 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[C:22]([CH2:26][C:27](Cl)=O)([CH3:25])([CH3:24])[CH3:23].[OH-].[Na+].C(O)C>C(OCC)(=O)C>[CH3:23][C:22]([CH3:25])([CH3:24])[CH2:26][C:27]1[N:14]([CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:3]2[CH:4]=[CH:5][C:6]([S:8]([CH:11]([CH3:12])[CH3:13])(=[O:9])=[O:10])=[CH:7][C:2]=2[N:1]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 815143,3-Dimethylbutanoyl chlorideHCID 688708672-Amino-4-(isopropylsulfonyl)-1-(N-2-pyrrolidine-1-ylethylamino)benzene

生成物 1

HCID 115456142-(2,2-Dimethylpropyl)-5-(isopropylsulfonyl)-1-(2-pyrrolidin-1-ylethyl)-1H-benzimidazole収率 70.7%

試薬・触媒・溶媒 1

HCID 8857
Ethyl Acetate
溶媒

実験手順

To a solution of 2-amino-4-(isopropylsulfonyl)-1-(N-2-pyrrolidine-1-ylethylamino)benzene (122.9 mg, 0.39 mmol) in ethyl acetate (8 mL) was added tert-butylacetyl chloride (60 μL, 0.43 mmol) at room temperature, and the mixture was stirred for 1 h at room temperature. 2N—NaOH (1 mL) and ethanol (3 mL) were then added to the reaction mixture at room temperature, and stirred for 6 h at 80° C. The reaction was quenched with water, and extracted with three times with ethyl acetate. The combined organic layers were dried over MgSO4 and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by amine coated silica gel column chromatography (hexane:ethyl acetate=3:1) to give the title compound as an orange solid (107.9 mg, 70%).

後処理

  1. stirringstirred for 6 h at 80° C
  2. customThe reaction was quenched with water
  3. extractionextracted with three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customThe residue was purified by amine coated silica gel column chromatography (hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-0fcac1db94bd4ad88dc45d8f47fb7cd6
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07598393B2

反応ノート

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