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2-Thiophenecarboxaldehyde → 1-Isopropylsulfonyl-2-amino-6-(2-(thien-2-yl)-5-(phenyl)-imidazol-4-yl)-benzimidazole methanesulfonate

HRID 2252063
ノート
印刷プレビュー

反応式

HRID 2252063 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].[CH:8]([S:11]([N:14]1[C:18]2[CH:19]=[C:20]([C:23](=O)[CH:24](O[Si](C(C)(C)C)(C)C)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH2:40])(=[O:13])=[O:12])([CH3:10])[CH3:9].C([O-])(=O)C.[NH4+:45].[Cl-].[NH4+:47].[OH-].[NH4+]>C(O)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CO.C(OCC)(=O)C>[CH3:8][S:11]([OH:13])(=[O:7])=[O:12].[CH:8]([S:11]([N:14]1[C:18]2[CH:19]=[C:20]([C:23]3[N:45]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[NH:47][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH2:40])(=[O:13])=[O:12])([CH3:10])[CH3:9]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

HCID 73642-ThiophenecarboxaldehydeHCID 14923Ammonium Hydroxide2 回HCID 25517Ammonium ChlorideHCID 517165Ammonium AcetateHCID 11340754HCID 11340754、化合物

生成物 1

HCID 179817351-Isopropylsulfonyl-2-amino-6-(2-(thien-2-yl)-5-(phenyl)-imidazol-4-yl)-benzimidazole methanesulfonate
収率 40%

試薬・触媒・溶媒 4

HCID 8895Cupric acetate触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
97.5 °C

実験手順

Add thiophene-2-carboxaldehyde (3.16 mL, 33.8 mmol) to a stirring mixture of 1-isopropylsulfonyl-2-amino-6-(α-((tert-butyldimethylsilyl)oxy)-α-(phenyl)acetyl)-benzimidazole (15.0 g, 30.8 mmol), copper(II) acetate (11.2 g, 61.5 mmol), and ammonium acetate (23.7 g, 308 mmol) in acetic acid (300 mL). Heat the mixture at 95-100° C. and stir vigorously for 2 hours. Cool the mixture to 15° C., pour into a mixture of 750 mL saturated aqueous ammonium chloride and 250 mL concentrated ammonium hydroxide. Adjust the mixture to pH 10 with ammonium hydroxide precooled to 5° C. and then add 4 L 4:1 ethyl acetate:methanol. Separate the layers and wash the organic layer with saturated aqueous ammonium chloride (500 mL), dry over magnesium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography eluting with dichloromethane containing from 15-50% acetonitrile and 0.5% triethylamine. Suspend the recovered material in ethanol (75 mL), warm to 55-60° C. for 30 minutes, cool to −10° C. for 30 minutes, filter, wash sequentially with cold ethanol followed by diethyl ether. Dry under reduced pressure to provide the title compound in 40% yield as a dark yellow powder. MS(ES+): m/z=464.1 (M+H)+

後処理

  1. temperatureCool the mixture to 15° C.
  2. customprecooled to 5° C.
  3. customSeparate the layers
  4. washwash the organic layer with saturated aqueous ammonium chloride (500 mL)
  5. dry with materialdry over magnesium sulfate
  6. concentrationconcentrate under reduced pressure
  7. washeluting with dichloromethane containing from 15-50% acetonitrile and 0.5% triethylamine
  8. temperaturewarm to 55-60° C. for 30 minutes
  9. temperaturecool to −10° C. for 30 minutes
  10. filtrationfilter
  11. washwash sequentially with cold ethanol
  12. customDry under reduced pressure

出典と根拠

ORDレコード
ord-3583828766e1418fbdb49f24ee9c01b6
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07320995B2

反応ノート

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