Cesium carbonate → trans-1-(4-acetoxy-2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13350

Reaktionsgleichung

Reaktionsgleichung von HRID 13350
[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][C@@H:24]([O:26][C:27](=[O:29])[CH3:28])[CH2:23][C@@H:22]1[C:30]1[CH:35]=[C:34]([N+:36]([O-])=O)[C:33]([NH:39][C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)=O)=[CH:32][C:31]=1F)(=[O:20])[CH3:19].O.O.[Sn](Cl)Cl>C(OCC)(=O)C.CN(C)C=O>[C:27]([O:26][C@@H:24]1[CH2:25][N:21]([C:18](=[O:20])[CH3:19])[C@@H:22]([C:30]2[C:31]([O:11][C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=3)=[CH:32][C:33]3[N:39]=[C:40]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=4)[NH:36][C:34]=3[CH:35]=2)[CH2:23]1)(=[O:29])[CH3:28]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 61436Stannous chloride dihydrateHCID 1233504-(Methylsulfonyl)phenolHCID 67483055trans-1-Acetyl-2-(5-nitro-2-fluoro-4-((pyridin-2-carbonyl)-amino)-phenyl)-4-acetoxy-pyrrolidine

Produkt 1

HCID 67483003trans-1-(4-acetoxy-2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

10 mg of 4-methanesulfonyl-phenol and 20 mg of cesium carbonate were added to a dimethylformamide (0.5 ml) solution of 21 mg of trans-1-acetyl-2-(5-nitro-2-fluoro-4-((pyridin-2-carbonyl)-amino)-phenyl)-4-acetoxy-pyrrolidine, and the reaction liquid was stirred at 90° C. for 1 hour. 100 mg of tin(II) chloride dihydrate was added to it, and the reaction liquid was stirred at 90° C. for 5 hours. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound as a yellow oily substance.

Aufarbeitung

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred at 90° C. for 5 hours
  4. customThe reaction liquid
  5. washwashed with water and saturated saline in order
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customto obtain the entitled compound as a yellow oily substance

Quellen und Nachweise

ORD-Eintrag
ord-a92d6190786d4e50ab259348df0d02ec
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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