(Diethylamino)sulfur trifluoride → HCID 178461108, Verbindung

HRID 13364

Reaktionsgleichung

Reaktionsgleichung von HRID 13364
C(N(S(F)(F)[F:7])CC)C.[CH3:10][S:11]([C:14]1[CH:43]=[CH:42][C:17]([O:18][C:19]2[C:20]([N:34]3[CH2:38][CH2:37][CH2:36][CH:35]3[CH:39](O)[CH3:40])=[CH:21][C:22]3[NH:26][C:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)=[N:24][C:23]=3[CH:33]=2)=[CH:16][CH:15]=1)(=[O:13])=[O:12].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[F:7][CH:39]([CH:35]1[CH2:36][CH2:37][CH2:38][N:34]1[C:20]1[C:19]([O:18][C:17]2[CH:42]=[CH:43][C:14]([S:11]([CH3:10])(=[O:13])=[O:12])=[CH:15][CH:16]=2)=[CH:33][C:23]2[NH:24][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[N:26][C:22]=2[CH:21]=1)[CH3:40]

Komponenten

5

Edukt 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 231453781-(1-(6-(4-Methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-2-yl)-ethanol

Produkt 1

HCID 178461108HCID 178461108, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

0.007 ml of diethylaminosulfur trifluoride was added to a chloroform (1 ml) solution of 21 mg of 1-(1-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-2-yl)-ethanol diastereomer A obtained in Example 354, at −78° C., and the reaction liquid was stirred at −78° C. for 1 hour. The reaction liquid was heated up to room temperature, and aqueous saturated sodium bicarbonate was added to the reaction liquid, and then extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was 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 solid.

Aufarbeitung

  1. customA obtained in Example 354, at −78° C.
  2. customthe reaction liquid
  3. customThe reaction liquid
  4. temperaturewas heated up to room temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated away
  8. customthe resulting residue was purified
  9. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-24f8fe4802174c569b9c21dcebe30083
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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