Methyl morpholine oxide → HCID 11181123, Verbindung

HRID 504197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504197
[CH:1]1([CH2:4][O:5][NH:6][C:7]([C:9]2[C:27]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=3[CH3:36])=[C:26]([F:37])[C:12]3[N:13]=[CH:14][N:15]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][S:23][CH2:22][CH2:21]4)[C:11]=3[CH:10]=2)=[O:8])[CH2:3][CH2:2]1.[OH2:38].CC(C)=O.C[OH:44].C[N+]1([O-])CCOCC1>S([O-])([O-])(=O)=S.[Na+].[Na+].C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[CH:1]1([CH2:4][O:5][NH:6][C:7]([C:9]2[C:27]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=3[CH3:36])=[C:26]([F:37])[C:12]3[N:13]=[CH:14][N:15]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][S:23](=[O:44])(=[O:38])[CH2:22][CH2:21]4)[C:11]=3[CH:10]=2)=[O:8])[CH2:3][CH2:2]1

Komponenten

7

Edukt 3

HCID 82029Methyl morpholine oxideHCID 112733356-(4-bromo-2-methyl-phenylamino)-7-fluoro-3-(4-thiomorpholin-4-yl-butyl)-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amideHCID 86590524Methanol water acetone

Produkt 1

HCID 11181123HCID 11181123, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 24477Sodium ThiosulfateLösungsmittel

Versuchsvorschrift

To a solution of 6-(4-bromo-2-methyl-phenylamino)-7-fluoro-3-(4-thiomorpholin-4-yl-butyl)-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide 181(8 mg, 0.014 mmol) in 1:1:1 water/acetone/MeOH (1 mL) is added NMO (1.6 mg, 0.014 mmol) and osmium tetroxide (250 μL, 0.054 M solution in t-BuOH, 0.014 mmol). After stirring for 24 hours, the solution is diluted with saturated sodium thiosulfate, stirred for 10 minutes and diluted with ethyl acetate. The solution is washed with brine (2×), dried (Na2SO4) and concentrated under reduced pressure to a grey solid. FCC (10:1 dichloromethane/methanol) provides 6 mg (71%) desired product as an off-white solid. MS ESI (+) m/z 622, 624 (M+, Br pattern) detected.

Aufarbeitung

  1. stirringstirred for 10 minutes
  2. washThe solution is washed with brine (2×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure to a grey solid

Quellen und Nachweise

ORD-Eintrag
ord-420db6aa12f84f1a881eb69ddcef21a4
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07777050B2

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