Methyl morpholine oxide → 6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2,3-dihydroxy-propoxy)-amide

HRID 1010008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010008
[CH2:1]([O:4][NH:5][C:6]([C:8]1[C:17]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][C:20]=2[Cl:26])=[C:16]([F:27])[C:11]2[N:12]=[CH:13][N:14]([CH3:15])[C:10]=2[CH:9]=1)=[O:7])[CH:2]=[CH2:3].[O:28]1CCCC1.[OH2:33].C[N+]1([O-])CCOCC1.OS([O-])=O.[Na+]>C(OCC)(=O)C.O=[Os](=O)(=O)=O>[OH:33][CH:2]([CH2:3][OH:28])[CH2:1][O:4][NH:5][C:6]([C:8]1[C:17]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][C:20]=2[Cl:26])=[C:16]([F:27])[C:11]2[N:12]=[CH:13][N:14]([CH3:15])[C:10]=2[CH:9]=1)=[O:7]

Komponenten

7

Edukt 4

HCID 82029Methyl morpholine oxideHCID 111669156-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid allyloxy-amideHCID 21881883Oxolane--water (1/1)HCID 23665763Sodium Bisulfite

Produkt 1

HCID 103111226-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2,3-dihydroxy-propoxy)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid allyloxy-amide 29tt (20 mg, 0.04 mmol) in 0.50 mL 4:1 tetrahydrofuran/water is added OsO4 (41 μL, 0.054 M solution in t-BuOH, 0.002 mmol) followed by NMO (7 mg, 0.06 mmol). The solution is stirred at room temperature for eight hours after which time HPLC analysis showed complete conversion to product. The solution is then stirred with saturated NaHSO3 and diluted with ethyl acetate. The organic phase is dried (Na2SO4). Purification by FCC (DCM->20:1 DCM/MeOH) provided 16 mg desired product as an off-white solid. MS ESI (+) m/z 487, 489 (M+, Br pattern) detected.

Aufarbeitung

  1. dry with materialThe organic phase is dried (Na2SO4)
  2. customPurification by FCC (DCM->20:1 DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-72ed4eec95d44b6898dd1f90d1e3f107
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973170B2

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