Methyl morpholine oxide → HCID 11181123, compound

HRID 216451Notes

Reaction equation

HRID 216451 reaction equation
[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

Participants

7

Reactant 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

Product 1

HCID 11181123HCID 11181123, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-abd12002213f4f958dff15194f4dba98
Source dataset
uspto-grants-2012_06
Patent number
US08193229B2

Reaction notes

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