Methyl morpholine oxide → HCID 11181123、化合物

HRID 31991ノート

反応式

HRID 31991 の反応式
[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

参加物

7

反応物 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

生成物 1

HCID 11181123HCID 11181123、化合物収率 71%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 8857Ethyl Acetate溶媒HCID 24477Sodium Thiosulfate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-038ade63a58e4a4a953703c9ec2daa8b
出典データセット
uspto-grants-2008_09
特許番号
US07425637B2

反応ノート

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