Methyl morpholine oxide → HCID 11181123, 화합물

HRID 1010015노트

반응식

HRID 1010015 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 11181123HCID 11181123, 화합물수율 71%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 8857Ethyl Acetate용매HCID 24477Sodium Thiosulfate용매

실험 절차

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 18l (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.

후처리

  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

출처 및 근거

ORD 기록
ord-a73d94f86cf14d24a9d154824229ba26
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973170B2

반응 노트

불러오는 중…