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

HRID 217022ノート

反応式

HRID 217022 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-839e7e3adba846abae212c19253f9df4
出典データセット
uspto-grants-2012_06
特許番号
US08193231B2

反応ノート

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