Water → Bms-777607

HRID 42724

反応式

HRID 42724 の反応式
[Cl:1][C:2]1[C:3](C(N)=O)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[C:19](=[O:34])[N:20]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:21]=[CH:22][C:23]=2OCC)=[O:17])=[CH:11][C:10]=1[F:35].O.[C:40]([OH:43])(=O)[CH3:41].C(O)(=O)C.IC1C=CC=CC=1.C(#[N:57])C>C(OCC)(=O)C>[NH2:57][C:3]1[C:2]([Cl:1])=[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[C:19](=[O:34])[N:20]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[CH:21]=[CH:22][C:23]=3[O:43][CH2:40][CH3:41])=[O:17])=[CH:11][C:10]=2[F:35])[CH:6]=[CH:5][N:4]=1

参加物

6

反応物 4

HCID 962WaterHCID 6342AcetonitrileHCID 12217721Iodo benzene diacetateHCID 252319783-Chloro-4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2-fluorophenoxy)picolinamide

生成物 1

HCID 24794418Bms-777607収率 74%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To 3-chloro-4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2-fluorophenoxy)picolinamide (1.2 g, 2.1 mmol) in ethyl acetate (16 mL), acetonitrile (16 mL), and water (8 mL) at 0° C. was added iodobenzene diacetate (820 mg, 2.6 mmol, Aldrich). After stirring at rt for 2 h, the reaction was filtered to collect the crude product. The solid was washed with additional ethyl acetate. The filtrate was washed with saturated aqueous sodium bicarbonate solution and the organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The precipitate and filtrate were combined and purified by flash chromatography on silica gel (2% methanol/chloroform) to give the title compound (810 mg, 74%) as a white solid. 1H NMR (DMSO-d6) δ 10.57 (s, 1H), 7.83-7.79 (m, 2H), 7.67 (d, 1H, J=5.6 Hz), 7.41-7.38 (m, 3H), 7.36-7.22 (m, 3H), 6.44 (d, 1H, J=7.6 Hz), 6.36 (br s, 2H), 5.86 (d, 1H, J=6.0 Hz), 4.18 (q, 2H, J=7.2 Hz), 1.23 (t, 3H, J=7.2 Hz); MS(ESI+) m/z 513.09 (M+H)+.

後処理

  1. filtrationthe reaction was filtered
  2. customto collect the crude product
  3. washThe solid was washed with additional ethyl acetate
  4. washThe filtrate was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel (2% methanol/chloroform)

出典と根拠

ORDレコード
ord-271eb0c4e7fe42b0bde8c2e4c11af705
出典データセット
uspto-grants-2013_09
特許番号
US08536200B2

関連ノート

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