Acetic Acid → 2,3-Dichloro-N-[5-(hydroxymethyl)-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide

HRID 1444042ノート

反応式

HRID 1444042 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[S:15]([NH:18][C:19]1[N:20]=[CH:21][C:22]([C:33](OC)=[O:34])=[N:23][C:24]=1[O:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)(=[O:17])=[O:16].C(O)(=O)C>O1CCCC1>[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[S:15]([NH:18][C:19]1[C:24]([O:25][CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[N:23][C:22]([CH2:33][OH:34])=[CH:21][N:20]=1)(=[O:17])=[O:16]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 21226445Aluminium lithium hydrideHCID 59168105HCID 59168105、化合物

生成物 1

HCID 591682022,3-Dichloro-N-[5-(hydroxymethyl)-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide収率 42.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-65 °C

実験手順

Lithium aluminium hydride (0.85 mL of a 1M solution in tetrahydrofuran) was added dropwise to 5-(2,3-dichlorobenzenesulphonylamino)-6-(3-pyridinylmethoxy)pyrazine-2-carboxylic acid, methyl ester (Example 134) (0.2 g) in tetrahydrofuran (10 mL) cooled to −65° C. The reaction mixture was allowed to warm to room temperature and stirred for 1h. Aqueous acetic acid was added and the mixture extracted with ethyl acetate. The organic solution was dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/methanol mixtures gave the title compound (0.08 g).

後処理

  1. temperatureto warm to room temperature
  2. extractionthe mixture extracted with ethyl acetate
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customevaporated

出典と根拠

ORDレコード
ord-34fa62a8e8954656841e510c9930ab45
出典データセット
uspto-grants-2010_02
特許番号
US07662825B2

反応ノート

読み込み中…