Sodium hydride → 5-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-N-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethyl]-benzenesulfonamide

HRID 2242811ノート

反応式

HRID 2242811 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:7]([S:9]([NH:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])(=[O:11])=[O:10])[CH:8]=1)#[N:2].Br[CH2:28][CH2:29][N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].[H-].[Na+]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:18][C:19]2[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=2)=[C:7]([S:9]([N:12]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH2:28][CH2:29][N:30]2[C:34](=[O:35])[CH2:33][CH2:32][C:31]2=[O:36])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 135613951-(2-Bromoethyl)pyrrolidine-2,5-dioneHCID 592083045-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-benzenesulfonamide

生成物 1

HCID 111919305-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-N-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethyl]-benzenesulfonamide収率 81.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 5-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-benzene-sulfonamide (41.4 mg, 0.1 mmol) in dry DMF (2 ml) was added 1-(2-bromo-ethyl)-pyrrolidine-2,5-dione (30.9 mg, 0.15 mmol) and NaH (60%, 6.00 mg, 0.15 mmol). The mixture was stirred for 8 hours at 90° C. After cooled to room temperature, the solvent was evaporated. The mixture was diluted with EtOAc (60 ml), washed with brine, and dried over MgSO4. The solvent was evaporated and the residue was purified by preparative TLC (CH2Cl2/CH3OH=20/1) to give 5-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-N-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethyl]-benzenesulfonamide (44 mg, 81.6%) and the free base was converted into HCl salt by 4N HCl in dioxane.

後処理

  1. temperatureAfter cooled to room temperature
  2. customthe solvent was evaporated
  3. additionThe mixture was diluted with EtOAc (60 ml)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated
  7. customthe residue was purified by preparative TLC (CH2Cl2/CH3OH=20/1)

出典と根拠

ORDレコード
ord-33dfae9ddd17442dbf6ecbea0c5a5d09
出典データセット
uspto-grants-2010_03
特許番号
US07674797B2

反応ノート

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