1,2-Dibromoethane → 1-(4-Chlorocinnamyl)-4-(5-isoquinolinesulfonyl)piperazine

HRID 5742

反応式

HRID 5742 の反応式
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH:6]=[CH:7][CH2:8][NH:9][CH2:10][CH2:11][NH:12][S:13]([C:16]2[C:17]3[CH:18]=[CH:19][N:20]=[CH:21][C:22]=3[CH:23]=[CH:24][CH:25]=2)(=[O:15])=[O:14])=[CH:4][CH:3]=1.Br[CH2:29][CH2:30]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][CH2:8][N:9]2[CH2:30][CH2:29][N:12]([S:13]([C:16]3[C:17]4[CH:18]=[CH:19][N:20]=[CH:21][C:22]=4[CH:23]=[CH:24][CH:25]=3)(=[O:14])=[O:15])[CH2:11][CH2:10]2)=[CH:26][CH:27]=1

参加物

6

反応物 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 176156N-[2-(4-Chlorocinnamylamino)ethyl]-5-isoquinolinesulfonamide

生成物 1

HCID 542037031-(4-Chlorocinnamyl)-4-(5-isoquinolinesulfonyl)piperazine収率 25.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1.31 g of the product of Example 172 was dissolved in 3 ml of dimethylformamide, to the solution were added 644 mg of 1,2-dibromoethane and 1.13 g of anhydrous potassium carbonate at a room temperature, and the mixture was stirred for 24 hours. After adding 100 ml of ethyl acetate, the ethyl acetate layer was sequentially washed with water and a saturated sodium chloride aqueous solution twice in each case, and dried over magnesium sulfate. The solution was filtered and evaporated under a reduced pressure, and resulting residue was purified on a silica gel column (silica gel 50 g, eluant: 5% methanol in chloroform), to obtain 356 mg of the title compound in a colorless amorphous form, while recovering the residual starting material.

後処理

  1. washthe ethyl acetate layer was sequentially washed with water
  2. dry with materiala saturated sodium chloride aqueous solution twice in each case, and dried over magnesium sulfate
  3. filtrationThe solution was filtered
  4. customevaporated under a reduced pressure
  5. customresulting residue
  6. customwas purified on a silica gel column (silica gel 50 g, eluant: 5% methanol in chloroform)

出典と根拠

ORDレコード
ord-57a90189c8764512903a44bb9d37a3a5
出典データセット
uspto-grants-1993_09
特許番号
US05245034

関連ノート

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