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

HRID 5742

반응식

HRID 5742 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 542037031-(4-Chlorocinnamyl)-4-(5-isoquinolinesulfonyl)piperazine수율 25.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-57a90189c8764512903a44bb9d37a3a5
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245034

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