Sodium Chloride → 1-[N,O-Bis(5-Isoquinolinesulphonyl)Tyrosyl]-4-(3-Phenylpropyl)Piperazine

HRID 1587184Notes

Reaction equation

HRID 1587184 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([NH:14][C@H:15]([C:37]([N:39]3[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]3)=[O:38])[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][S:24]([C:27]4[C:28]5[CH:29]=[CH:30][N:31]=[CH:32][C:33]=5[CH:34]=[CH:35][CH:36]=4)(=[O:26])=[O:25])=[CH:19][CH:18]=3)(=[O:13])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.[C:45]1([CH2:51][CH2:52][CH2:53]Br)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[Cl-].[Na+]>CN(C)C=O>[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([NH:14][C@H:15]([C:37]([N:39]3[CH2:40][CH2:41][N:42]([CH2:53][CH2:52][CH2:51][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[CH2:43][CH2:44]3)=[O:38])[CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][S:24]([C:27]4[C:28]5[CH:29]=[CH:30][N:31]=[CH:32][C:33]=5[CH:34]=[CH:35][CH:36]=4)(=[O:26])=[O:25])=[CH:21][CH:22]=3)(=[O:12])=[O:13])[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 542919501-[N,O-Bis(5-Isoquinolinesulfonyl)Tyrosyl]Piperazine

Product 1

HCID 538846271-[N,O-Bis(5-Isoquinolinesulphonyl)Tyrosyl]-4-(3-Phenylpropyl)PiperazineYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

301 mg of the crude product obtained in Example 28 and 95 mg of 3-phenylpropyl bromide were dissolved in 5 ml of dimethylformamide, and to the solution were added 66 mg of potassium carbonate and 72 mg of sodium iodide. After stirring at 80° C. for 7 hours, 30 ml of saturated sodium chloride was added to the reaction mixture, which was then extracted with 40 ml of ethyl acetate, and the extract was washed with 30 ml of saturated sodium chloride aqueous solution, dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting residue was applied to a silica gel column and eluted with chloroform/methanol (40:1) to obtain 216 mg of the title compound in a yellow amorphous form.

Workup

  1. extractionwas then extracted with 40 ml of ethyl acetate
  2. washthe extract was washed with 30 ml of saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. washeluted with chloroform/methanol (40:1)

Sources & evidence

ORD record
ord-7b31ed91afb745b4b7a8387908f4057f
Source dataset
uspto-grants-1993_06
Patent number
US05216150

Reaction notes

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