Water → 4-((2S)-2-((5-Isoquinolinylsulfonyl)methylamino)-3-oxo-3-(4-phenyl-1-piperazinyl)propyl)phenyl 5-isoquinolinesulfonate

HRID 5728Notes

Reaction equation

HRID 5728 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][N:42]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[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.[H-].[Na+].[CH3:53]I.O>CN(C)C=O>[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([N:14]([CH3:53])[C@H:15]([C:37]([N:39]3[CH2:40][CH2:41][N:42]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=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:25])=[O:26])=[CH:21][CH:22]=3)(=[O:12])=[O:13])[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53823674HCID 53823674, compound

Product 1

HCID 53121264-((2S)-2-((5-Isoquinolinylsulfonyl)methylamino)-3-oxo-3-(4-phenyl-1-piperazinyl)propyl)phenyl 5-isoquinolinesulfonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.27 g of the amorphous compound obtained in Example 108 was dissolved in 30 ml of dimethylformamide, to the solution were sequentially added 160 mg of 60% sodium hydride and 0.3 ml of methyl iodide with ice cooling, and the mixture was stirred for 90 minutes with ice cooling. After adding 80 ml of water, the reaction mixture was extracted with 100 ml of ethyl acetate, and the extract was washed with 80 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 (60:1), to obtain 1.8 g of the title compound in a yellow amorphous form.

Workup

  1. extractionthe reaction mixture was extracted with 100 ml of ethyl acetate
  2. washthe extract was washed with 80 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 (60:1)

Sources & evidence

ORD record
ord-dfeb66b2e0614f0e93caf3ee661eaf60
Source dataset
uspto-grants-1993_09
Patent number
US05245034

Reaction notes

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