Water → 3-(4-Chlorocinnamylamino)-2-(5-isoquinolinesulfonylamino)pyridine

HRID 5736Notes

Reaction equation

HRID 5736 reaction equation
[ClH:1].[CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.C[N:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)C.O.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[Cl:1][C:5]1[CH:6]=[CH:11][C:28]([CH:29]=[CH:30][CH2:31][NH:26][C:24]2[C:19]([NH:17][S:12]([C:7]3[C:6]4[CH:5]=[CH:4][N:3]=[CH:2][C:11]=4[CH:10]=[CH:9][CH:8]=3)(=[O:14])=[O:13])=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:27][CH:4]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 218852-DimethylaminopyridineHCID 13116932Isoquinoline-5-sulfonyl chloride hydrochloride

Product 1

HCID 540830123-(4-Chlorocinnamylamino)-2-(5-isoquinolinesulfonylamino)pyridine

Procedure

4.52 g of the crystals obtained in Reference Example 41 was dissolved in 50 ml of pyridine, to the solution were added 5.8 g of 5-isoquinolinesulfonyl chloride hydrochloride and 3 g of dimethylaminopyridine, and the mixture was stirred for 18 hours at a room temperature, after adding 150 ml of water, extracted twice with 80 ml of chloroform. The extract was dried over magnesium sulfate and concentrated under a reduced pressure, and resulting residue was applied to a silica gel column and eluted with chloroform/methanol (100:1), and resulting crystals was washed with ethyl acetate, to obtain 1.2 g of the title compound as yellow crystals.

Workup

  1. extractionextracted twice with 80 ml of chloroform
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customresulting residue
  5. washeluted with chloroform/methanol (100:1)
  6. customresulting crystals
  7. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-06bb6720d27140e6bd8fead9cef0ffdf
Source dataset
uspto-grants-1993_09
Patent number
US05245034

Reaction notes

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