Methyl iodide → N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-5-isoquinolinesulfonamide

HRID 1090585

Reaction equation

HRID 1090585 reaction equation
[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.[CH3:28]I>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][CH2:8][N: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:14])=[O:15])[CH3:28])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 176156N-[2-(4-Chlorocinnamylamino)ethyl]-5-isoquinolinesulfonamide

Product 1

HCID 53675817N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-5-isoquinolinesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.50 g of the product of Example 172 was dissolved in 10 ml of chloroform, to the solution was added 3 ml of methyl iodide at a room temperature, and the mixture was stirred for 40 minutes. Excess methyl iodide was immediately evaporated off 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 720 mg of the title compound in a colorless amorphous form.

Workup

  1. customExcess methyl iodide was immediately evaporated off under a reduced pressure
  2. customresulting residue
  3. customwas purified on a silica gel column (silica gel 50 g, eluant: 5% methanol in chloroform)

Sources & evidence

ORD record
ord-9a35a85cc674415a888b7e3a55a21420
Source dataset
uspto-grants-1992_01
Patent number
US05081246

Linked notes

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