N,N-Dimethylethylenediamine → 2-methyl-5-[[2-(dimethylamino)ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one

HRID 234829Notes

Reaction equation

HRID 234829 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[CH3:7][N:8]1[C:16]2[CH:15]=[CH:14][C:13](OS(C3C=CC(C)=CC=3)(=O)=O)=[C:12]3[C:28](=[O:35])[C:29]4[CH:30]=[CH:31][N:32]=[CH:33][C:34]=4[C:10]([C:11]=23)=[N:9]1>N1C=CC=CC=1>[CH3:7][N:8]1[C:16]2[CH:15]=[CH:14][C:13]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[C:12]3[C:28](=[O:35])[C:29]4[CH:30]=[CH:31][N:32]=[CH:33][C:34]=4[C:10]([C:11]=23)=[N:9]1

Participants

4

Reactant 2

HCID 66053N,N-Dimethylethylenediamine2×HCID 153378742-methyl-5-(p-toluenesulfonyloxy)isoquino [8,7,6-cd]indazole-6(2H)-one

Product 1

HCID 153378752-methyl-5-[[2-(dimethylamino)ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A 1M solution of N,N-dimethylethylenediamine in pyridine (0.10 mL) is added to a stirred suspension of 2-methyl-5-(p-toluenesulfonyloxy)isoquino[8,7,6-cd]indazole-6(2H)-one of Example 1 (0.02 g) in dry pyridine (2 mL). After stirring at room temperature for one hour the reaction mixture is heated at 70° C. for 13 hours while additional amounts of N,N-dimethylethylenediamine solution (0.1; 0.05; 0.05 mL) are added after 2, 4 and 11 hours respectively. Pyridine and excess N,N-dimethylethylenediamine are removed by distillation at reduced pressure and the obtained residue is partitioned between CH2Cl2 (50 mL) and brine (10 mL) to which NaHCO3 saturated solution is added (1 mL). The organic solution is dried over anhydrous Na2SO4 and the solvent removed by distillation. The orange residue obtained is purified by silica-gel column chromatography (eluant: CHCl3 /MeOH 95/5 (30 mL) followed by CHCl3 /MeOH/NH4OH 90/15/0.5 (50 mL) to give 2-methyl-5-[[2-(dimethylamino)ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one (0.011 g) as a reddish orange solid.

Workup

  1. additionare added after 2, 4 and 11 hours respectively
  2. customPyridine and excess N,N-dimethylethylenediamine are removed by distillation at reduced pressure
  3. customthe obtained residue is partitioned between CH2Cl2 (50 mL) and brine (10 mL) to which NaHCO3 saturated solution
  4. additionis added (1 mL)
  5. dry with materialThe organic solution is dried over anhydrous Na2SO4
  6. customthe solvent removed by distillation
  7. customThe orange residue obtained
  8. customis purified by silica-gel column chromatography (eluant

Sources & evidence

ORD record
ord-8e1d664783884956b66a8ce20cd70fdc
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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