N,N-Dimethylethylenediamine → 10-p-Methoxybenzyloxy-5-[[2-(dimethylamino)ethyl]amino]-2-methylisoquino [5,6,7-cd]indazole-6(2H)-one

HRID 234834Notes

Reaction equation

HRID 234834 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:26]3[C:17]4=[N:18][N:19]([CH3:25])[C:20]5[CH:21]=[CH:22][C:23](Cl)=[C:15]([C:16]=54)[C:14](=[O:27])[C:13]=3[CH:12]=[N:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH2:34]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:26]3[C:17]4=[N:18][N:19]([CH3:25])[C:20]5[CH:21]=[CH:22][C:23]([NH:34][CH2:33][CH2:32][N:31]([CH3:35])[CH3:30])=[C:15]([C:16]=54)[C:14](=[O:27])[C:13]=3[CH:12]=[N:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 1071628110-(p-Methoxybenzyloxy)-5-chloro-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one

Product 1

HCID 1074250010-p-Methoxybenzyloxy-5-[[2-(dimethylamino)ethyl]amino]-2-methylisoquino [5,6,7-cd]indazole-6(2H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 10-(p-methoxybenzyloxy)-5-chloro-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one of Example 11 (0.053 g) and N,N-dimethylethylenediamine (0,115 g) in pyridine (0.5 mL) is heated at 120° C. for 3.5 h under a nitrogen atmosphere. The excess diamine and pyridine are removed by a slow stream of nitrogen gas and the resultant dark orange residue is placed under vacuo for 3 h. The crude material is purified by radial chromathography (silica gel, 2 mm thickness) using gradient elution commencing with 2% methanol/98% chloroform (100 mL) to mixtures containing 4% methanol (75 mL) to 6% methanol (60 mL). Upon removal of the 4% methanol (96% chloroform eluent, starting material is recovered (10 mg). Removal of the 6% methanol/94% chloroform eluent led to 10-p-methoxybenzyloxy-5-[[2-(dimethylamino)ethyl]amino]-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one as a pure product (22 mg).

Workup

  1. customThe excess diamine and pyridine are removed by a slow stream of nitrogen gas
  2. customThe crude material is purified by radial chromathography (silica gel, 2 mm thickness)
  3. washgradient elution
  4. additioncontaining 4% methanol (75 mL) to 6% methanol (60 mL)
  5. customUpon removal of the 4% methanol (96% chloroform eluent
  6. customis recovered (10 mg)
  7. customRemoval of the 6% methanol/94% chloroform eluent

Sources & evidence

ORD record
ord-ad7b9b44682e44c7836759bf272d176b
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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