N,N-Dimethylethylenediamine → HCID 178483741, compound

HRID 234833Notes

Reaction equation

[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].CN(C)CC[N:11]1[C:19]2[CH:18]=[CH:17][C:16](Cl)=[C:15]3[C:21](=[O:28])[C:22]4[CH:23]=[N:24][CH:25]=[CH:26][C:27]=4[C:13]([C:14]=23)=[N:12]1>N1C=CC=CC=1>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:16]1[CH:17]=[CH:18][C:19]2[NH:11][N:12]=[C:13]3[C:27]4[CH:26]=[CH:25][N:24]=[CH:23][C:22]=4[C:21](=[O:28])[C:15]=1[C:14]=23

Participants

Conditions

Temperature: 80 °C

Procedure

Under a nitrogen atmosphere N,N-dimethylethylenediamine (1.79 mL) is added to a stirred solution of 2-[2-(dimethylamino)ethyl]-5-chloroisoquino[5,6,7-cd]indazole-6(2H)-one of Example 8 (0.539 g) in pyridine (6.80 mL) and the resulting solution is heated at 80° C. for 12 hours. The pyridine and excess N,N-dimethylethylenediamine are removed by roto-evaporation and the obtained residue is purified by silica gel column chromatography eluting first with methylene chloride, then with methylene chloride/methanol 95/5 and finally with methylene chloride/methanol/concd. ammonia from 95/5/0.5 to 95/5/1 v/v/v. The fractions containing the yellow desired product are pooled and the solvents roto-evaporated. The obtained residue (0.529 g) is crystallized from diisopropylether to give 2-[2-(dimethylamino)ethyl)]-5-[[2-(dimethylamino)ethyl]amino]isoquino[5,6,7-cd]indazole-6(2H)-one as a yellow powder (0.291 g).

Workup

customThe pyridine and excess N,N-dimethylethylenediamine are removed by roto-evaporation
customthe obtained residue is purified by silica gel column chromatography
washeluting first with methylene chloride
additionThe fractions containing the yellow desired product
customthe solvents roto-evaporated
customThe obtained residue (0.529 g) is crystallized from diisopropylether

Sources & evidence

ORD record: ord-957c16f04e9542a98bc18cfc20d982ac
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05596097

Reaction notes

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