N,N-Dimethylethylenediamine → HCID 178483740, compound

HRID 1451485Notes

Reaction equation

HRID 1451485 reaction equation
CN(C)CC[N:5]1[C:13]2[CH:12]=[CH:11][C:10](OS(C3C=CC(C)=CC=3)(=O)=O)=[C:9]3[C:25](=[O:32])[C:26]4[CH:27]=[CH:28][N:29]=[CH:30][C:31]=4[C:7]([C:8]=23)=[N:6]1.[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH2:38]>N1C=CC=CC=1>[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH:38][C:10]1[CH:11]=[CH:12][C:13]2[NH:5][N:6]=[C:7]3[C:31]4[CH:30]=[N:29][CH:28]=[CH:27][C:26]=4[C:25](=[O:32])[C:9]=1[C:8]=23

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 10600131HCID 10600131, compound

Product 1

HCID 178483740HCID 178483740, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-[2-(dimethylamino)ethyl]-5-(p-toluenesulfonyloxy)isoquino[8,7,6-cd]indazole-6(2H)-one of Example 2 (0.463 g) and 2-(dimethylamino)ethylamine (0.80 mL) in dry pyridine (4.63 mL) is heated at 80° C. for 1 h, 30' under a nitrogen blanket. The solution is then concentrated to dryness and the dark residue obtained is partitioned between brine (30 mL) and ethyl acetate (4×25 mL). The combined organic solutions are dried over Na2SO4 and concentrated to about 3 mL. After addition of n-hexane (12 mL) and stirring for one hour the precipitate is collected by suction and dried at 40° C. under vacuum to give 2-[2-(dimethylamino)ethyl)]5-[[2-(dimethylamino)ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one (0.23 g).

Workup

  1. concentrationThe solution is then concentrated to dryness
  2. customthe dark residue obtained
  3. customis partitioned between brine (30 mL) and ethyl acetate (4×25 mL)
  4. dry with materialThe combined organic solutions are dried over Na2SO4
  5. concentrationconcentrated to about 3 mL
  6. additionAfter addition of n-hexane (12 mL)
  7. customis collected by suction
  8. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-31d5091ea9d94e0495aedc292299c319
Source dataset
uspto-grants-1997_02
Patent number
US05604246

Reaction notes

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