Hydrochloric Acid → 2-[2-(amino)ethyl]-5-[[2-(amino)ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one trihydrochloride

HRID 234835Notes

Reaction equation

HRID 234835 reaction equation
[ClH:1].C(OC([NH:9][CH2:10][CH2:11][N:12]1[C:20]2[CH:19]=[CH:18][C:17]([NH:21][CH2:22][CH2:23][NH:24]C(OC(C)(C)C)=O)=[C:16]3[C:32](=[O:39])[C:33]4[CH:34]=[CH:35][N:36]=[CH:37][C:38]=4[C:14]([C:15]=23)=[N:13]1)=O)(C)(C)C>C(O)C>[ClH:1].[ClH:1].[ClH:1].[NH2:9][CH2:10][CH2:11][N:12]1[C:20]2[CH:19]=[CH:18][C:17]([NH:21][CH2:22][CH2:23][NH2:24])=[C:16]3[C:32](=[O:39])[C:33]4[CH:34]=[CH:35][N:36]=[CH:37][C:38]=4[C:14]([C:15]=23)=[N:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 108158792-[2-(N-tert-butoxycarbonylamino)ethyl]-5-[[2-(N-tert-butoxycarbonylamino)ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one

Product 1

HCID 199747312-[2-(amino)ethyl]-5-[[2-(amino)ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one trihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Under a nitrogen atmosphere an ethanolic solution of anhydrous HCl (5N; 0.40 mL) is dropped into a stirred suspension of 2-[2-(N-tert-butoxycarbonylamino) ethyl]-5-[[2-(N-tert-butoxycarbonylamino) ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one of Example 20 (0.104 g) in absolute ethanol (2.1 mL). Initial dissolution of the starting material followed by precipitation of a dark-red solid is observed during the addition of ethanolic HCI. This solid is redissolved with absolute ethanol and the solution is heated to 40° C. for 2 h, 30'. The gradual formation of a redamaranth precipitate is observed during the heating. After cooling to room temperature diethyl ether (10 mL) is added and the precipitate is collected by suction filtration under a nitrogen blanket, to give 2-[2-(amino)ethyl]-5-[[2-(amino)ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one trihydrochloride (0.070 g).

Workup

  1. dissolutionInitial dissolution of the starting material
  2. customfollowed by precipitation of a dark-red solid
  3. additionis observed during the addition of ethanolic HCI
  4. dissolutionThis solid is redissolved with absolute ethanol
  5. temperatureAfter cooling to room temperature diethyl ether (10 mL)
  6. additionis added
  7. filtrationthe precipitate is collected by suction filtration under a nitrogen blanket

Sources & evidence

ORD record
ord-9e1bfebc22bf4f6f8c0d98280c2d7cb8
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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