Triethylamine → 3-Ethyl-7,8-dihydro-3H-pyrazolo[4',3':5,6]pyrido[3,4-d]pyridazine-6,9-dione

HRID 429048Notes

Reaction equation

HRID 429048 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:15]([OH:17])=O)[C:11]([C:12](O)=[O:13])=[C:6]2[CH:5]=[N:4]1)[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)[N:37]=[N:36]C=2C=1.C(N(CC)CC)C.NN>C1COCC1.O>[CH2:1]([N:3]1[C:7]2[N:8]=[CH:9][C:10]3[C:15](=[O:17])[NH:36][NH:37][C:12](=[O:13])[C:11]=3[C:6]=2[CH:5]=[N:4]1)[CH3:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 9321HydrazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183543231-Ethyl-1H-pyrazolo[3,4-b]pyridine-4,5-dicarboxylic acid

Product 1

HCID 109880883-Ethyl-7,8-dihydro-3H-pyrazolo[4',3':5,6]pyrido[3,4-d]pyridazine-6,9-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

An alternative method could be used by starting with 1-ethyl-1H-pyrazolo[3,4-b]pyridine-4,5-dicarboxylic acid. The diacid was dissolved in anhydrous THF with EDAC.HCl (1.2 eq), HOBT (1.2 eq), and triethylamine (5.0 eq). To this solution was added anhydrous hydrazine (2.0 eq). The resulting solution was stirred at rt for 5 h and then diluted with water. The precipitated solid was collected by filtration to afford the title compound as a white solid.

Workup

  1. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-2cba928d48a94f33903ca38741afb7d2
Source dataset
uspto-grants-2001_11
Patent number
US06316438B1

Reaction notes

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