Benzylhydrazine dihydrochloride → 1-Benzyl-4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine

HRID 1775543Notes

Reaction equation

HRID 1775543 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH2:23][CH3:24])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]=12.Cl.Cl.C(NN)[C:28]1[CH:33]=[CH:32]C=[CH:30][CH:29]=1>>[CH2:23]([N:14]1[C:4]2=[N:5][N:6]=[C:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]([Cl:1])=[C:3]2[C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:15]1)[C:24]1[CH:32]=[CH:33][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 146540Benzylhydrazine dihydrochlorideHCID 665768074-Chloro-1-ethyl-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine

Product 1

HCID 665769681-Benzyl-4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine

Procedure

Compound 31 was synthesised following similar procedures outlined in Example 31 (Compound 18), using benzyl hydrazine dihydrochloride instead of ethyl hydrazine in Step 3. As a slightly modified procedure, Step 3 was performed at 50° C. for 16 h. The crude residue was purified by column chromatography (silica gel, gradient 5 to 10% ethyl acetate/isohexane), followed by preparative HPLC, yielding Compound 31 as a solid.

Workup

  1. customCompound 31 was synthesised
  2. customThe crude residue was purified by column chromatography (silica gel, gradient 5 to 10% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-83d0ec89079e4488be432038a9e984a0
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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