Ethylhydrazine → 4-Chloro-1-ethyl-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine

HRID 1525408Notes

Reaction equation

HRID 1525408 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[NH:14][N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]=12.[CH2:23](NN)[CH3:24]>>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][N:5]=[C:4]2[N:14]([CH2:23][CH3:24])[N:15]=[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:3]=12

Participants

3

Reactant 2

HCID 29062EthylhydrazineHCID 86697018CID 86697018

Product 1

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

Procedure

Compound 18 was synthesised following similar procedures outlined in Example 22 (Compound 9), using ethyl hydrazine instead of hydrazine hydrate in Step 3. As a slightly modified procedure, Step 3 was performed at 90° C. for 16 h in a sealed tube. Subsequently, the reaction mixture was partitioned between CH2Cl2 and water. The organic phase was separated using a phase separating cartridge and concentrated in vacuo. The crude residue was purified by column chromatography (silica gel, 5% ethyl acetate/isohexane) yielding Compound 18 as a solid.

Workup

  1. customCompound 18 was synthesised
  2. customSubsequently, the reaction mixture was partitioned between CH2Cl2 and water
  3. customThe organic phase was separated
  4. customseparating cartridge
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography (silica gel, 5% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-aa45429006c14269baea73c02b947b9d
Source dataset
uspto-grants-2015_07
Patent number
US09079909B2

Reaction notes

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