2-Hydrazinoethanol → 2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethan-1-ol

HRID 1525409Notes

Reaction equation

HRID 1525409 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.[OH:25]CCNN>>[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][CH2:24][OH:25])[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 80172-HydrazinoethanolHCID 665768074-Chloro-1-ethyl-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine

Product 1

HCID 665767242-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethan-1-ol

Procedure

Compound 7 was synthesised following similar procedures outlined in Example 31 (Compound 18), using 2-hydroxyethyl hydrazine instead of ethyl hydrazine in Step 3. As a slightly modified procedure, Step 3 was performed at 90° C. for 30 min in the microwave. The crude residue was purified by column chromatography (silica gel, gradient 10 to 50% ethyl acetate/isohexane), yielding Compound 7 as a solid.

Workup

  1. customCompound 7 was synthesised
  2. customThe crude residue was purified by column chromatography (silica gel, gradient 10 to 50% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-8b8d2e64398f4d168f49cc67bc079321
Source dataset
uspto-grants-2015_07
Patent number
US09079909B2

Reaction notes

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