Phenylhydrazine → HCID 178490900, compound

HRID 1471808Notes

Reaction equation

HRID 1471808 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:14]=[CH:15][C:3]=12.[C:25]1([NH:31][NH2:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:13]2[C:4]3[NH:5][CH:6]=[C:7]4[C:8](=[O:10])[N:31]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:32]=[C:2]4[C:3]=3[CH:15]=[N:14]2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 7516PhenylhydrazineHCID 53665897Ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 178490900HCID 178490900, compound

Conditions

Temperature
90 °C

Procedure

A suspension of compound 3 and 10 equivalents of phenyl hydrazine was stirred at 90° C. for 16 hours. Reaction was quenched with iced water. The aqueous layer was removed, residue was suspended in ethanol and stirred with 1N NaOH solution at room temperature for 1 hour. pH was adjusted to 5 using acetic acid and solvent was removed in vacuo. Compound 4 was collected by filtration.

Workup

  1. customReaction
  2. customwas quenched with iced water
  3. customThe aqueous layer was removed
  4. stirringstirred with 1N NaOH solution at room temperature for 1 hour
  5. customwas removed in vacuo
  6. filtrationCompound 4 was collected by filtration

Sources & evidence

ORD record
ord-8d98d11e5c3041d38e21729098d05b86
Source dataset
uspto-grants-2015_04
Patent number
US09012470B2

Reaction notes

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