Acetic Acid → 1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

HRID 2212959Notes

Reaction equation

HRID 2212959 reaction equation
C(O)(=O)C.[Cl-].[NH4+:6].[F:7][C:8]1[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=1[CH2:10][N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([C:20](=[NH:23])OC)=[N:12]1>CO>[F:7][C:8]1[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=1[CH2:10][N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([C:20]([NH2:6])=[NH:23])=[N:12]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 11243078Methyl 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbiMidate

Product 1

HCID 114039861-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

33.76 g (32.19 ml, 562 mmol) of glacial acetic acid and 9.28 g (173 mmol) of ammonium chloride are added to the solution of methyl (2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidate in methanol obtained from example 2E), and the mixture is stirred under reflux overnight. The solvent is evaporated in vacuo, the residue is thoroughly triturated with acetone, and the precipitated solid is filtered off with suction.

Workup

  1. temperatureunder reflux overnight
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is thoroughly triturated with acetone
  4. filtrationthe precipitated solid is filtered off with suction

Sources & evidence

ORD record
ord-9688ebb2ca02423c888026ba9906adae
Source dataset
uspto-grants-2006_09
Patent number
US07105523B2

Reaction notes

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