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

HRID 720257
Notes
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Reaction equation

HRID 720257 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14](=[NH:17])OC)=[N:6]1.C(O)(=O)C.[Cl-].[NH4+:27]>CO>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14](=[NH:27])[NH2:17])=[N:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

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

The solution of methyl (2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidate in methanol obtained from Example 33 A-5 is mixed with 33.76 g (32.19 ml, 562 mmol) of glacial acetic acid and 9.28 g (173 mmol) of ammonium chloride and 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-ce3b684477a84da69db3f2854e91f04e
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07135474B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes