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

HRID 2307851Notes

Reaction equation

HRID 2307851 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>>[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

4

Reactant 3

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 11243078Methyl 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbiMidate2×

Product 1

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

Procedure

The solution of methyl (2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidate in methanol obtained from Example VII is admixed 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 under reduced pressure, the residue is triturated thoroughly with acetone and the precipitated solid is filtered off with suction. The solid is added to 2 l of water, admixed with stirring with 31.8 g of sodium carbonate and extracted three times with a total of 1 l of ethyl acetate, and the organic phase is dried with magnesium sulphate and concentrated under reduced pressure.

Workup

  1. temperatureunder reflux overnight
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is triturated thoroughly with acetone
  4. filtrationthe precipitated solid is filtered off with suction
  5. additionThe solid is added to 2 l of water
  6. stirringwith stirring with 31.8 g of sodium carbonate
  7. extractionextracted three times with a total of 1 l of ethyl acetate
  8. dry with materialthe organic phase is dried with magnesium sulphate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a1c64e84a1a4327a1f82e046818e9e1
Source dataset
uspto-grants-2004_12
Patent number
US06833364B1

Reaction notes

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