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

HRID 346530Notes

Reaction equation

HRID 346530 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 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidate in methanol obtained from Example 5A 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. It is added to 2 l of water, 31.8 g of sodium carbonate are added while stirring, the mixture is extracted three times with a total of 1 l of ethyl acetate, and the organic phase is dried with magnesium sulphate and evaporated in vacuo.

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
  5. additionIt is added to 2 l of water, 31.8 g of sodium carbonate
  6. additionare added
  7. stirringwhile stirring
  8. extractionthe mixture is extracted three times with a total of 1 l of ethyl acetate
  9. dry with materialthe organic phase is dried with magnesium sulphate
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-97f2e585540341c28c33f72a2a16292c
Source dataset
uspto-grants-2007_02
Patent number
US07173037B2

Reaction notes

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