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

HRID 351660Notes

Reaction equation

HRID 351660 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]([NH2:27])=[NH:17])=[N:6]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

The above solution of methyl (2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidate from Example 24A in methanol 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 the mixture is stirred under reflux overnight. The solvent is evaporated off under reduced pressure, the residue is triturated well with acetone and the precipitated solid is filtered off with suction. The product is added to 2 l of water, the mixture is 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 off under reduced pressure
  3. customthe residue is triturated well with acetone
  4. filtrationthe precipitated solid is filtered off with suction
  5. additionThe product 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-18ddfea9464049ab9ae8c46757087efe
Source dataset
uspto-grants-2004_06
Patent number
US06743798B1

Reaction notes

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