Acetic Acid → 5-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide acetate

HRID 536481Notes

Reaction equation

HRID 536481 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]#[N:12])=[N:9][N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:5]2=[N:6][CH:7]=1.C[O-].[Na+].[Cl-].[NH4+:25].[C:26]([OH:29])(=[O:28])[CH3:27]>CO>[C:26]([OH:29])(=[O:28])[CH3:27].[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11](=[NH:25])[NH2:12])=[N:9][N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 568467435-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

Product 1

HCID 666833225-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.1 g (41.07 mmol) of 5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile (example 10A) was added to 2.22 g (41.07 mmol) of sodium methanolate in methanol (270 ml) and stirred for 2 h at RT. Then 2.64 g (49.29 mmol) of ammonium chloride and acetic acid (9.17 ml) were added and it was heated under reflux overnight. Then the reaction mixture was evaporated to dryness and the residue was taken up in water (100 ml) and ethyl acetate (100 ml) and was adjusted to pH 10 with 2N sodium hydroxide solution. It was stirred vigorously for approx. 1 h at RT. The suspension obtained was filtered with suction and was washed with ethyl acetate (100 ml), water (100 ml) and again with ethyl acetate (100 ml). The residue is dried over phosphorus pentoxide under high vacuum.

Workup

  1. temperatureit was heated
  2. temperatureunder reflux overnight
  3. customThen the reaction mixture was evaporated to dryness
  4. stirringIt was stirred vigorously for approx. 1 h at RT
  5. customThe suspension obtained
  6. filtrationwas filtered with suction
  7. washwas washed with ethyl acetate (100 ml), water (100 ml) and again with ethyl acetate (100 ml)
  8. dry with materialThe residue is dried over phosphorus pentoxide under high vacuum

Sources & evidence

ORD record
ord-5775f72badda40819b74a54ab058c7f6
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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