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

HRID 1505453Notes

Reaction equation

HRID 1505453 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 8A) were added to 2.22 g (41.07 mmol) of sodium methoxide in methanol (270 ml), and the mixture was stirred at RT for 2 h. 2.64 g (49.29 mmol) of ammonium chloride and acetic acid (9.17 ml) were added, and the mixture was heated at reflux overnight. The mixture was then concentrated to dryness, and the residue was taken up in water (100 ml) and ethyl acetate (100 ml) and adjusted to pH 10 with 2 N aqueous sodium hydroxide solution. The mixture was stirred at RT for about 1 h. The resulting suspension was filtered off with suction and washed with ethyl acetate (100 ml), water (100 ml) and once more with ethyl acetate (100 ml). The residue was dried over phosphorus pentoxide under high vacuum.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was then concentrated to dryness
  4. stirringThe mixture was stirred at RT for about 1 h
  5. filtrationThe resulting suspension was filtered off with suction
  6. washwashed with ethyl acetate (100 ml), water (100 ml) and once more with ethyl acetate (100 ml)
  7. dry with materialThe residue was dried over phosphorus pentoxide under high vacuum

Sources & evidence

ORD record
ord-9a9307c1231b48d282511a3fdf14198a
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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