Ethanol → 1H-Pyrazolo[3,4-b]pyridine-3-carboximidamide, 5-fluoro-1-[(2-fluorophenyl)methyl]-, hydrochloride (1:1)

HRID 1747261Notes

Reaction equation

HRID 1747261 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)C.C[O-].[Na+].[Cl-:27].[NH4+:28]>CO>[ClH:27].[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11](=[NH:28])[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 702EthanolHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 568467435-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

Product 1

HCID 866861511H-Pyrazolo[3,4-b]pyridine-3-carboximidamide, 5-fluoro-1-[(2-fluorophenyl)methyl]-, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

406.0 g (1.50 mol) of the compound from Example 8 were suspended in 2.08 1 of ethanol. Subsequently, 54.1 g (0.30 mol) of sodium methoxide in methanol (30%) were added and the mixture was stirred at room temperature overnight. 88.4 g (1.65 mol) of ammonium chloride were added, and the mixture was heated to 65° C. and stirred at 65° C. for 3.5 h. The solvents were distilled off and the residue was stirred with 1.6 1 of ethyl acetate overnight. The precipitated solids were filtered off with suction, washed twice with 140 ml each time of ethyl acetate and dried in a vacuum drying cabinet at 50° C. under a gentle nitrogen stream. This gave 441.4 g (90.7% of theory) of the title compound.

Workup

  1. temperaturethe mixture was heated to 65° C.
  2. stirringstirred at 65° C. for 3.5 h
  3. distillationThe solvents were distilled off
  4. stirringthe residue was stirred with 1.6 1 of ethyl acetate overnight
  5. filtrationThe precipitated solids were filtered off with suction
  6. washwashed twice with 140 ml each time of ethyl acetate
  7. customdried in a vacuum
  8. customdrying cabinet at 50° C. under a gentle nitrogen

Sources & evidence

ORD record
ord-2fab4de1e3ff45b7b65cd3d6e1b15742
Source dataset
uspto-grants-2015_10
Patent number
US09150573B2

Reaction notes

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