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

HRID 2404950Notes

Reaction equation

HRID 2404950 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 2.081 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 1.61 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 1.61 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-d4bc6831d7124a579a403c40a4800ba9
Source dataset
uspto-grants-2014_08
Patent number
US08802847B2

Reaction notes

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