Ammonium Acetate → HCID 178513844, compound

HRID 1463230Notes

Reaction equation

HRID 1463230 reaction equation
[F:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([C:11]([O:13]C(C)(C)C)=O)[C:5]2=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:22]>FC(F)(F)C(O)=O>[F:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([C:11]([NH2:22])=[O:13])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 178450870HCID 178450870, compound

Product 1

HCID 178513844HCID 178513844, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

t-Butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (8.90 g, 37.5 mmole) was dissolved in 30 mL of trifluoroacetic acid and allowed to stand undisturbed for 2 hours. The solvent was then evaporated and the residue was dissolved in 30 mL of DMF. N,N'-Carbonyldiimidazole (7.0 g, 43.2 mmol) was added and the reaction mixture was stirred overnight. Ammonium acetate (8.7 g, 113 mmol) was then added to the resulting suspendion and stirring was continued for 4 hours. The solvent was evaporated under high vacuum and the residue was triturated well with H2O to give 6.02 g (89%) of product after drying. An analytical sample was obtained by recrystallization from HOAc, mp 295° C. (dec).

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe residue was dissolved in 30 mL of DMF
  3. stirringstirring
  4. waitwas continued for 4 hours
  5. customThe solvent was evaporated under high vacuum
  6. customthe residue was triturated well with H2O

Sources & evidence

ORD record
ord-600a837bffa34c74a0c4966c53af5ea1
Source dataset
uspto-grants-1994_04
Patent number
US05300498

Reaction notes

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