Hydrochloric Acid → 4-(4-Amino-3-fluorophenoxy)pyridin-2-amine

HRID 2374050Notes

Reaction equation

HRID 2374050 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(=O)C(C)(C)C)=[C:11]([F:22])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.Cl>CO>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=2)=[CH:10][C:11]=1[F:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59852964N-(4-(2-aminopyridin-4-yloxy)-2-fluorophenyl)pivalamide

Product 1

HCID 71470884-(4-Amino-3-fluorophenoxy)pyridin-2-amineYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(4-(2-aminopyridin-4-yloxy)-2-fluorophenyl)pivalamide (70 mg, 0.23 mmol) in 3 mL of MeOH was added 2 mL of 6 N HCl. The mixture was then heated at reflux for 48 h. After cooling down, the solvent was removed under reduced pressure and the residue was purified by solid extraction (Waters Oasis®MCX extraction cartridge) to give 4-(4-amino-3-fluorophenoxy)pyridin-2-amine (27 mg, 54% yield). MS(ESI+): m/z 220.21 (M+H)+.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 48 h
  3. temperatureAfter cooling down
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by solid extraction (Waters Oasis®MCX extraction cartridge)

Sources & evidence

ORD record
ord-e0223b378c7144e4a5db7ae971dc7c24
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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