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

HRID 1670301Notes

Reaction equation

HRID 1670301 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-e5ecf470d9584b09b020e63669641102
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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