Trifluoroacetic acid → 5-Fluoro-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-3-amine

HRID 524960Notes

Reaction equation

HRID 524960 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[C:10]([CH:23]2[CH2:28][CH2:27][N:26]([CH:29]3[CH2:32][O:31][CH2:30]3)[CH2:25][CH2:24]2)=[C:11]([NH:15]C(=O)OC(C)(C)C)[CH:12]=[N:13][CH:14]=1>C(Cl)Cl>[F:8][C:9]1[C:10]([CH:23]2[CH2:28][CH2:27][N:26]([CH:29]3[CH2:32][O:31][CH2:30]3)[CH2:25][CH2:24]2)=[C:11]([NH2:15])[CH:12]=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86721015Tert-butyl (5-fluoro-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-3-yl)carbamate

Product 1

HCID 867210165-Fluoro-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-3-amineYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL, 12.98 mmol) was added to a stirred solution of tert-butyl N-[5-fluoro-4-[1-(oxetan-3-yl)-4-piperidyl]-3-pyridyl]carbamate (174 mg, 0.4951 mmol) in DCM (5 mL) and the reaction stirred at ambient temperature for 4 hours. The solvent was removed in vacuo and the residue azeotroped with DCM (×2) and ether (×2). The residue was passed through a 5 g SCX-2 cartridge and washed with MeOH/DCM mixtures. The product was eluted by washing the cartridge with 2M NH3 in MeOH/DCM mixtures and concentrated in vacuo to give 5-fluoro-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-3-amine as a yellow oil (109 mg, 88% Yield). MS (ES+) 252.1.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with DCM (×2) and ether (×2)
  3. washwashed with MeOH/DCM
  4. washThe product was eluted
  5. washby washing the cartridge with 2M NH3 in MeOH/DCM mixtures
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce31e3cddb2d4c39950fced307e44aef
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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