Trifluoroacetic acid → 4-(5-Piperidin-4-yl-1,2,4-oxadiazol-3-yl)pyridine

HRID 221357Notes

Reaction equation

HRID 221357 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[N:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[N:22]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57954381HCID 57954381, compound

Product 1

HCID 27611434-(5-Piperidin-4-yl-1,2,4-oxadiazol-3-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 ml) was added to a stirred solution of 4-(3-pyridin-4-yl-[1,2,4]oxadiazol-5-yl)piperidine-1-carboxylic acid tert-butyl ester (Example 2, 1.64 g, 4.96 mmol) in CH2Cl2 (35 ml). After 2.5 h at rt, the solvent was evaporated under reduced pressure. The residual solid was suspended in EtOAc (150 ml) and washed with saturated aqueous Na2CO3 (20 ml). The aqueous was separated and extracted with EtOAc (3×30 ml). The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure to afford the title compound: RT=3.48 min, m/z (ES+)=231.2 [M+H]+.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. washwashed with saturated aqueous Na2CO3 (20 ml)
  3. customThe aqueous was separated
  4. extractionextracted with EtOAc (3×30 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-19e6641f26994c159f56e6339993d2d0
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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