Trifluoroacetic acid → 1-[3-(Pyridin-4-yl)-1,2,4-oxadiazol-5-yl]methanamine

HRID 221342Notes

Reaction equation

HRID 221342 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][C:16]1[O:20][N:19]=[C:18]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[N:17]=1)(C)(C)C>C(Cl)Cl>[N:24]1[CH:23]=[CH:22][C:21]([C:18]2[N:17]=[C:16]([CH2:15][NH2:14])[O:20][N:19]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 56770463HCID 56770463, compound

Product 1

HCID 162277101-[3-(Pyridin-4-yl)-1,2,4-oxadiazol-5-yl]methanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (6.5 ml) was added to a solution of (3-pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl)carbamic acid tert-butyl ester (Preparation 8, 420 mg, 1.52 mmol in CH2Cl2 (10 ml) and the mixture stirred at rt for 2 h. The solvent was evaporated and the residue dissolved in EtOAc (100 ml). After washing with saturated aqueous Na2CO3 (25 ml), the aqueous phase was re-extracted with 5% MeOH in CH2Cl2 (7×25 ml) and the combined organic phases dried (MgSO4). The solvent was removed to afford the title compound: RT=0.25 min; m/z (ES+)=177.1 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in EtOAc (100 ml)
  3. washAfter washing with saturated aqueous Na2CO3 (25 ml)
  4. extractionthe aqueous phase was re-extracted with 5% MeOH in CH2Cl2 (7×25 ml)
  5. dry with materialthe combined organic phases dried (MgSO4)
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-be43608e5a7e454baafba28c2509aab6
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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