Trifluoroacetic acid → 3-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)benzoic Acid

HRID 450635Notes

Reaction equation

HRID 450635 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=3)[C:15]([O:17]C(C)(C)C)=[O:16])[O:9][N:8]=2)[CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=3)[C:15]([OH:17])=[O:16])[O:9][N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67026129HCID 67026129, compound

Product 1

HCID 629258423-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 45 (180 mg, 0.56 mmol) in methylene chloride (5 mL) was stirred with trifluoroacetic acid (1 mL) at room temperature for 4 hours. It was then concentrated and the residue was stirred in water (15 mL) for 1 hour. The precipitate was collected by filtration and dried to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.66 (ddd, J=7.9, 4.8, 0.8 Hz, 1 H), 7.83 (t, J=7.5 Hz, 1 H), 8.28 (ddd, J=8.0, 1.5, 1.2 Hz, 1 H), 8.42-8.51 (m, 2 H), 8.70 (t, J=1.6 Hz, 1 H), 8.83 (dd, J=5.0, 1.8 Hz, 1 H), 9.28 (dd, J=2.2, 1.0 Hz, 1 H) ppm; MS (DCI/NH3) m/z 268 (M+H)+.

Workup

  1. concentrationIt was then concentrated
  2. filtrationThe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-2faa390745e6446fae99a3c294e13ee0
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Reaction notes

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