Trifluoroacetic acid → HCID 58443335, compound

HRID 400776Notes

Reaction equation

HRID 400776 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])[CH:17]=[CH:16]4)[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH3:36].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH2:22][C:23]([OH:25])=[O:24])[CH:17]=[CH:16]4)[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68653755HCID 68653755, compound

Product 1

HCID 58443335HCID 58443335, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl {5-[5-(2,2′-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-1H-indol-1-yl}acetate obtained in step 1 was taken up in DCM (2 mL) and TFA (0.50 ml) was added at 0° C. and allowed to return to RT. After 6 hours, solvents were evaporated under vacuum to give a light yellow oil. Purification by silica column chromatography (c-Hexane/EtOAc, 85/15 then 50/50+1% AcOH) gave a colourless oil which was triturated in a mixture of Et2O and n-Hexane to give the title compound as an off-white solid. HPLC (Method A) Rt 5.41 min (Purity: 97.1%). LC/MS (method A): 422.0 (M−H)−.

Workup

  1. customto return to RT
  2. customsolvents were evaporated under vacuum
  3. customto give a light yellow oil
  4. customPurification by silica column chromatography (c-Hexane/EtOAc, 85/15
  5. custom50/50+1% AcOH) gave a colourless oil which
  6. customwas triturated in a mixture of Et2O and n-Hexane

Sources & evidence

ORD record
ord-e147f9d75c094826817279c3d4193e2d
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

Loading…