1,1-Dimethylethyl 3-[5-(5-{3-cyano-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate → 3-[5-(5-{3-Cyano-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoic acid

HRID 2192536Notes

Reaction equation

HRID 2192536 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:21]=3[CH:22]=[CH:23][N:24]=[C:25]4[CH2:30][CH2:31][C:32]([O:34]C(C)(C)C)=[O:33])[N:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12])#[N:2]>Cl.O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:21]=3[CH:22]=[CH:23][N:24]=[C:25]4[CH2:30][CH2:31][C:32]([OH:34])=[O:33])[N:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([F:13])([F:14])[F:12])#[N:2]

Participants

4

Reactant 1

HCID 581498841,1-Dimethylethyl 3-[5-(5-{3-cyano-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate

Product 1

HCID 444766763-[5-(5-{3-Cyano-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoic acidYield 85.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl 3-[5-(5-{3-cyano-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate (D49; 164 mg, 0.313 mmol) was stirred in 4M HCl in dioxane (3 ml) at room temperature for 2.5 hrs. The solvent was removed under vacuum and the residue was triturated under diethyl ether. Filtration provided a solid that was dried in a vacuum oven to give the title compound as a white solid (125 mg).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was triturated under diethyl ether
  3. filtrationFiltration
  4. customprovided a solid
  5. customthat was dried in a vacuum oven

Sources & evidence

ORD record
ord-1b7cb7f1d19c4b5db468edb3667f9889
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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