Hydrochloric Acid → 4-Chloro-3-(3-{[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]methyl}-1,2,4-oxadiazol-5-yl)benzoic acid

HRID 913680Notes

Reaction equation

HRID 913680 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[C:12]1[O:16][N:15]=[C:14]([CH2:17][N:18]2[C:26]3[C:21](=[C:22]([C:29]([F:32])([F:31])[F:30])[C:23]([C:27]#[N:28])=[CH:24][CH:25]=3)[CH:20]=[C:19]2[CH2:33][CH2:34][CH3:35])[N:13]=1.O[Li].O.O.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:12]1[O:16][N:15]=[C:14]([CH2:17][N:18]2[C:26]3[C:21](=[C:22]([C:29]([F:31])([F:30])[F:32])[C:23]([C:27]#[N:28])=[CH:24][CH:25]=3)[CH:20]=[C:19]2[CH2:33][CH2:34][CH3:35])[N:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57800414Methyl 4-chloro-3-(3-{[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]methyl}-1,2,4-oxadiazol-5-yl)benzoate

Product 1

HCID 578004394-Chloro-3-(3-{[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]methyl}-1,2,4-oxadiazol-5-yl)benzoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 4-chloro-3-(3-{[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]methyl}-1,2,4-oxadiazol-5-yl)benzoate (Example 293) (0.190 g, 0.378 mmol) in 1,4-dioxane (70 mL) was added LiOH—H2O (0.063 g, 1.50 mmol) and water (30 mL). The mixture was stirred at rt for 17 h followed by cooling to 0-5° C. The solution was made acidic using concentrated HCl, extracted into Et2O, dried (MgSO4) and concentrated to afford a pure solid (0.131 g, 71% yield): MS (ES) m/z 488 (M+).

Workup

  1. temperatureby cooling to 0-5° C
  2. extractionextracted into Et2O
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d4ba7519e244d128853306ea2aaffc1
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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