Hydrochloric Acid → HCID 59146070, compound

HRID 1512963Notes

Reaction equation

HRID 1512963 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[C:25]([F:27])[CH:26]=3)[NH:23][C:22]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[CH:21]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+].Cl>C(O)(C)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[C:25]([F:27])[CH:26]=3)[NH:23][C:22]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:21]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59146030HCID 59146030, compound

Product 1

HCID 59146070HCID 59146070, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-7-fluoro-1H-indol-2-yl]propanoate (D165) (310 mg) in isopropanol (20 mL) was added 20% sodium hydroxide (670 mg) solution. Then the reaction mixture was stirred at room temperature overnight. The mixture was acidified with HCl (2 M) to pH 4. The solvent of the reaction was removed by evaporation. The residue was dissolved in DMF (5 mL), the precipitation was filtered then the filtrate was purified by Mass Directed Auto Prep to afford 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-7-fluoro-1H-indol-2-yl]propanoic acid (E113) (54.6 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.38 (6H, d), 2.70 (2H, t), 2.99 (2H, t), 4.97 (1H, m), 6.44 (1H, s), 7.49 (1H, d), 7.54 (1H, d), 8.07 (1H, s), 8.39 (1H, dd), 8.50 (1H, d), 11.82 (1H, s). δF (DMSO-d6, 376 MHz): −132.6; MS (ES): C23H19FN4O4 requires 434; found 435.2 (M+H+).

Workup

  1. customThe solvent of the reaction was removed by evaporation
  2. dissolutionThe residue was dissolved in DMF (5 mL)
  3. customthe precipitation
  4. filtrationwas filtered
  5. customthe filtrate was purified by Mass Directed Auto Prep

Sources & evidence

ORD record
ord-992ac866d7fd4709a9ca7582a45e3dd6
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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