Hydrochloric Acid → HCID 59146124, compound

HRID 1512962Notes

Reaction equation

HRID 1512962 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[C:24]([F:26])[CH:25]=3)[NH:22][C:21]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].Cl>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[C:24]([F:26])[CH:25]=3)[NH:22][C:21]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59146065HCID 59146065, compound

Product 1

HCID 59146124HCID 59146124, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of ethyl 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-7-fluoro-1H-indol-2-yl]propanoate (D164) (240 mg) in isopropanol (15 mL) was added 20% sodium hydroxide (509 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-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-7-fluoro-1H-indol-2-yl]propanoic acid (E112) (75.3 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.30 (6H, d), 2.65 (2H, t), 2.93 (2H, t), 4.8 (1H, m), 6.38 (1H, s), 7.36 (1H, d), 7.44 (1H, d), 8.01 (1H, s), 8.05 (1H, d), 8.11 (1H, s), 11.76 (1H, s), 12.20 (1H, s); δF (DMSO-d6, 376 MHz): −132.6; MS (ES): C22H19ClFN3O4 requires 443; found 444.2 (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-13ad419b37e04680ae610e2b51146873
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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