Hydrochloric Acid → HCID 59146099, compound

HRID 1512964Notes

Reaction equation

HRID 1512964 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]=[N: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]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59146170HCID 59146170, compound

Product 1

HCID 59146099HCID 59146099, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of ethyl 3-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-7-fluoro-1H-indol-2-yl]propanoate (D166) (720 mg) in isopropanol (20 mL) was added 20% sodium hydroxide (1.52 g) 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 and the filtrate was purified by Mass Directed Auto Prep to afford 3-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-7-fluoro-1H-indol-2-yl]propanoic acid (E114) (41 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.32 (6H, s), 2.65 (2H, t), 2.94 (2H, t), 5.38 (1H, m), 6.38 (1H, s), 7.43 (1H, d), 8.01 (1H, s), 8.48 (1H, d), 8.85 (1H, d), 11.78 (1H, s); δF (DMSO-d6, 376 MHz): −132.6; MS (ES): C21H18ClFN4O4 requires 444. found 445.2 (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-eca16e485100469aaa9bbba3cf5d9b4e
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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