Methanol → 3-(5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoic acid

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Reaction Conditions

Reaction Steps

D3 (38 mg) was dissolved in 2M aqueous NaOH (0.5 ml) and MeOH (0.5 ml) then stirred at RT overnight. LCMS analysis showed 41% product so the reaction mixture was heated to 50° C. and stirred over the weekend. LCMS showed the reaction to be complete. The reaction mixture was evaporated then partitioned between H2O and DCM. The organic layer was extracted with H2O. The combined aqueous extracts were acidified to pH=1 and extracted with DCM. These DCM extracts were dried over MgSO4, filtered and evaporated to give the crude product MF105672-149A1 (30 mg). The crude product was purified on a silica cartridge (12+S), eluting with a 0 to 10% mixture of MeOH in DCM to give the purified product. This was dissolved in CHCl3 and evaporated to give the title compound (3 mg) as a white solid. δH (CDCl3, 400 MHz): 2.92 (2H, t), 4.50 (2H, t), 6.51 (1H, d), 7.24 (1H, d), 7.40-7.53 (6H, m), 7.90 (1H, s), 8.00 (1H, d), 8.45 (1H, s). MS (ES+): C24H16F3N3O3S requires 483; found 484 (MH+).

Provenance & Evidence