Hydrochloric Acid → HCID 89767871, compound

Participants

Reaction Steps

To a mixture of ethyl(6-((4-chloro-2-methylpyrimidin-5-yl)methoxy)-1-benzothiophen-3-yl)acetate (70 mg) in THF (3 mL) and EtOH (2 mL) was added 4N LiOH (0.186 mL) at room temperature. The mixture was stirred at room temperature for 5 h. The mixture was neutralized with 1N HCl at room temperature and concentrated in vacuo. Water and saturated aqueous NH4Cl were poured into the residue and extracted with EtOAc. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative HPLC (C18, water/CH3CN (including 0.1% TFA)). The fraction including Example 72 was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residual solid was recrystallized from EtOAc-hexane to give (6-((4-chloro-2-methylpyrimidin-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acid (Example 72, 18 mg). The fraction including Example 73 was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residual solid was recrystallized from EtOAc-hexane to give (6-((4-ethoxy-2-methylpyrimidin-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acid (Example 73, 12.8 mg).

Provenance & Evidence