Hydrochloric Acid → 2-{4-[(Butyl{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino) methyl]-2-methylphenoxy}-2-methylpropanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-{4-[(butyl{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]-2-methylphenoxy}-2-methylpropanoate (45 mg, 0.085 mmol) in methanol (1.5 mL) and tetrahydrofuran (1.5 mL) was added 2M NaOH aq. (1 mL). The resulting mixture was heated to 70° C. for 1 h and then stirred at room temperature for 18 h, before heating to 70° C. for a further 4 h. The reaction mixture was allowed to attain room temperature and the solvents removed in vacuo. The residue was acidified with 2M HCl and extracted with EtOAc (2×10 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo. Purification by aminopropyl SPE (5 g) conditioning the cartridge, loading the compound and washing with methanol before eluting using 10% NH3 in methanol. Evaporation of the methanolic ammonia yielded a white solid, which was treated with 1 M HCl (5 mL) and then extracted into CH2Cl2 (20 mL). The organic extract was dried (Na2SO4) and the solvent removed in vacuo to afford the title compound as a colourless oil (19 mg).

Provenance & Evidence