To a solution of 4-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]piperidine (D122) (108 mg, 0.244 mmol) and ethyl 4-bromobutanoate (95 mg, 0.489 mmol) in N,N-Dimethylformamide (DMF) (8 mL) was added K2CO3 (223 mg, 1.614 mmol). This solution was sealed and stirred for overnight at room temperature. To the above solution was added Isopropanol (10.00 mL) and Water (2 mL) and sodium hydroxide (0.5 mL, 3.05 mmol). The solution was sealed and stirred for 5 h at 40° C. The reaction was neutrolized by AcOH, dried and purified by Mass Directed AutoPrep to afford 4-{4-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]-1-piperidinyl}butanoic acid (E102) (62 mg) as a TFA salt.
