A mixture of 5-chloro-2-(3-(4-fluorophenoxy)azetidin-1-yl)nicotinic acid (D102) (75 mg, 0.232 mmol) 1-Hydroxybenzotriazole hydrate (31.34 mg, 0.232 mmol) and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (66.8 mg, 0.35 mmol) in dichloromethane (3 ml) was stirred 1 h at room temperature. A solution (S)-methyl 4-(1-aminoethyl)benzoate (D3) (50 mg, 0.232 mmol) and triethylamine (0.03 ml, 0.232 mmol) in dichloromethane (1 ml) was added and the resulting mixture was stirred overnight at room temperature. NaHCO3 sat. sol. (5 ml) was added and the mixture was extracted with dichloromethane (3×10 ml). Collected organics, after solvent evaporation were purified by SPE-Si (10 g) eluting with a mixture Cyclohexane/ethylacetate from 95/05 to 60/40. Collected fractions, after solvent evaporation, afforded the title compound (D146) (100 mg).
