Acetic Acid → 1-(4-(5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid

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Reaction Steps

To a solution of 4-(5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde (700 mg, 1.821 mmol) in MeOH (12 mL) and 1,2-dichloroethane (3 mL) was added 0.1 mL of acetic acid and azetidine-3-carboxylic acid (203 mg, 2.0 mmol). The mixture was allowed to stir at room temperature for 40 min. and then sodium triacetoxyborohydride (618 mg, 2.91 mmol) was added. The mixture was allowed to stir at room temperature for 5 hours, then was filtered to afford a white solid that was washed with water (1 mL) and MeOH (3×1 mL). The solid was dried under vacuum to give 1-(4-(5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid (480 mg, 1.02 mmol). The compound had an HPLC retention time=6.91 min. −Column: Low pH Col-1: Sunfire C18 3.5 um, 4.6×150 mm; Start % B=10; 12 Min. 100%; 15 Min. 100%; Flow Rate=2 mL/min; Wavelength1=220; Wavelength2=254; Solvent Pair=TFA-MeCN/H2O; Solvent A=0.05% TFA in H2O:MeCN (95:5); Solvent B=0.05% TFA in H2O:MeCN (5:95); Column 1=LOW pH-Parallel HPLC; At 220 nm LC/MS M+1=470.1 1H NMR (500 MHz, MeOD) δ ppm 3.41 (dt, J=8.8 Hz, 7.7 Hz, 1H), 4.12-4.18 (m, 4H), 4.38 (s, 2H), 7.57-7.66 (m, 7H), 8.23 (d, J=8.3 Hz, 2H), 8.50 (s, 1H).

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