Trifluoroacetic acid → 1-(4-(5-(4-Propyl-5-(pyridin-2-yl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid trifluoroacetic acid salt

Participants

Reaction Steps

A solution of tert-butyl 1-(4-(5-(4-propyl-5-(pyridin-2-yl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate in dichloromethane (0.5 mL) and trifluoroacetic acid (0.5 mL) was stirred at room temperature for 30 minutes. The reaction mixture was concentrated to yield 1-(4-(5-(4-propyl-5-(pyridin-2-yl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid trifluoroacetic acid salt (17.4 mg). The compound had an HPLC retention time=7.75 min.—Column: Xbridge Ph 3.5 u 4.6×150 mm; Gradient time: 12 min, hold for 3 minutes; Flow rate=2 ml/min; Solvent A=5% MeCN—95% Water—0.05% TFA; Solvent B=95% MeCN—5% water—0.05% TFA; Start % B=10; Final % B=100. LC-MS: M+1=446+. 1H NMR (500 MHz, MeOD) δ ppm 1.04 (t, 3H), 1.73-1.83 (m, 2H), 3.34-3.40 (m, 2H), 3.73 (t, J=8.25 Hz, 1H), 4.39 (d, J=7.42 Hz, 4H), 4.54 (s, 2H), 7.51 (ddd, J=6.74, 4.67, 2.06 Hz, 1H), 7.70 (d, J=8.25 Hz, 2H), 7.98-8.06 (m, 2H), 8.30 (d, J=8.25 Hz, 2H), and 8.78 (d, J=4.40 Hz, 1H).

Provenance & Evidence