1,2-Dichloroethane → HCID 66677906, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-ethyl-5-(pyridin-2-yl)isoxazole-3-carboxylic acid, sodium salt (22 mg), HOBt (27.8 mg, 0.181 mmol), and diisopropylethylamine (0.070 mL, 0.403 mmol) in acetonitrile (1 mL) was added EDC (45.4 mg, 0.237 mmol) and tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate, Int. 1 (30.8 mg, 0.101 mmol). The reaction mixture was stirred at 80° C. for 4 h. and then concentrated under reduced pressure. The residue was diluted with ethyl acetate (3 mL), washed with a saturated aqueous solution of sodium bicarbonate, washed with water (1 mL), washed with brine (1 mL), and dried over anhydrous sodium sulfate. Concentration followed by purification by preparative HPLC [Prep HPLC: Column: PHENOMENEX® S10 30×100 mm; Gradient time: 10 min; Flow rate=40 ml/min; Solvent A=10% MeOH—90% Water—0.1% TFA; Solvent B=90% MeOH—10% water—0.1% TFA; Start % B=20; Final % B=100.] afforded tert-butyl 1-(4-(5-(4-ethyl-5-(pyridin-2-yl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate.

Provenance & Evidence