Diisopropylethylamine → (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)-N-((2-methylpyrimidin-5-yl)methyl)acrylamide

関与物質

反応条件

反応手順

In a 25 mL 3N round-bottomed flask equipped with nitrogen inlet, (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylic acid (4) (0.1 g, 1.0 eq.) was charged along with dichloromethane (5.0 mL, 50 V) and ethyl acetate (5.0 mL, 50 V). The reaction mixture was cooled to 0° C. and then added T3P (50% in ethyl acetate) (0.214 g, 1.2 eq.) followed by DIPEA (0.073 g, 2.0 eq.) and (2-methylpyrimidin-5-yl)methanamine (0.038 g, 1.1 eq.). The clear reaction mixture was stirred at 0° C. for 30 min. The progress of the reaction was followed by TLC analysis on silica gel with 10% Methanol in dichloromethane as mobile phase and visualization with UV. Reaction mixture was quenched in 30 mL ice-water slurry. Organic layer was separated and aqueous layer was extracted with dichloromethane (2×20 mL) to ensure complete extraction. The organic layer was washed with brine solution and dried over anhydrous Na2SO4 and concentrated by rotary evaporation under reduced pressure (35° C., 20 mm Hg) to afford 0.129 g of crude compound. (cis: 81.98%; trans: not detected; unreacted SM: 13.95%).

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