Ammonia → HCID 71483937, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added (Z)-3-(2-(((1R,2R)-2-(((S)-1-(4-cyanophenyl)piperidin-3-yl)amino)cyclohexyl)amino)pyridin-4-yl)acrylic acid (35 mg, 0.063 mmol), THF (0.8 mL) and Et3N (0.026 mL, 0.188 mmol). The reaction was cooled to 0° C. Then isobutyl chloroformate (9.04 μl, 0.069 mmol) was added to the reaction and the reaction was stirred at 0° C. for 15 mins before ammonia (0.045 mL, 0.313 mmol) in methanol was added to the reaction. The reaction was stirred at 0° C. for 30 mins. The reaction was concentrated and purified using RP prep-HPLC. The desired fraction was concentrated to give (Z)-3-(2-(((1R,2R)-2-(((S)-1-(4-cyanophenyl)piperidin-3-yl)amino)cyclohexyl)amino)pyridin-4-yl)acrylamide (8 mg, 0.014 mmol, 21.98% yield) as a light brown film. Anal. Calcd. for C26H32N6O m/z 444.3, found: 445.5 (M+H)+; 1H NMR (400 MHz, METHANOL-D4) δ ppm 7.87 (d, J=6.6 Hz, 1H), 7.47 (d, J=8.8 Hz, 2H), 7.00-6.89 (m, 3H), 6.84 (br. s., 1H), 6.67 (d, J=12.6 Hz, 1H), 6.35 (d, J=12.6 Hz, 1H), 3.88-3.67 (m, 2H), 3.63-3.52 (m, 1H), 3.50-3.42 (m, 1H), 3.40-3.33 (m, 2H), 3.18-3.08 (m, 1H), 2.34 (d, J=12.6 Hz, 1H), 2.14 (dd, J=9.6, 3.0 Hz, 2H), 1.91-1.72 (m, 4H), 1.66-1.53 (m, 1H), 1.52-1.40 (m, 3H), 1.33-1.26 (m, 1H)

Provenance & Evidence