Diisopropylethylamine → HCID 178522808, compound

Participants

Reaction Conditions

Reaction Steps

Combined ethyl 3-(dimethylamino)-2-(pyridin-4-yl)acrylate (40.0 mg, 0.182 mmol) and N-benzyl-6-hydrazinylnicotinamide (33.8 mg, 0.140 mmol) in 2-propanol (0.698 mL) and stirred for 18 hours at room temperature. Hunig's base (0.219 mL, 1.257 mmol) was then added and the reaction was stirred for 24 hours at 50° C. The reaction mixture was then purified by preparative HPLC (SunFire™ C18, 5 μm, ID 30 mm×75 mm) eluting with ACN (with 0.035% TFA) in water (with 0.05% TFA) to give the title compound (18.5 mg, 35.7%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.58 (d, J=5.8 Hz, 2H) 7.33 (dq, J=8.5, 4.3 Hz, 1H) 7.37-7.45 (m, 4H) 8.28 (d, J=6.3 Hz, 2H) 8.45 (d, J=7.1 Hz, 2H) 8.49-8.58 (m, 2H) 8.63 (s, 1H) 8.99 (s, 1H) 9.33 (t, J=5.9 Hz, 1H). MS m/z [M+H]+ 372.4.

Provenance & Evidence