Water → HCID 69183112, compound

Participants

Reaction Steps

A mixture of 6-(2-morpholinoethylamino)-4-(3-nitrophenylamino)-1,7-naphthyridine-3-carbonitrile (120 mg, 0.29 mmol, 1 eq) and SnCl2.2H2O (348 mg, 1.54 mmol, 5.3 eq) in ethyl alcohol (12 mL) was heated to reflux for 2.5 hr. After cooling to room temperature, water (10 mL) was added followed by sodium bicarbonate (500 mg). The mixture was stirred at room temperature for 1 hr. Ethyl acetate extraction followed by column chromatography (3-5% methyl alcohol in dichloromethane) yield 43 mg product (39% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 2.40-2.48 (m, 4 H) 2.53-2.60 (m, 2 H) 3.34-3.40 (m, 2 H) 3.54-3.63 (m, 4 H) 5.18-5.27 (m, 2 H) 6.39-6.47 (m, 3 H) 6.57 (s, 1 H) 7.01-7.08 (m, 2 H) 8.22 (s, 1 H) 8.81 (s, 1 H) 9.43 (s, 1 H).

Provenance & Evidence