HCID 178488374, compound → N-(7-hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide

Participants

Reaction Steps

N-(7-Methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (Step 5, 8.7 g, 27 mmol) in NMP (90 mL) was heated to 150° C. and Na2S (10.6 g, 135 mmol) was added portionwise. The reaction color briefly became blue-green, then changed back to yellow-brown. After stirring at this temperature for 1.5 h, the reaction was cooled to rt whereupon a yellow solid precipitated. The mixture was diluted with EtOAc (200 mL) and the solid collected by vacuum filtration. The solid was suspended in water (200 mL), the pH adjusted to ˜7 by the slow addition of aqueous 2N HCl and the mixture was stirred 2 h. The solid was collected via vacuum filtration and washed with water (50 mL) and finally with acetone (50 mL). High vacuum drying overnight gave the title compound (7.8 g, 93%): HPLC MS RT=0.34 min, MH+=308.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 4.25-4.31 (2H, m), 4.57-4.64 (2H, m), 7.45-7.49 (2H, m), 7.69-7.72 (1H, m), 7.92 (1H, dd), 8.78 (1H, dt), 8.97 (1H, dd), 9.49 (1H, d).

Provenance & Evidence