N-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide → HCID 178522494, compound

Participants

Reaction Conditions

Reaction Steps

N-[7-Methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]nicotinamide (Step 6, 1.0 g, 2.15 mmol) in NMP (20 mL) was heated to 100° C. and Na2S (0.84 g, 10.76 mmol) was added portionwise. The reaction was heated to 160° C. for 10 min and cooled to rt and concentrated under reduced pressure. The resulting slurry was diluted with water (100 mL) and the pH adjusted to 7 by the slow addition of aqueous 1N HCl and the mixture was stirred 2 h. The solid was collected via vacuum filtration and washed with water (50 mL) and finally triturated with CH2Cl2/heptane (10 mL). High vacuum drying overnight gave the title compound (0.49 g, 51%): HPLC MS RT=0.21 min, MH+=451; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.14-2.26 (2H, m), 3.03-3.17 (2H, m), 3.32-3.54 (4H, m), 3.60-3.72 (2H, m), 3.95-4.05 (2H, m), 4.18-4.35 (4H, m), 4.51-4.64 (2H, m), 7.38 (1H, d), 7.68 (1H, dd), 7.82 (1H, d), 8.63 (1H), 8.84 (1H, dd), 9.42 (1H, s), 13.39 (1H, s).

Provenance & Evidence