4-(Piperidin-4-ylamino)benzoic Acid tert-Butyl Ester → 4-[1-(6,7-Dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl) piperidin-4-ylamino]benzoic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

4-(Piperidin-4-ylamino)benzoic Acid tert-Butyl Ester (49) (0.47 mmol) was added to a solution of 2-chloro-4,6,7-trimethoxy-quinazoline (0.1 g, 0.39 mmol) in n-pentanol (5 mL) at 25° C. The mixture was stirred at 120° C. for 12 h. The reaction mixture was then cooled to room temperature and the desired product was filtered and rinsed with acetone to give 0.06 g (32%) of (15): TLC (Rf =0.30; 5% CH3OH/CH2Cl2); 1H NMR (DMSO) δ 11.24 (s, 1H), 7.61 (d, 2H, J=8.4), 7.26 (s, 1H), 6.76 (s, 1H), 6.60 (d, 2H, J=8.7), 6.36 (d, 1H, J=7.8), 4.24 (d, 2H, J=13.6), 3.83 (s, 3H), 3.78 (s, 3H), 3.60 (m, 1H), 3.09 (m, 2H), 1.94 (d, 2H, J=10.4), 1.48 (s, 9H), 1.40 (m, 2H) 13C NMR (DMSO) δ 165.2, 162.4, 154.9, 151.4, 150.1, 146.7, 145.6, 130.9, 117.6, 111.2, 109.2, 106.0, 105.3, 78.9, 55.7, 55.5, 48.4, 43.9, 30.9, 28.0; HRMS (FAB) m/z 481.2444 (M+H)+ (C26H32N4O5 requires 481.2443); Anal. (C26H32N4O5 ·1/2HCl) C, H, N.

Provenance & Evidence