Reaction Steps
A mixture of compound 18 (0.58 g, 2 mmol) and CDI (0.34 g, 2.1 mmol) in THF (10 mL) was stirred at 60° C. for 6 h. The solvent was removed in vacuo, the residue was triturated with diethyl ether, and the resultant off-white solid was filtered and washed with diethyl ether to obtain compound 13. Yield: 68%, off-white solid, mp 244-245° C. IR (KBr, cm1) 3433, 3191 (CONH), 3037 (Ar—H), 2978 (Alph-H), 1713, 1689 (C=0), 1604, 1433 (C═C), 1244 (C—N), 1178 (C-0); 1H NMR (500 MHz, DMSO d6)g 1.39 (s, 9H, OC(CH3)3), 2.48 (br. s, 2H, CH2), 3.54 (m, 2H, CH2), 3.93 (br. s, 2H, CH2), 5.97 (br. s, 1H, CH), 6.86 (d, J=8.2 Hz, 1H, H-7), 6.95 (d, J=2.4 Hz, 1H, H-4), 6.99 (dd, J=2.4, 8.2 Hz, 1H, H-6), 10.60 (br. s, 2FI, NH). 13C NMR (125.7 MHz, DMSO d6) δ 26.84 (CH2), 28.28 (OC(CH3)3), 32.33 (CH), 42.80 (CH2), 79.08 (OC(CH3)3), 105.16 (CH), 108.52 (C-4), 117.67 (C-7), 129.20 (C-6), 130.04 (C-8), 133.28 (C-5/C-9), 134.81 (C-5/C-9), 154.73 (CO), 155.67 (CO). Anal. Calcd for C17H21N3O3: C, 64.74; H, 6.71; N, 13.32%. Found: C, 64.68; H, 6.76; N, 13.24%.
