Design, Synthesis, and Biological Activity Analysis of Novel Quinazolinyl Ether Derivatives Containing Piperidinamide Structure
Characterization data of the intermediates and target compounds 2 Original spectral files of the intermediates and target compounds13 N-(2-hydroxyphenyl)-1-(quinazolin-4-yl)piperidine-4-carboxamide (II):red solid,Yield: 47%, mp 256-257 °C. 1 H NMR (400 MHz, DMSO-d6) δ: 9.80 (s, 1H), 9.29 (s, 1H), 8.63 (s, 1H), 8.00 (d, J = 8.4 Hz, 1H), 7.81-7.80(m, 2H), 7.75 (d, J = 8.0 Hz, 1H), 7.58-7.51(m, 1H), 6.95-6.92(m, 1H), 6.86 (d, J = 8.1 Hz, 1H), 6.78-6.74(m, 1H), 4.34 (d, J = 14.3 Hz, 2H), 3.20 (t, J = 12.8 Hz, 2H), 2.95-2.86(m, 1H), 1.95 (d, J = 12.1 Hz, 2H), 1.91-1.81(m, 2H). 13C NMR (100 MHz, DMSO-d6) δ: 173.6, 164.0, 153.8, 151.4,148.0, 132.8, 128.1, 126.4,125.7, 125.5, 124.7, 122.4,119.1, 116.0, 115.8, 49.1, 42.3, 28.6.ESI-HRMS m/z: [M -H] -calcd for C20H19N4O2: 347.1503; found: 347.1514. N-[2-[(2-cyanobenzyl)oxy]phenyl]-1-(quinazolin-4-yl)piperidine-4-carboxamide(III-1): White solid, mp 219-220 °C, yield: 43.6%. 1 H NMR (400 MHz, DMSO-d6) δ: 9.07 (s, 1H), 8.63 (s, 1H), 7.97 (d, J = 8.2 Hz, 1H), 7.90 (d, J = 6.5 Hz, 1H), 7.86 (d, J = 6.2 Hz, 1H), 7. 81-7.79 (m, 2H), 7.78 (s, 1H), 7.76-7.72(m, 1H), 7.57-7.52(m, 2H), 7.17-7.07(m, 2H), 6.98-6.94(m, 1H), 5.35 (s, 2H), 4.30 (d, J = 13.3Hz, 2H), 3.20 (t, J = 11.1 Hz, 2H), 2.91-2.79(m, 1H), 1.94 (d, J = 9.4 Hz, 2H), 1.91-1.79(m, 2H). 13C NMR (100 MHz, DMSO) δ: 173.1, 163.9
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