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. 2017 Feb 21;8(15):24635–24643. doi: 10.18632/oncotarget.15601

Scheme 1. Synthesis of target compound IMB-1406.

Scheme 1

(2R)-2-(2-(((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)((R)-1-hydroxybutan-2-yl)amino)ethylamino)butan-1-ol (IMB-1406); 1H NMR (400 MHz, DMSO-d6) δ 8.70 (s, 1H), 8.12 (d, J = 2.0 Hz, 1H), 7.73–7.66 (m, 2H), 7.34 (d, J = 7.2 Hz, 2H), 5.49 (s, 1H), 4.37 (brs, 1H), 3.89 (s, 3H), 3.50–3.09 (m, 5H), 2.75-2.60 (m, 3H), 2.33-2.22 (m, 2H), 2.09–2.06 (m, 1H), 1.33–1.09 (m, 4H), 0.74 (t, J = 7.2 Hz, 3H), 0.65 (t, J = 7.2 Hz, 3H); 13C NMR (101 MHz, DMSO-d6) δ 160.13, 143.42, 141.47, 136.28, 131.91, 129.69, 129.56, 129.05, 128.44, 128.03, 126.95, 126.49, 116.37, 62.41, 62.34, 60.24, 53.59, 47.08, 23.47, 21.29, 11.93, 9.82. HRMS (m/z) (ESI): calcd for C27H37BrN3O3 [M+H] +: 530.20183; found: 530.20307.