Biphenyl-4-sulfonic acid [3-(7-chloro-quinolin-4-ylamino)-propyl]-amide (27)

Pale yellowish white solid; 70% yield; mp 116–118 °C; IR (KBr, cm⁻¹): 3260.9 (NH); 1180.5 (SO₂); ¹H NMR (500 MHz, CDCl₃): δ 1.82–1.85 (m, 2 H, CH₂), 2.89–2.94 (m, 2 H, CH₂), 3.48–3.52 (m, 2 H, CH₂), 6.30–6.31 (d, J = 5.0 Hz, 1 H, Ar-H), 6.92 (br s, 1 H, NH D₂O exchangeable), 7.28–7.29 (d, J = 5.0 Hz, 1 H, Ar-H), 7.32–7.35 (d, J = 10.0 Hz, 1 H, Ar-H), 7.38–7.40 (d, J = 10.0 Hz, 1 H, Ar-H), 7.49–7.51 (d, J = 10.0 Hz, 1 H, Ar-H), 7.54 (s, 1 H, Ar-H), 7.59–7.61 (d, J = 10.0 Hz, 2 H, Ar-H), 7.63–7.65 (d, J = 10.0 Hz, 2 H, Ar-H), 7.70 (s, 1 H, Ar-H), 7.77 (br s, 1 H, NH D₂O exchangeable), 7.82–7.84 (d, J = 10.0 Hz, 1 H, Ar-H), 8.02–8.04 (d, J = 10.0 Hz, 1 H, Ar-H), 8.30–8.31 (d, J = 5.0 Hz, 1 H, Ar-H); ¹³C NMR (125 MHz, CDCl₃): δ 22.55, 27.69, 40.62, 98.57, 117.42, 123.29, 124.93 (2 C), 127.04 (2 C), 127.17 (2 C), 127.37 (2 C), 127.51 (2 C), 128.41, 129.05, 134.99, 139.14, 144.91, 147.91, 150.67, 150.87; ES-MS m/z 453 [M + H]⁺; Anal.Calcd for C₂₄H₂₂ClN₃O₂S: C, 63.78; H, 4.91; N, 9.30; found: C, 63.74; H, 4.89; N, 9.28.