Reaction Steps
N-[2-(Dimethylamino)ethyl]-N-ethyl-8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxamide was prepared by coupling 8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid and commercially available N,N-dimethyl-N'-ethylethylenediamine as described for Example 17, Step 5. The compound is purified by reverse phase HPLC on C18 silica gel (gradient elution from 0.1% trifluoroacetic acid in 5% MeCN/H2O to 100% MeCN). Neutralization of the trifluroacetate salt after concentrating the fractions from the HPLC run afforded the title compound as an amorphous solid that was triturated in ether: mp 120°-123 ° C.; 1H NMR (Me2SO-d6, 400 MHz), 1:1 mixture of amide rotamers, a: b) δ 9.00 (s, 1Ha), 8.94 (s, 1Hb), 8.54 (s, 1Ha), 8.51 (s, 1Hb), 7.99 (d, J=7.9 Hz, 1Hb), 7.96 (d, J=8.1 Hz, 1Ha), 7.73 (d, J=8.5 Hz, 2Hb), 7.69 (m, 2Ha, 1 H), 7.49 (t, J=8.1 Hz, 1 H), 7.30 (m, 5 H), 7.26 (d, J=8.3 Hz, 1 H), 6.89 (d, J=8.7 Hz, 2Hb), 6.85 (d, J=8.5 Hz, 2Ha), 3.96 (s, 3 H), 3.74(m, 1 H), 3.46(s, 2H),3.11 (m, 4H),2.80(d,J=10.4Hz, 2H),2.18(t,J=5.6 Hz, 2Hb), 2.02 (m, 2 H), 1.99 (s, 6Hb), 1.83 (s, 6Ha), 1.70 (m, 2 H, 2Ha), 1.56 (qd, J=10.8, 3.6Hz, 2 H), 0.91 (t, J=6.9 Hz, 3Hb), 0.61 (t, J=6.9 Hz, 3Ha).
