Molecules 2014, 19
8926
1H), 7.13 (dd, J = 8.6, 2.1 Hz, 1H), 3.87 (dd, J = 10.4, 5.5 Hz, 2H), 3.31 (s, 2H), 2.72–2.67 (m, 2H),
2.67–2.51 (m, 4H), 2.46 (s, 6H), 2.40–2.24 (m, 4H), 2.12 (s, 3H), 2.01–1.91 (m, 2H). 13C-NMR (CDCl3)
δ = 169.36, 160.52, 159.45, 148.55, 139.93, 136.37, 132.42, 131.75, 128.46, 126.01, 123.79, 122.85,
121.29, 120.67, 113.86, 64.20, 59.29, 54.15, 53.35, 45.80, 45.20, 42.04, 24.31. HRMS (ESI): Calcd for
(M−H)− (C26H34ClN7O) requires m/z 494.2435, found 494.2421. Anal. Calcd for C26H34ClN7O.H2O: C,
60.75; H, 7.06; N, 19.07. Found: C, 60.66; H, 6.97; N, 18.89.
N-(2-(4-(3-(Dimethylamino)propylamino)quinazolin-2-yl)phenyl)-2-morpholinoacetamide
(10e).
Compound 7 was treated with excess morpholine according to the general aminolysis procedure to
afford 10e as a white solid in 78% yield after column chromatography with petroleum ether/EtOAc
(20:1) elution; mp 179–181 °C. 1H-NMR (CDCl3) δ = 13.67 (s, 1H), 9.09 (s, 1H), 8.88 (d, J = 2.1 Hz,
1H), 8.53 (d, J = 8.6 Hz, 1H), 7.92 (d, J = 8.2 Hz, 1H), 7.77–7.69 (m, 1H), 7.62 (d, J = 8.1 Hz, 1H),
7.46 (t, J = 7.6 Hz, 1H), 7.13 (dd, J = 8.6, 2.2 Hz, 1H), 3.86 (dd, J = 10.2, 5.6 Hz, 2H), 3.64–3.53 (m,
13
4H), 3.32 (s, 2H), 2.68–2.62 (m, 2H), 2.63–2.53 (m, 4H), 2.42 (s, 6H), 1.94–1.85 (m, 2H). C-NMR
(CDCl3) δ = 168.97, 160.56, 159.40, 148.43, 140.04, 136.45, 132.35, 131.83, 128.02, 126.02, 123.51,
122.86, 121.22, 120.55, 113.89, 66.34, 64.81, 59.95, 53.78, 45.51, 42.80, 24.41. HRMS (ESI): Calcd
for (M−H)− (C25H31ClN6O2) requires m/z 481.2119, found 481.2107. Anal. Calcd for C25H31ClN6O2: C,
62.17; H, 6.47; N, 17.40. Found: C, 62.24; H, 6.36; N, 17.55.
N-(2-(4-(3-(Dimethylamino)propylamino)quinazolin-2-yl)phenyl)-3-(piperidin-1-yl)propanamide (11a).
Compound 8 was treated with excess piperidine according to the general aminolysis procedure to
afford 11a as a white solid in 69% yield after column chromatography with petroleum ether/EtOAc
(15:1) elution; mp 178–179 °C. 1H-NMR (CDCl3) δ = 14.06 (s, 1H), 9.06 (s, 1H), 8.85 (d, J = 2.0 Hz,
1H), 8.66 (d, J = 8.6 Hz, 1H), 7.79–7.68 (m, 2H), 7.59 (d, J = 8.1 Hz, 1H), 7.48–7.40 (m, 1H), 7.08 (dd,
J = 8.6, 2.1 Hz, 1H), 3.84 (dd, J = 10.2, 5.5 Hz, 2H), 2.92–2.82 (m, 2H), 2.80–2.71 (m, 2H), 2.67–2.58
(m, 2H), 2.54–2.42 (m, 4H), 2.40 (s, 6H), 1.96–1.85 (m, 2H), 1.61–1.53 (m, 4H), 1.46–1.37 (m, 2H).
13C-NMR (CDCl3) δ = 170.93, 160.60, 159.11, 148.02, 141.16, 136.75, 132.58, 131.74, 127.45,
125.93, 122.33, 121.79, 121.21, 120.01, 113.86, 59.94, 54.99, 54.42, 45.51, 42.83, 36.52, 25.97, 24.39,
24.30. HRMS (ESI): Calcd for (M−H)− (C27H35ClN6O) requires m/z 493.2483, found 493.2472. Anal.
Calcd for C27H35ClN6O: C, 65.51; H, 7.13; N, 16.98. Found: C, 65.70; H, 7.24; N, 16.86.
N-(2-(4-(3-(Dimethylamino)propylamino)quinazolin-2-yl)phenyl)-3-(pyrrolidin-1-yl)propanamide (11b).
Compound 8 was treated with excess pyrrolidine according to the general aminolysis procedure to
afford 11b as a white solid in 71% yield after column chromatography with petroleum ether/EtOAc (15:1)
elution; mp 163–165 °C 1H-NMR (CDCl3) δ = 14.12 (s, 1H), 9.07 (s, 1H), 8.86 (d, J = 2.0 Hz, 1H), 8.67 (d,
J = 8.6 Hz, 1H), 7.74 (dt, J = 14.9, 7.6 Hz, 2H), 7.60 (d, J = 8.1 Hz, 1H), 7.45 (dd, J = 11.0, 3.9 Hz, 1H),
7.10 (dd, J = 8.6, 2.1 Hz, 1H), 3.87 (dd, J = 10.2, 5.5 Hz, 2H), 3.01 (t, J = 7.5 Hz, 2H), 2.82 (t, J = 7.5 Hz,
13
2H), 2.74–2.55 (m, 6H), 2.41 (s, 6H), 1.97–1.88 (m, 2H), 1.86–1.74 (m, 4H). C-NMR (CDCl3)
δ = 170.62, 160.68, 159.16, 148.07, 141.15, 136.84, 132.64, 131.73, 127.50, 125.94, 122.39, 121.81,
121.19, 120.09, 113.88, 59.96, 54.18, 52.08, 45.51, 42.84, 38.41, 24.40, 23.52. HRMS (ESI): Calcd for
(M−H)− (C26H33ClN6O) requires m/z 479.2326, found 479.2318. Anal. Calcd for C26H33ClN6O: C,
64.92; H, 6.91; N, 17.47. Found: C, 65.02; H, 6.68; N, 17.55.