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H. I. Ali et al. / Bioorg. Med. Chem. 15 (2007) 6336–6352
4.11 (3H, s, 10-Me), 7.44 (1H, dt, J6,7 = 8.7 Hz,
J7,8 = 7.8 Hz, J7,9 = 1.5 Hz, 7-H), 7.64 (1 H, d,
J8,9 = 8.7 Hz, 9-H), 7.80 (1H, dt, J7,8 = 7.8, Hz
J8,9 = 8.7 Hz, J6,8 = 1.5 Hz, 8-H), 7.87 (1H, dd,
J6,7 = 8.7 Hz, J6,8 = 1.5 Hz, 6-H), 8.93 (1H, s, 5-H); Anal.
calcd for C17H18N4OÆ0.1H2O: C, 68.94; H, 6.19; N, 18.92.
Found: C, 68.66; H, 6.17; N, 18.89.
4.1.48. 7,10-Dimethyl-2-piperidinopyrimido[4,5-b]quino-
lin-4-(10H)-one (7j). Yield, (1.48 g, 96%); mp 292–
293 °C (from DMF); UV (EtOH): kmax/nm (log e/
dm3 molꢀ1 cmꢀ1): 222 (4.72), 275 (4.71), 283sh (4.64),
322 (4.13), 391sh (4.18), 415 (4.38), 440 (4.33); IR
(mmax/cmꢀ1): 1640 (CO); 1H NMR (CDCl3): d 1.67
(6H, br s, 30, 40 and 50-CH2), 2.49 (3H, s, 7-Me), 3.97–
4.06 (4H, m, 20 and 60-CH2), 4.09 (3H, s, 10-Me), 7.53
(1H, d, J8,9 = 9.3 Hz, 9-H), 7.58–7.65 (2H, m, 6 and 8-
H), 8.86 (1H, s, 5-H); Anal. calcd for C18H20N4OÆ1.1-
H2O: C, 65.87; H, 6.82; N, 17.07. Found: C, 66.16; H,
7.22; N, 17.16.
4.1.44.
7-Chloro-10-methyl-2-morpholinopyrimido[4,5-
b]quinolin-4(10H)-one (7f). Yield, (1.29 g, 78%), mp
>300 °C (from DMF); UV (EtOH): kmax/nm (log e/
dm3 molꢀ1 cmꢀ1): 225 (4.65), 276 (4.61), 286sh (4.53),
319 (4.02), 392sh (4.07), 416 (4.23), 441 (4.19); IR (mmax
/
cmꢀ1): 1660 (CO); H NMR (CDCl3): d 3.73–3.82 (4H,
m, 20 and 60-NCH2), 4.03-4.15 (4H, m, 30 and 50-OCH2),
4.11 (3H, s, 10-Me), 7.61 (1H, d, J8,9 = 9.0 Hz, 9-H),
7.77 (1H, dd, J8,9 = 9.0 Hz, J6,8 = 2.4 Hz, 8-H), 7.85
(1H, d, J6,8 = 2.4 Hz, 6-H), 8.87 (1H, s, 5-H); Anal. calcd
for C16H15ClN4O2Æ0.4H2O: C, 56.86; H, 4.71; N, 16.58.
Found: C, 56.86; H, 4.61; N, 16.24.
4.1.49. 10-Ethyl-7-methyl-2-morpholinopyrimido[4,5-b]-
quinolin-4-(10H)-one (7k). Yield, (1.27 g, 78%); mp
>300 °C (from DMF); UV (EtOH): kmax/nm (log e/
dm3 molꢀ1 cmꢀ1): 225 (4.63), 274 (4.62), 283sh (4.55),
326 (4.12), 387sh (4.09), 413 (4.32), 437 (4.29); IR
(mmax/cmꢀ1): 1650 (CO); 1H NMR (CDCl3): d 1.48
(3H, t, J = 7.2 Hz, 10-CH2-CH3), 2.51 (3H, s, 7-Me),
3.70–3.85 (4H, m, 20 and 60-NCH2), 3.99–4.16 (4 H,
m, 30 and 50-OCH2), 4.76 (2H, q, J = 7.2 Hz, 10-CH2-
CH3), 7.48 (1H, d, J8,9 = 9.3 Hz, 9-H), 7.64–7.68 (2H,
m, 6 and 8-H), 8.93 (1H, s, 5-H); Anal. calcd for
C18H20N4O2: C, 66.65; H, 6.21; N, 17.27. Found: C,
66.44; H, 6.37; N, 17.40.
1
4.1.45. 10-Methyl-2-morpholinopyrimido[4,5-b]quinolin-
4-(10H)-one (7g). Yield, (1.47 g, 99%); mp 296–298 °C
(decomp. from DMF); UV (EtOH): kmax/nm (log e/
dm3 molꢀ1 cmꢀ1): 220 (4.63), 272 (4.60), 279sh (4.55),
319 (4.07), 383sh (4.08), 406 (4.26), 431 (4.20); IR (mmax
/
1
cmꢀ1): 1650 (CO); H NMR (CDCl3): d 3.74–3.83 (4H,
m, 20 and 60-NCH2), 4.04–4.13 (4H, m, 30 and 50-
4.1.50.
7-Chloro-10-methyl-2-(4-methylpiperazinyl)-
OCH2), 4.14 (3H, s,10-Me), 7.48 (1H, t, J6,7
=
pyrimido[4,5-b]quinolin-4-(10H)-one (7l). Yield, (1.46 g,
85%); mp >300 °C (decomp. from DMF); UV (EtOH):
J7,8 = 7.8 Hz, 7-H), 7.68 (1H, d, J8,9 = 8.7 Hz, 9-H), 7.85
(1H, dt, J7,8 = 7.8 Hz, J8,9 = 8.7 Hz, J6,8 = 1.5 Hz, 8-H),
7.91 (1 H, d, J6,7 = 7.8 Hz, 6-H), 8.99 (1 H, s, 5-H); Anal.
calcd for C16H16N4O2Æ0.4 H2O: C, 63.31; H, 5.58; N,
18.46. Found: C, 63.61; H, 5.84; N, 18.41.
k
max/nm (log e/dm3 molꢀ1 cmꢀ1): 225 (4.65), 275 (4.65),
284sh (4.59), 319 (4.02), 390sh (4.09), 416 (4.27), 442
1
(4.21); IR (mmax/cmꢀ1): 1660 (CO); H NMR (CDCl3):
d 2.34 (3H, s, 40-Me), 2.45–2.53 (4H, m, 30 and 50-
CH2), 4.05–4.15 (4H, m, 20 and 60-CH2), 4.10 (3H, s,
10-Me), 7.60 (1H, d, J8,9 = 9.0 Hz, 9-H), 7.75 (1H, dd,
J8,9 = 9.0 Hz, J6,8 = 2.1 Hz, 8-H), 7.81 (1 H, d,
J6,8 = 2.1 Hz, 6-H), 8.82 (1H, s, 5-H); Anal. calcd for
C17H18ClN5OÆ0.1H2O: C, 59.08; H, 5.31; N, 20.26.
Found: C, 58.72; H, 5.43; N, 20.69.
4.1.46. 10-Methyl-2-(4-methylpiperazinyl)pyrimido[4,5-
b]quinolin-4-(10H)-one (7h). Yield, (1.08 g, 70%); mp
235–237 °C (decomp. from DMF); UV (EtOH): kmax
/
nm (log e/dm3 molꢀ1 cmꢀ1): 220 (4.56), 272 (4.56),
277sh (4.53), 322 (3.99), 382sh (4.06), 407 (4.24), 430
(4.17); IR (mmax/cmꢀ1): 1650 (CO); 1H NMR (CDCl3): d
2.35 (3H, br s, 40-Me), 2.42–2.58 (4H, m, 30 and 50-
CH2), 4.06–4.11 (4H, m, 20 and 60-CH2), 4.13 (3H, s,10-
Me), 7.46 (1H, t, J6,7 = J7,8 = 7.8 Hz, 7-H), 7.68 (1H, d,
J8,9 = 9.0 Hz, 9-H), 7.83 (1H, dt, J7,8 = 7.8 Hz,
J8,9 = 9.0 Hz, J6,8 = 1.5 Hz, 8-H), 7.91 (1H, d,
J6,7 = 7.8 Hz, 6-H), 8.96 (1H, s, 5-H); Anal. calcd for
C17H19N5OÆ0.4H2O: C, 64.50; H, 6.30; N, 22.12. Found:
C, 64.28; H, 6.22; N, 21.92.
4.1.51. 7-Chloro-10-methyl-2-piperidinopyrimido[4,5-b]-
quinolin-4-(10H)-one (7m). Yield, (1.46 g, 89%); mp
>300 °C (from DMF); UV (EtOH): kmax/nm (log e/
dm3 molꢀ1 cmꢀ1): 226 (4.77), 276 (4.78), 286sh (4.71),
317 (4.11), 393sh (4.24), 420 (4.41), 445 (4.35); IR
(mmax/cmꢀ1): 1645 (CO); 1H NMR (CDCl3): d 1.70
(6H, br s, 30, 40 and 50-CH2), 3.96–4.06 (4H, m, 20 and
60-NCH2), 4.08 (3H, s, 10-Me), 7.57 (1H, d,
J8,9 = 9.0 Hz, 9-H), 7.72 (1H, d, J8,9 = 9.0 Hz, 8-H),
7.79 (1H, s, 6-H), 8.79 (1H, s, 5-H); Anal. calcd for
C17H17ClN4OÆ1.1H2O: C, 58.57; H, 5.55; N, 16.07.
Found: C, 58.23; H, 5.46; N, 15.82.
4.1.47. 7-Methoxy-10-methyl-2-morpholinopyrimido[4,5-
b]quinolin-4-(10H)-one (7i). Yield, (1.57 g, 96%); mp
296–299 °C (decomp. from DMF); UV (EtOH): kmax
nm (log e/dm3 molꢀ1 cmꢀ1): 226 (4.47), 276 (4.49), 328
(4.03), 400sh (3.92), 427 (4.16), 453 (4.18); IR (mmax
/
/
4.1.52.
quinolin-4-(10H)-one (7n). Yield, (1.28 g, 79%); mp
287–289 °C (decomp. from DMF); UV (EtOH): kmax
nm (log e/dm3 molꢀ1 cmꢀ1): 225 (4.75), 276 (4.70), 336
7,8,10-Trimethyl-2-morpholinopyrimido[4,5-b]-
cmꢀ1): 1655 (CO); 1H NMR (CDCl3): d 3.72–3.82
(4H, m, 20 and 60-NCH2), 3.93 (3H, s, 7-OMe), 4.00–
4.12 (4H, m, 30 and 50-OCH2), 4.13 (3H, s, 10-Me),
7.22 (1H, d, J6,8 = 2.7 Hz, 6-H), 7.47 (1H, dd,
J8,9 = 9.3 Hz, J6,8 = 2.7 Hz, 8-H), 7.68 (1H, d,
J8,9 = 9.3 Hz, 9-H), 8.91 (1H, s, 5-H); Anal. calcd for
C17H18N4O3ÆH2O: C, 59.29; H, 5.85; N, 16.27. Found:
C, 59.30; H, 5.76; N, 15.89.
/
(4.18), 387sh (4.15), 410 (4.38), 434 (4.67); IR (mmax
/
1
cmꢀ1): 1650 (CO); H NMR (CDCl3): d 2.41 (3H, s, 7-
Me), 2.52 (3H, s, 8-Me), 3.73–3.81 (4H, m, 20 and 60-
NCH2), 4.02–4.09 (4H, m, 30 and 50-OCH2), 4.11 (3H,
s, 10-Me), 7.44 (1H, s, 9-H), 7.60 (1H, s, 6 H), 8.91