Arch. Pharm. Chem. Life Sci. 2011, 11, 158–164
Bromo-hydroxyimidazo[1,2-a]pyridine-3-carboxylates
163
1094.9, 1076.4; 1H-NMR (CDCl3, ppm) d: 1.40 (t, 3H, J ¼ 7.1 Hz,
–CH2CH3), 2.33 (s, 3H, –NCH3), 2.65 (m, 8H, –piperazinyl), 3.99 (s,
2H, –CH2N–), 4.38 (q, 2H, J ¼ 7.1 Hz, –CH2CH3), 4.53 (s, 2H,
–CH2S–), 7.22 (d, 2H, J ¼ 7.9 Hz, –PhH), 7.40 (d, J ¼ 8.1 Hz, 2H,
–PhH), 9.04 (s, 1H, C5-H); MS (ESI) m/z: 553.7, 555.6 [M þ H]þ. Anal.
calcd. for C23H26BrClN4O3S (%): C, 49.87; H, 4.73; N, 10.11. Found
(%): C, 50.13; H, 4.81; N, 9.98.
1079.5 (nC–Br); 1H-NMR (CDCl3, ppm) d: 1.36 (t, 3H, J ¼ 6.9 Hz,
–CH2CH3), 1.92 (s, 4H, –pyrrolidinyl), 2.29 (s, 3H, p-CH3-
phenyl), 2.80 (s, 4H, –pyrrolidinyl), 4.12 (s, 2H, –CH2N–), 4.31
(q, 2H, J ¼ 7.0 Hz, –CH2CH3), 4.52 (s, 2H, –CH2S–), 7.06 (d, 2H,
J ¼ 7.2 Hz, –PhH), 7.35 (d, 2H, J ¼ 6.7 Hz, –PhH), 9.01 (s, 1H, C5-H);
MS (ESI) m/z: 504.0, 505.9 [M þ H]þ. Anal. calcd.
for C23H26BrN3O3S (%): C, 54.76; H, 5.20; N, 8.33. Found (%): C,
54.83; H, 5.29; N, 8.21.
Ethyl 6-bromo-2-((4-bromophenylthio)methyl)-7-
((dimethylamino)methyl)-8-hydroxyimidazo[1,2-a]pyridine-
Ethyl 6-bromo-8-hydroxy-7-(morpholinomethyl)-2-(p-
tolylthiomethyl)imidazo[1,2-a]pyridine-3-carboxylate 10o
3-carboxylate 10j
Light yellow solid, yield: 57.6%; m.p.: 133–1358C; IR (KBr, cmꢁ1):
3424.3 (nOH), 1695.6 (nC O), 2978.5, 1473.7, 1401.0, 1332.7, 1067.5;
Light pink solid, yield: 78.2%; m.p.: 202–2048C; IR (KBr, cmꢁ1):
3430.1 (nOH), 1699.0 (nC O), 2923.3, 1491.4, 1399.9, 1332.8,
–
–
–
–
1077.3; 1H-NMR (CDCl3, ppm) d: 1.39 (t, 3H, J ¼ 7.1 Hz,
–CH2CH3), 2.30 (s, 3H, p-CH3-phenyl), 2.81 (s, 4H, –morpholino),
3.84 (s, 4H, –morpholino), 4.04 (s, 2H, –CH2N–), 4.34 (q, 2H, J ¼ 7.1
Hz, –CH2CH3), 4.49 (s, 2H, –CH2S–), 7.09 (d, 2H, J ¼ 7.1 Hz, –PhH),
7.34 (d, 2H, J ¼ 6.8 Hz, –PhH), 9.08 (s, 1H, C5-H); MS (ESI) m/z:
520.1, 522.0 [M þ H]þ. Anal. calcd. for C23H26BrN3O4S (%): C,
53.08; H, 5.04; N, 8.07. Found (%): C, 52.89; H, 5.07; N, 8.11.
1H-NMR (CDCl3, ppm) d: 1.39 (t, 3H, J ¼ 7.1 Hz, –CH2CH3), 2.55 (s, 6H,
–N(CH3)2), 4.05 (s, 2H, –CH2N–), 4.39 (q, 2H, J ¼ 7.0 Hz, –CH2CH3),
4.53 (s, 2H, –CH2S–), 7.29–7.36 (m, 4H, –PhH), 8.98 (s, 1H, C5-H); MS
(ESI) m/z: 542.3, 544.1 [M þ H]þ. Anal. calcd. for C20H21Br2N3O3S (%):
C, 44.22; H, 3.90; N, 7.73. Found (%): C, 44.53; H, 4.01; N, 7.66.
Ethyl 6-bromo-2-((4-bromophenylthio)methyl)-8-hydroxy-
7-(morpholinomethyl)imidazo[1,2-a]pyridine-3-carboxylate
10k
Ethyl 6-bromo-8-hydroxy-2-((3-
methoxyphenylthio)methyl)-7-(pyrrolidin-1-
Light pink solid, yield: 72.0%; m.p.: 158–1608C; IR (KBr, cmꢁ1):
3421.3 (nOH), 1699.8 (nC O), 2924.0, 1473.9, 1400.9, 1332.9,
ylmethyl)imidazo[1,2-a]pyridine-3-carboxylate 10p
Light yellow solid, yield: 76.5%; m.p.: 122–1248C; IR (KBr, cmꢁ1):
–
–
1077.3; 1H-NMR (CDCl3, ppm) d: 1.40 (t, 3H, J ¼ 7.1 Hz,
–CH2CH3), 2.81 (s, 4H, –morpholino), 3.85 (s, 4H, –morpholino),
4.01 (s, 2H, –CH2N–), 4.38 (q, 2H, J ¼ 7.2 Hz, –CH2CH3), 4.50 (s, 2H,
–CH2S–), 7.34 (m, 4H, –PhH), 9.02 (s, 1H, C5-H); MS (ESI) m/z: 584.1,
586.1 [M þ H]þ. Anal. calcd. for C22H23Br2N3O4S (%): C, 45.14; H,
3.96; N, 7.18. Found (%): C, 45.42; H, 4.06; N, 7.11.
3425.8 (nOH), 1692.1 (nC O), 2959.2, 1589.7, 1477.4, 1401.1,
–
–
1329.8, 1078.4; 1H-NMR (CDCl3, ppm) d: 1.38 (t, 3H, J ¼ 7.1 Hz,
–CH2CH3), 1.91 (s, 4H, –pyrrolidinyl), 2.81 (s, 4H, –pyrrolidinyl),
3.79 (s, 3H, –OCH3), 4.12 (s, 2H, –CH2N–), 4.36 (q, 2H, J ¼ 6.8 Hz,
–CH2CH3), 4.56 (s, 2H, –CH2S–), 6.68 (d, 1H, J ¼ 7.8 Hz, –PhH), 7.10
(m, 3H, –PhH), 8.89 (s, 1H, C5-H); MS (ESI) m/z: 520.0, 522.1
[M þ H]þ. Anal. calcd. for C23H26BrN3O4S (%): C, 53.08; H, 5.04;
N, 8.07. Found (%): C, 53.14; H, 5.13; N, 7.96.
Ethyl 6-bromo-2-((4-bromophenylthio)methyl)-8-hydroxy-
7-((4-methylpiperazin-1-yl)methyl)imidazo[1,2-a]pyridine-
3-carboxylate 10l
Ethyl 6-bromo-8-hydroxy-2-((3-
methoxyphenylthio)methyl)-7-(piperidin-1-
Light yellow solid, yield: 65.9%; m.p.: 146–1478C; IR (KBr, cmꢁ1):
3422.5 (nOH), 1683.2 (nC O), 2924.2, 1471.6, 1396.7, 1330.3,
–
–
ylmethyl)imidazo[1,2-a]pyridine-3-carboxylate 10q
White solid, yield: 80.6%; m.p.: 150–1528C; IR (KBr, cmꢁ1): 3422.0
(nOH), 1690.9 (nC O), 2934.7, 1589.7, 1476.2, 1399.6, 1336.3,
1071.3; 1H-NMR (CDCl3, ppm) d: 1.40 (t, 3H, J ¼ 7.1 Hz,
–CH2CH3), 2.35 (s, 3H, –NCH3), 2.76 (m, 8H, –piperazinyl), 4.00
(s, 2H, –CH2N–), 4.38 (q, 2H, J ¼ 7.1 Hz, –CH2CH3), 4.53 (s, 2H,
–CH2S–), 7.31–7.40 (m, 4H, –PhH), 9.05 (s, 1H, C5-H); MS (ESI) m/z:
597.0, 599.0 [M þ H]þ. Anal. calcd. for C23H26Br2N4O3S (%): C,
46.17; H, 4.38; N, 9.36. Found (%): C, 46.37; H, 4.48; N, 9.24.
–
–
1078.0; 1H-NMR (CDCl3, ppm) d: 1.39 (t, 3H, J ¼ 7.0 Hz,
–CH2CH3), 1.55 (s, 2H, –piperidinyl), 1,70 (s, 4H, –piperidinyl),
2.67 (s, 4H, –piperidinyl), 3.80 (s, 3H, –OCH3), 3.95 (s, 2H, –CH2N–),
4.36 (q, 2H, J ¼ 7.0 Hz, –CH2CH3), 4.57 (s, 2H, –CH2S–), 6.70 (d, 1H,
J ¼ 7.8 Hz, –PhH), 7.11 (m, 3H, –PhH), 9.02 (s, 1H, C5-H); MS (ESI)
m/z: 534.0, 536.0 [M þ H]þ. Anal. calcd. for C24H28BrN3O4S (%): C,
53.93; H, 5.28; N, 7.86. Found (%): C, 54.02; H, 5.38; N, 7.78.
Ethyl 6-bromo-7-((dimethylamino)methyl)-8-hydroxy-2-(p-
tolylthiomethyl)imidazo[1,2-a]pyridine-3-carboxylate 10m
White solid, yield: 69.6%; m.p.: 191–1938C; IR (KBr, cmꢁ1): 3408.4
(nOH), 1694.4 (nC O), 2976.9, 1597.6, 1494.0, 1402.6, 1326.5, 1080.4;
–
–
Ethyl 6-bromo-8-hydroxy-2-((3-methoxyphenylthio)- methyl)-
7-(morpholinomethyl)imidazo[1,2-a]pyridine-3-carboxylate
10r
1H-NMR (CDCl3, ppm) d: 1.36 (t, 3H, J ¼ 6.9 Hz, –CH2CH3), 2.29 (s, 3H,
p-CH3-phenyl), 2.46 (s, 6H, –N(CH3)2), 3.96 (s, 2H, –CH2N–), 4.32 (q, 2H,
J ¼ 6.8 Hz, –CH2CH3), 4.53 (s, 2H, –CH2S–), 7.06 (d, 2H, J ¼ 7.1 Hz,
–PhH), 7.34 (d, 2H, J ¼ 6.7 Hz, –PhH), 9.04 (s, 1H, C5-H); MS (ESI) m/z:
478.1, 480.0 [M þ H]þ. Anal. calcd. for C21H24BrN3O3S (%): C, 52.72;
H, 5.06; N, 8.78. Found (%): C, 52.80; H, 5.15; N, 8.65.
Light yellow solid, yield: 76.0%; m.p.: 167–1698C; IR (KBr, cmꢁ1):
3424.1 (nOH), 1692.6 (nC O), 2933.1, 1589.5, 1476.2, 1400.1,
–
–
1332.0, 1076.2; 1H-NMR (CDCl3, ppm) d: 1.39 (t, 3H, J ¼ 7.0 Hz,
–CH2CH3), 2.70 (s, 4H, –morpholino), 3.77–3.81 (m, 7H, –morpho-
lino, –OCH3), 4.00 (s, 2H, –CH2N–), 4.37 (q, 2H, J ¼ 7.0 Hz,
–CH2CH3), 4.57 (s, 2H, –CH2S–), 6.70 (d, 1H, J ¼ 8.1 Hz, –PhH),
7.11 (m, 3H, –PhH), 9.08 (s, 1H, C5-H); MS (ESI) m/z: 536.0, 538.1
[M þ H]þ. Anal. calcd. for C23H26BrN3O5S (%): C, 51.50; H, 4.89; N,
7.83. Found (%): C, 51.67; H, 5.02; N, 7.71.
Ethyl 6-bromo-8-hydroxy-7-(pyrrolidin-1-ylmethyl)-2-(p-
tolylthiomethyl)imidazo[1,2-a]pyridine-3-carboxylate 10n
White solid, yield: 71.5%; m.p.: 190–1928C; IR (KBr, cmꢁ1):
3423.5 (nOH), 1693.0 (nC O), 2962.9, 1494.0, 1401.1, 1330.2,
–
–
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