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M. Farooqui et al. / European Journal of Medicinal Chemistry 44 (2009) 794e799
5.9. 3-[3-(4-Acetylamino-benzyl)-[1,2,4]oxadiazol-5-yl]-
N-(2-fluoro-phenyl)-propionamide (7e)
2H, each eCH2e), 3.95 (s, 2H, eCH2ePh), 6.8 (d, 1H, Ar-
H), 7.3e7.17 (m, 3H, Ar-H), 7.29 (d, 1H, Ar-H), 7.35 (s,
1H, Ar-H), 7.46 (d, 2H, Ar-H), 9.8 (s, 1H, eNH), 9.93 (s,
1H, eNH). Mass (m/z): 379 (Mþ1). Anal. Found: C, 67.05;
H, 6.26; N, 15.20. Calcd for C22H22N4O3: C, 66.65; H, 5.86;
N, 14.80%.
Prepared from 2-fluoroaniline (0.10 g, 0.35 mmol) and
compound 6 (0.10 g, 0.35 mmol) by using the same procedure
mentioned in 7a to afford 7e as cream-colored solid (95 mg,
72%).
M.p. 147e148 ꢁC. IR (cmꢂ1, KBr): 3265, 3095, 1662,
1
1605, 1599 and 1575. H NMR (DMSO-d6): d 2.0 (s, 3H,
5.13. 3-[3-(4-Acetylamino-benzyl)-[1,2,4]oxadiazol-5-
CH3), 2.95 and 3.13 (each t, each 2H, each eCH2e), 3.95
(s, 2H, eCH2ePh), 7.10 (m, 2H, Ar-H), 7.16 (d, 2H, Ar-H
d), 7.21 (m, 1H, Ar-H), 7.46 (d, 2H, Ar-H), 7.78 (1H, broad
s, Ar-H), 9.82 (s, 1H, eNH) and 9.86 (s, 1H, eNH). Mass
(m/z): 383 (Mþ1). Anal. Found: 63.20; H, 5.39; N, 15.03.
Calcd for C21H19FN4O4: C, 62.82; H, 5.01; N, 14.65%.
yl]-N-(3-ethynyl-phenyl)-propionamide (7l)
Prepared from 3-ethynylaniline (0.10 g, 0.35 mmol) and
compound 6 (0.10 g, 0.35 mmol) by using the same procedure
mentioned in 7a to obtain 7l as pale yellow solid (105 mg,
78.4%).
M.p. 194e195 ꢁC. IR (cmꢂ1, KBr): 3257, 3111, 1666,
1
1607, 1586 and 1544. H NMR (DMSO-d6): d 2.0 (s, 3H,
5.10. 3-[3-(4-Acetylamino-benzyl)-[1,2,4]oxadiazol-5-
yl]-N-(2,4-difluoro-phenyl)-propionamide (7g)
CH3), 2.85 (t, 2H, CH2e), 4.15 (s, 1H, acetylene), 3.25 (t,
2H, CH2e), 4.0 (s, 2H, eCH2eAr), 7.15 (m, 3H, Ar-H),
7.2e7.25 (m, 1H, Ar-H), 7.4e7.50 (m, 3H, Ar-H), 7.7 (s,
1H, Ar-H) 9.86, 10.13 (each s, each 1H, each eNH protons).
Mass (m/z): 389 (Mþ1). Anal. Found: C, 68.33; H, 5.49; N,
14.72. Calcd for C22H20N4O3: C, 68.03; H, 5.19; N, 14.42%
Prepared from 2,4-difluoroaniline (0.10 g, 0.35 mmol) and
compound 6 (0.10 g, 0.35 mmol) by using the same procedure
mentioned in 7a to obtain 7g as pale yellow solid (110 mg,
80.3%).
M.p. 147e148 ꢁC. IR (cmꢂ1, KBr): 3260, 3100, 1672, 1600,
1589 and 1555. 1H NMR (DMSO-d6): d 2.0 (s, 3H, CH3), 2.85
and 3.15 (each t, each 2H, each eCH2e), 4.0 (s, 2H, eCH2ePh),
7 (t, 1H, Ar-H), 7.16 (d, 2H, Ar-H), 7.23e7.29 (m, 1H, Ar-H),
7.4 (d, 2H, Ar-H), 7.7 (m, 1H, Ar-H), 9.82 (m, 1H, N-H), 9.87 (s,
1H, eNH) Mass (m/z): 400 (Mþ1). Anal. Found: C, 63.22; H,
5.41; N, 15.05. Calcd for C21H18 F2N4O3: C, 62.82; H, 5.01;
N, 14.65%.
5.14. 3-[3-(4-Acetylamino-benzyl)-[1,2,4]oxadiazol-5-
yl]-N-pyridin-3-yl-propionamide (7m)
Procedure. Prepared from 3-aminopyridine (0.10 g,
0.35 mmol) and compound 6 (0.10 g, 0.35 mmol) by using
the same procedure mentioned in 7a to obtain 7m as cream-
colored solid (100 mg, 79.4%).
5.11. 3-[3-(4-Acetylamino-benzyl)-[1,2,4]oxadiazol-5-
yl]-N-(4-trifluoromethyl-phenyl)-propionamide (7k)
M.p. 189e190 ꢁC. IR (cmꢂ1, KBr): 3288, 3070, 1666,
1
1607, 1586 and 1544. H NMR (DMSO-d6) d 2.0 (s, 3H,
CH3), 2.85 and 3.15 (each t, each 2H, each eCH2e), 4.0 (s,
2H, eCH2eAr), 7.2e7.25 (d, 2H, Ar-H), 7.4 (d, 2H, Ar-H),
7.45 (m, 1H, Py-H), 8.4 (m, 1H, Py-H), 8.75 (dd, 1H, Py-H),
8.95 (d, 1H, Py-H), 9.8 (s, 1H, eNH) and 9.98 (s, 1H,
eNH). Mass (m/z): 366 (Mþ1). Anal. Found: C, 62.80; H,
5.60; N, 19.52. Calcd for C19H19N5O3: C, 62.46; H, 5.24; N,
19.17%.
Prepared from 4-trifluoromethylaniline (0.10 g, 0.35 mmol)
and compound 6 (0.10 g, 0.35 mmol) by using the same pro-
cedure mentioned in 7a to obtain 7k as pale yellow solid
(110 mg, 73.3%).
M.p. 201e202 ꢁC. IR (cmꢂ1, KBr): 3267, 3090, 1677,
1
1625, 1589 and 1567. H NMR (DMSO-d6): d 2.2 (s, 3H,
CH3), 2.95 and 3.2 (each t, each 2H, each eCH2e), 4.0 (s,
2H, eCH2ePh), 7.15 (d, 2H, eNH), 7.45 (d, 2H, Ar-H),
7.63 and 7.72 (each d, each 2H, Ar-H), 9.86 and 10.39 (each
s, each 1H, each eNH). Mass (m/z): 433 (Mþ1). Anal. Found:
C, 58.75; H, 4.80; N, 13.33. Calcd for C21H19F3N4O3: C,
58.33; H, 4.43; N, 12.96%.
5.15. 3-[3-(4-Acetylamino-benzyl)-[1,2,4]oxadiazol-5-
yl]-N-benzyl-propionamide (7n)
Prepared from benzyl amine (0.10 g, 0.35 mmol) and 6
(0.10 g, 0.35 mmol) by using the same procedure mentioned
in 7a to obtain 7n as white solid (120 mg, 92.3%).
5.12. 3-[3-(4-Acetylamino-benzyl)-[1,2,4]oxadiazol-5-
yl]-N-m-tolyl-propionamide (7j)
M.p. 163e164 ꢁC. IR (cmꢂ1, KBr): 3257, 3111, 1666,
1
1607, 1586 and 1544. H NMR (DMSO-d6): d 2.0 (s, 3H,
Prepared from m-toludine (0.10 g, 0.35 mmol) and com-
pound 6 (0.10 g, 0.35 mmol) by using the same procedure
mentioned in 7a to obtain 7j as white solid (115 mg, 88.5%).
M.p. 152e153 ꢁC. IR (cmꢂ1, KBr): 3240, 3120, 1680,
1615, 1599 and 1570. H NMR (DMSO-d6): d 2.0 (s, 3H,
CH3), 2.23 (s, 3H, AreCH3), 2.81 and 3.12 (each t, each
CH3), 2.65 (t, 2H, CH2e), 3.15 (t, 2H, CH2e), 3.95 (s, 2H,
eCH2eAr), 4.23 (s, 2H, Ar-CH2) 7.15e7.22 (m, 5H, Ar-H),
7.25 (m, 2H, Ar-H), 7.47e7.49 (d, 2H, Ar-H), 8.4 (s, 1H,
eNH) 9.88(s, 1H, -NH). Mass (m/z): 379 (Mþ1). Anal. Found:
C, 66.96; H, 6.24; N, 15.17. Calcd for C21H22N4O3: C, 66.65;
H, 5.86; N, 14.80%.
1