A. B. Scheiff et al. / Bioorg. Med. Chem. 18 (2010) 2195–2203
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4.3.6. Ethyl 5-(4-chlorobenzoyl)-4-phenylthiazol-2-
ylcarbamate (16f)
2944, 1668, 1596, 1473, 1338, 1249, 1177, 1093, 1027, 904, 872,
839, 788, 757, 714, 672, 608. Elemental Anal. Calcd for
1H NMR (500 MHz, DMSO-d6) d 1.27 (t, J = 7.1 Hz, 3H), 4.26 (q,
J = 7.1 Hz, 2H), 7.16 (m, 2H), 7.22–7.27 (m, 3H), 7.31 (m, 2H),
7.51 (m, 2H), 12.35 (s, 1H). 13C NMR (125 MHz, DMSO-d6) d 14.4,
62.4, 124.8, 128.0, 128.2, 128.9, 129.8, 131.0, 134.2, 136.6, 137.1,
154.1, 155.8, 162.6, 188.0. IR (KBr cmꢀ1); 3265, 3071, 2978,
2934, 1701, 1620-, 1547, 1475, 1400, 1310, 1238, 1175, 1118,
1064, 1015, 910, 866, 830, 773, 739, 706, 669. LC/ESI-MS negative
mode 385 ([MꢀH]ꢀ), positive mode 387 ([M+H]+). Mp 180 °C. Yield
54%.
C24H18N2O3S (414.48): C, 69.55; H, 4.38; N, 6.76. Found: C, 69.39;
H, 4.59; N, 6.93. LC/ESI-MS negative mode 413 ([MꢀH]ꢀ), positive
mode 415 ([M+H]+). Mp 180–182 °C. Yield 59%.
4.3.13. N-(5-(4-Methylbenzoyl)-4-phenylthiazol-2-
yl)benzamide (16m)
1H NMR (500 MHz, CDCl3) d 2.29 (s, 3H), 7.01 (m, 2H), 7.14 (m,
3H), 7.38 (m, 2H), 7.47 (t, J = 7.72 Hz, 2H), 7.57 (m, 3H), 7.88 (d,
J = 7.88 Hz, 2H). 13C NMR (125 MHz, CDCl3) d 21.6, 126.2, 127.6,
128.1, 128.8, 128.9, 129.1, 129.4, 129.8, 131.1, 133.4, 133.6,
134.9, 143.6, 153.3, 160.0, 164.7, 189.0. IR (KBr cmꢀ1); 3280,
2934, 1675, 1630, 1528, 1475, 1401, 1339, 1287, 1238, 1150,
1120, 1087, 1029, 952, 900, 838, 782, 698, 669. Elemental Anal.
Calcd for C24H18N2O2S (398.48): C, 72.34; H, 4.55; N, 7.03. Found:
C, 72.08; H, 4.76; N, 6.98. LC/ESI-MS negative mode 397 ([MꢀH]ꢀ),
positive mode 399 ([M+H]+). Mp 180 °C. Yield 34%.
4.3.7. Phenyl(4-phenyl-2-(phenylamino)thiazol-5-yl)metha-
none (16g)
1H NMR (500 MHz, DMSO-d6) d 7.14–7.07 (m, 1H), 7.11–7.19
(m, 5H), 7.32–7.42 (m, 5H), 7.44–7.46 (m, 2H), 7.65–7.67 (m,
2H), 10.88 (s, 1H). Elemental Anal. Calcd for C22H16N2OS
(356.44): C, 74.13; H, 4.52; N, 7.86. Found: C, 74.06; H, 4.98; N,
7.86. LC/ESI-MS negative mode 355 ([MꢀH]ꢀ), positive mode 357
([M+H]+). Mp 193 °C. Yield 61%.
4.3.14. N-(5-(4-(Methylsulfonyl)benzoyl)-4-phenylthiazol-2-
yl)benzamide (16n)
4.3.8. (4-Methoxyphenyl)(4-phenyl-2-(phenylamino)thiazol-5-
yl)methanone (16h)
1H NMR (500 MHz, CDCl3) d 3.14 (s, 3H), 7.15 (m, 3H), 7.35 (m,
2H), 7.7 (m, 7H), 8.14–8.17 (m, 2H), 13,30 (s, 1H). IR (KBr cmꢀ1);
3275, 2939, 1674, 1631, 1527, 1472, 1399, 1339, 1240, 1150,
1088, 1027, 954, 900, 837, 746, 649. LC/ESI-MS negative mode
461 ([MꢀH]ꢀ), positive mode 463 ([M+H]+). Mp 270–271 °C. Yield
29%.
1H NMR (500 MHz, DMSO-d6) d 3.71 (s, 3H), 6.72–6.75 (m, 2H),
7.02–7.06 (m, 1H), 7.17–7.24 (m, 3H), 7.34–7.40 (m, 4H), 7.48–
7.51 (m, 2H), 7.65–7.68 (m, 2H), 10.78 (s, 1H). IR (KBr cmꢀ1); 3178,
2950, 1609, 1555, 1520, 1477, 1453, 1425, 1337, 1215, 1168, 1118,
1072, 1025, 912, 854, 760, 713, 665, 639. Elemental Anal. Calcd for
C23H18N2O2S (386.47): C, 71.48; H, 4.69; N, 7.25. Found: C, 71.24;
H, 5.12; N, 7.19. LC/ESI-MS negative mode 385 ([MꢀH]ꢀ), positive
mode 387 ([M+H]+). Mp 185 °C. Yield 39%.
4.3.15. N-(5-Benzoyl-4-phenylthiazol-2-yl)-4-methylbenz-
amide (16o)
1H NMR (500 MHz, DMSO-d6) d 2.39 (s, 3H), 7.17–7.28 (m, 5H),
7.36–7.38 (m, 2H), 7.40–7.45 (m, 3H), 7.57–7.59 (m, 2H), 8.05–8.06
(m, 2H), 13.11 (s, 1H). IR (KBr cmꢀ1); 3333, 2925, 1669, 1624, 1576,
1537, 1474, 1446, 1337, 1299, 1237, 1198, 1166, 1086, 1073, 904,
720, 641. Elemental Anal. Calcd for C24H18N2O2S (398.48): C, 72.34;
H, 4.55; N, 7.03. Found: C, 72.13; H, 4.97; N, 6.98. LC/ESI-MS neg-
ative mode 397 ([MꢀH]ꢀ), positive mode 399 ([M+H]+). Mp 202–
209 °C. Yield 59%.
4.3.9. (4-Phenyl-2-(phenylamino)thiazol-5-yl)(p-toluyl)metha-
none (16i)
1H NMR (500 MHz, DMSO-d6) d 2.22 (s, 3H), 6.99–7.06 (m, 3H),
7.14–7.22 (m, 3H), 7.35–7.40 (m, 6H), 7.65–7.67 (m, 2H) 10.82 (s,
1H). IR (KBr cmꢀ1); 3178, 2920, 1669, 1563, 1519, 1474, 1330,
1220, 1168, 1116, 1021, 914, 861, 787, 748, 704, 668. LC/ESI-MS
negative mode 369 ([MꢀH]ꢀ), positive mode 371 ([M+H]+). Mp
198–199 °C. Yield 34%.
4.3.16. N-(5-(4-Chlorobenzoyl)-4-phenylthiazol-2-yl)-4-methyl-
benzamide (16p)
4.3.10. (4-(Methylsulfonyl)phenyl)(4-phenyl-2-(phenylamino)-
thiazol-5-yl)methanone (16j)
1H NMR (500 MHz, DMSO-d6) d 2.39 (s, 3H), 7.19–7.22 (m, 2H),
7.24–7.30 (m, 3H), 7.36–7.40 (m, 4H), 7.54–7.56 (m, 2H), 8.05–8.06
(m, 2H), 13.14 (s, 1H). IR (KBr cmꢀ1); 3319, 2925, 1655, 1625, 1587,
1540, 1517, 1472, 1402, 1338, 1284, 1197, 1085, 1013, 902, 838,
738, 643. Elemental Anal. Calcd C24H17ClN2O2S (432.92): C,
66.58; H, 3.96; N, 6.47. Found: C, 66.23; H, 4.36; N, 6.40. LC/ESI-
MS negative mode 431 ([MꢀH]ꢀ), positive mode 433 ([M+H]+).
Mp 265–267 °C. Yield 59%.
1H NMR (500 MHz, CDCl3) d 3.1 (s, 3H), 7.0 (m, 3H), 7.2–7.3 (m,
3H), 7.4 (m, 2H), 7.55–7.60 (m, 6H), 11.04 (s, 1H). IR (KBr cmꢀ1);
3275, 2930, 1665, 1541, 1513, 1414, 1340, 1313, 1209, 1148,
1087, 956, 813, 712, 652. LC/ESI-MS negative mode 433 ([MꢀH]ꢀ),
positive mode 435 ([M+H]+). Mp 215 °C. Yield 75%.
4.3.11. N-(5-Benzoyl-4-phenylthiazol-2-yl)benzamide (16k)
1H NMR (500 MHz, DMSO-d6) d 7.18–7.24 (m, 3H), 7.24–7.28
(m, 2H), 7.41–7.46 (m, 3H), 7.56–7.60 (m, 4H), 7.67 (m, 1H), 8.15
(m, 2H), 13.23 (s, 1H). 13C NMR (125 MHz, DMSO-d6) d 125.1,
128.0, 128.3, 128.6, 128.8, 128.9, 129.3, 129.7, 131.6, 132.7,
133.2, 134.4, 137.8, 154.8, 160.7, 166.1, 189.4. IR (KBr cmꢀ1);
3168, 2939, 1668, 1532, 1468, 1330, 1286, 1177, 1072, 936, 871,
799, 694. LC/ESI-MS negative mode 383 ([MꢀH]ꢀ), positive mode
385 ([M+H]+). Mp 205 °C. Yield 48%.
4.3.17. N-(5-Benzoyl-4-phenylthiazol-2-yl)furan-2-carbox-
amide (16q)
1H NMR (500 MHz, DMSO-d6) d 6.76 (m, 1H), 7.15–7.28 (m, 5H),
7.38–7.45 (m, 3H), 7.57 (m, 2H), 7.76 (m, 1H), 8.05 (m, 1H), 13.20
(s, 1H). 13C NMR (125 MHz, DMSO-d6) d 112.6, 117.6, 125.1, 127.9,
128.2, 128.8, 129.2, 129.6, 132.6, 134.3, 137.8, 145.2, 148.0, 154.7,
156.4, 160.1, 189.3. IR (KBr cmꢀ1); 3294, 2934, 1668, 1616, 1530,
1465, 1380, 1332, 1296, 1175, 1098, 1030, 951, 867, 782, 723,
637. LC/ESI-MS negative mode 373 ([MꢀH]ꢀ), positive mode 375
([M+H]+). Mp 190 °C. Yield 41%.
4.3.12. N-(5-(4-Methoxybenzoyl)-4-phenylthiazol-2-
yl)benzamide (16l)
1H NMR (500 MHz, CDCl3) d 3.77 (s, 3H), 6.71 (m, 2H), 7.18 (m,
3H), 7.44 (m, 2H), 7.52 (t, J = 7.72, 2H), 7.62 (t,1H), 7.68 (m, 2H),
7.96 (m, 2H). 13C NMR (125 MHz, CDCl3) d 55.4, 113.4, 126.3,
127.5, 128.2, 128.8, 129.1, 129.3, 130.2, 131.3, 132.1, 133.3,
134.0, 153.1, 159.6, 163.4, 164.7, 188.0. IR (KBr cmꢀ1); 3165,
4.3.18. N-(5-(4-Chlorobenzoyl)-4-phenylthiazol-2-yl)furan-2-
carboxamide (16r)
1H NMR (500 MHz, DMSO-d6) d 6.76 (m, 1H), 7.18–7.22 (m, 2H),
7.26 (m, 1H), 7.27 (m, 2H), 7.37 (m, 2H), 7.54 (m, 2H), 7.78 (m, 1H),
8.06 (m, 1H), 13.20 (s, 1H). 13C NMR (125 MHz, DMSO-d6) d 112.6,