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H. Pingali et al. / Bioorg. Med. Chem. 16 (2008) 7117–7127
3.52 (t, J = 10.7 Hz, 2H), 3.89–3.93 (dd, J = 12.6 and 4.2 Hz, 2H), 4.20
(t, J = 6.7 Hz, 2H), 6.81 (d, J = 8.5 Hz, 2H), 6.95 (d, J = 8.5 Hz, 2H),
7.23 (d, J = 8.3 Hz, 2H), 7.85 (d, J = 8.1 Hz, 2H); 13C NMR (DMSO-
d6): d 9.78, 20.94, 25.51, 32.84, 34.88, 66.08, 67.01, 97.56, 114.33,
124.56, 125.41, 129.60, 129.97, 130.26, 132.50, 139.76, 144.59,
156.65, 158.54, 171.32; ESI-MS m/z: 452.2 (M+H)+.
6.3.37. c-5-[4-{2-(2-tert-Butyl-5-methyloxazol-4-yl)ethoxy}
benzyl]-2-methyl-1, 3-dioxane-r-2-carboxylic acid (13i)
This compound was prepared from 12i by means of a procedure
similar to that reported for 13a. Off-white solid; yield: 60%; mp:
140–141 °C; purity by HPLC: 98%; IR (KBr): 2960, 2923, 1718,
1514, 1249, 1120, and 767 cmꢂ1 1H NMR (CDCl3): d 1.35 (s, 9H),
;
1.54 (s, 3H), 2.24 (s, 3H), 2.27 (s, 3H), 2.89–2.96 (dd, J = 15.0 and
8.1 Hz, 2H), 3.50 (t, J = 9.5 Hz, 2H), 3.84–3.89 (m, 2H), 4.12 (t,
J = 6.7 Hz, 2H), 6.78 (d, J = 8.3 Hz, 2H), 6.92 (d, J = 8.1 Hz, 2H); 13C
NMR (100 MHz, DMSO-d6): d 10.45, 25.84, 28.83, 33.69, 33.86,
34.87, 61.43, 68.10, 98.24, 114.97, 129.39, 129.64, 130.66, 146.63,
157.28, 170.17, 173.09; ESI-MS m/z: 418.1 (M+H)+.
6.3.33. 2-Methyl-c-5-{4-[3-(5-methyl-2-(4-methylphenyl)
oxazol-4-yl)propoxy]benzyl}-1,3-dioxane-r-2-carboxylic acid
(13e)
This compound was prepared from 12e by means of a procedure
similar to that reported for 13a. White solid; yield: 73%; mp: 126–
128 °C; purity by HPLC: 97%; IR (KBr): 2922, 1716, 1556, 1469,
1244, 1215, 1120, and 1035 cmꢂ1 1H NMR (CDCl3): d 1.56 (s,
;
Acknowledgements
3H), 2.05–2.15 (m, 2H), 2.27–2.29 (m, 6H), 2.38 (s, 3H), 2.72 (t,
J = 7.2 Hz, 2H), 3.55 (t, J = 10.8 Hz, 2H), 3.89-3.97 (m, 4H), 6.80 (d,
J = 8.5 Hz, 2H), 6.98 (d, J = 8.5 Hz, 2H), 7.22–7.26 (m, 2H), 7.84 (d,
J = 8.2 Hz, 2H); 13C NMR (DMSO-d6): d 9.62, 20.93, 21.42, 25.53,
27.98, 32.87, 34.89, 66.33, 67.09, 97.56, 114.29, 124.65, 125.38,
129.52, 130.12, 134.89, 139.66, 143.39, 157.02, 158.50, 171.31;
ESI-MS m/z: 466.2 (M+H)+.
Authors are grateful to Dr. B. B. Lohray, Dr. V. B. Lohray for valu-
able suggestions, management of Zydus Group for encouragement,
and the analytical department for support.
References and notes
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This compound was prepared from 12f by means of a procedure
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172–173 °C; purity by HPLC: 99%; IR (KBr): 2923, 1718, 1508,
1259, 1224, and 1122 cmꢂ1 1H NMR (CDCl3): d 1.54 (s, 3H),
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2.21–2.28 (m, 3H), 2.39 (s, 3H), 2.52 (s, 3H), 3.49 (t, J = 11.1 Hz,
2H), 3.89–3.93 (dd, J = 12.6 and 4.2 Hz, 2H), 4.96 (s, 2H), 6.75 (d,
J = 2.8 Hz, 1H), 6.91 (d, J = 8.6 Hz, 2H), 7.00 (d, J = 8.5 Hz, 2H),
7.48 (d, J = 3.6 Hz, 1H); 13C NMR (DMSO-d6): d 9.86, 14.95, 25.53,
32.89, 34.86, 61.23, 67.08, 97.56, 114.64, 126.74, 127.54, 129.62,
130.61, 131.68, 142.95, 146.49, 155.13, 156.61, 171.31; ESI-MS
m/z: 444.2 (M+H)+.
6.3.35. 2-Methyl-c-5-{4-[2-(5-methyl-2-(5-methylthiophen-2-yl)
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This compound was prepared from 12g by means of a proce-
dure similar to that reported for 13a. Off-white solid; yield: 46%;
mp: 122–124 °C; purity by HPLC: 96%; IR (KBr): 2922, 1718,
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;
2.20–2.26 (m, 3H), 2.34 (s, 3H), 2.51 (s, 3H), 2.95–2.97 (t,
J = 6.7 Hz, 2H), 3.5 (t, J = 10.7 Hz, 2H), 3.90 (d, J = 9.9 Hz, 2H),
4.18 (t, J = 6.3 Hz, 2H), 6.73 (d, J = 2.8 Hz, 1H), 6.80 (d,
J = 8.2 Hz, 2H), 6.95 (d, J = 8.0 Hz, 2H), 7.42 (d, J = 3.6 Hz, 1H);
13C NMR (DMSO-d6): d 9.71, 14.93, 25.55, 32.90, 34.89, 66.01,
67.10, 97.58, 114.33, 126.72, 127.01, 127.20, 129.60, 130.27,
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6.3.36. c-5-[4-(2-tert-Butyl-5-methyloxazol-4-ylmethoxy)
benzyl]-2-methyl-1,3-dioxane-r-2-carboxylic acid (13h)
This compound was prepared from 12h by means of a proce-
dure similar to that reported for 13a. White solid; yield: 49%;
mp: 117–118 °C; purity by HPLC: 99%; IR (KBr): 2968, 1735,
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1514, 1217, 1120, and 1029 cmꢂ1 1H NMR (CDCl3): d 1.38 (s,
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Seethala, R.; Cheng, L.; Sleph, P.; Sun, W.; Tieman, A.; Wetterau, J. R.; Doweyko,
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2248.
9H), 1.51 (s, 3H), 2.12 (d, J = 7.2 Hz, 2H), 2.22–2.26 (m, 1H), 2.33
(s, 3H), 3.43 (t, J = 11.3 Hz, 2H), 3.72–3.80 (dd, J = 11.8 and 4.1 Hz,
2H), 4.90 (s, 2H), 6.82 (d, J = 8.3 Hz, 2H), 6.91 (d, J = 8.7 Hz, 2H);
13C NMR (DMSO-d6): d 10.35, 25.84, 28.53, 33.69, 33.86, 34.77,
61.63, 68.10, 98.24, 114.97, 129.39, 129.64, 130.66, 146.63,
157.28, 170.17, 173.09; ESI-MS m/z: 404.1 (M+H)+.
32. Nissen, S. E.; Wolski, K.; Topol, E. J. JAMA 2005, 294, 2581.