212
H. Xie et al. / European Journal of Medicinal Chemistry 52 (2012) 205e212
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J ¼ 7.6 Hz), 5.51 (2H, AB q, J ¼ 35.2 Hz, 15.6 Hz), 3.61e3.58 (1H, m),
3.43e3.39 (1H, m), 3.17e3.11 (2H, m), 2.91e2.85 (1H, m), 2.09e2.07
(1H, m), 1.84e1.81 (1H, m), 1.75e1.70 (1H, m), 1.61e1.58 (1H, m). 13C
NMR (125 MHz, MeOD)
d ppm: 23.44 (1C), 28.99 (1C), 35.29 (1C),
47.40 (1C), 53.04 (1C), 53.81 (1C), 111.77 (1C), 112.65 (1C), 118.36
(1C), 119.08 (1C), 122.75 (1C), 128.97 (1C), 129.14 (1C), 132.04 (1C),
134.23 (2C),134.40 (2C),141.69 (1C),142.07 (1C),143.37 (1C),153.50
(1C), 156.44 (1C), 157.00 (1C). ESI-MS calculated for (C24H23N7O)
[M þ H]þ, 426.2, found 426.2.
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Discovery of alogliptin:
a potent, selective, bioavailable, and efficacious
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aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-
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long-acting, and orally bioavailable DPP-4 inhibitor for the treatment of type 2
diabetes, J. Med. Chem. 50 (2007) 6450e6453.
5.14. 2-((2-((R)-3-Aminopiperidin-1-yl)-4-oxo-7-(thiophen-3-yl)-
4H-pyrrolo[3,2-d]pyrimidin-3(5H)-yl) methyl)benzonitrile (21m)
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[20] A. Orita, D. Hasegawa, T. Nakano, J. Otera, Double elimination protocol for
Yellow powder. Yield: 38.6%. 1H NMR (400 MHz, DMSO-d6)
d
ppm: 7.98 (1H, s), 7.82e7.78 (2H, m), 7.69 (1H, d, J ¼ 4.0 Hz),
7.61e7.55 (3H, m), 7.06 (1H, d, J ¼ 8.0 Hz), 5.46 (2H, AB q,
J ¼ 50.4 Hz, 15.6 Hz), 3.46e3.43 (1H, m), 3.36e3.33 (1H, m),
3.11e3.05 (2H, m), 2.90e2.75 (1H, m), 2.02e1.92 (1H, m), 1.88e1.76
(1H, m), 1.66e1.46 (2H, m). 13C NMR (125 MHz, DMSO-d6)
d ppm:
30.00 (1C), 35.43 (1C), 46.66 (1C), 47.69 (1C), 52.56 (1C), 53.21 (1C),
110.76 (1C), 113.58 (1C), 116.58 (1C), 118.56 (1C), 126.67 (1C), 127.09
(1C), 128.84 (1C), 129.11 (1C), 129.93 (1C), 130.02 (1C), 134.20 (1C),
134.52 (1C), 134.59 (1C), 140.49 (1C), 142.27 (1C), 154.90 (1C),
155.90 (1C). ESI-MS calculated for (C23H22N6OS) [M þ H]þ, 431.2,
found 431.2.
Acknowledgements
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8
This research was supported by Natural Science Foundation of
Guangdong Province, China (10251066302000000) and the Natural
Science Foundation of China (NSFC 21102145).
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Appendix A. Supplementary material
Supplementary material associated with this article can be
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