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Brands, K. M. J.; Payack, J. F.; Rosen, J. D.; Nelson, T. D.; Candelario, A.; Huffman, M. A.; Zhao, M. M.; Li, J.; Craig, B.; Song, Z. J.; Tschaen, D. M.; Hansen, K.; Devine, P. N.; Pye, P. J.; Rossen, K.; Dormer, P. G.; Reamer, R. A.; Welch, C. J.; Mathre, D. J.; Tsou, N. N.; McNamara, J. M.; Reider, P. J. J. Am. Chem. Soc. 2003, 125, 2129-2135 and references therein.
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(a) Kramer, M. S.; Cutler, N.; Feighner, J.; Shrivastava, R.; Carman, J.; Sramek, J. J.; Reines, S. A.; Guanghan, L.; Snavely, D.; Wyatt-Knowles, E.; Hale, J. J.; Mills, S. G.; MacCoss, M.; Swain, C. J.; Harrison, T.; Hill, R. A.; Hefti, F.; Scolnick, E. M.; Cascieri, M. A.; Chicchi, G. G.; Sadowski, S.; Williams, A. R.; Hewson, L.; Smith, D.; Carlson, E. J.; Hargreaves, R. J.; Rupniak, N. M. J. Science 1998, 281, 1640.
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Cascieri, M.A.19
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Sadowski, S.21
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Hewson, L.23
Smith, D.24
Carlson, E.J.25
Hargreaves, R.J.26
Rupniak, N.M.J.27
more..
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8
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(c) Hale, J. J.; Mills, S. G.; MacCoss, M.; Shah, S. K.; Qi, H.; Mathre, D. J.; Cascieri, M. A.; Sadowski, C. D.; MacIntyre, D. E.; Metzger, J. M. J. Med. Chem. 1996, 39, 1760.
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9
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(d) Hale, J. J.; Mill, S. G.; MacCoss, M.; Finke, P. E.; Cascieri, M. A.; Sadowski, S.; Ber, E.; Chicchi, G. G.; Kurtz, M.; Metzger, J.; Eiermann, G.; Tsou, N. N.; Tattersall, D.; Rupniak, N. M. J.; Williams, A. R.; Rycroft, W.; Hargreaves, R.; MacIntyre, D. E. J. Med. Chem. 1998, 41, 4607.
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(e) Hale, J. J.; Mills, S. G.; MacCoss, M.; Dorn, C. P.; Finke, P. E.; Budhu, R. J.; Reamer, R. A.; Huskey, S.-E. W.; Luffer-Atlas, D.; Dean. B. J.; McGowan, E. M.; Feeney, W. P.; Chiu, S.-H. L.; Cascieri, M. A.; Chicchi, G. G.; Kurtz, M. M.; Sadowski, S.; Ber, E.; Tattersall, D.; Rupniak, N. M. J.; Williams, A. R.; Rycroft, W.; Hargreaves, R.; Metzger, J. M.; MacIntyre, D. E. J. Med. Chem. 2000, 43, 1234.
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more..
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0035935713
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Harrison, T.; Owens, A. P.; Williams, B. J.; Swain, C. J.; Williams, A.; Carlson, E. J.; Rycroft, W.; Tattersall, F. D.; Cascieri, M. A.; Chicchi, G. G.; Sadowski, S.; Rupniak, N. M. J.; Hargreaves, R. J. J. Med. Chem. 2001, 44, 4296.
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Hargreaves, R.J.13
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12
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23044487497
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Larsen, R.D.3
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0001621204
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Ishihara, K.1
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16
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0023894194
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(a) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616-1623.
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Mikami, K.1
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22
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0001463438
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(a) For instance, using N-formylmorpholine, 3-phenylpropynal was synthesized from lithium phenyl acetylide in 80% yield: Olah, G. A.; Ohannesian, L.; Arvanaghi, M. J. Org. Chem. 1984, 49, 3856-3857.
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84982697581
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Olah, G.A.1
Arvanaghi, M.2
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27
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23044452708
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note
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All Michael adducts have a strong absorption at 325 nm.
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28
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23044503562
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note
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Under the conditions we used for the reductive animation of triazole aldehyde 9 with borane dimethylamine, aldehyde 14 was reduced to the corresponding hydroxymethyl derivative 15.
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30
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0032171542
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Journet, M.; Cai, D.; DiMichele, L. M.; Larsen, R. D. Tetrahedron Lett. 1998, 39, 6427-6428.
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Journet, M.1
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DiMichele, L.M.3
Larsen, R.D.4
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32
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23044431923
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note
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In the absence of sodium azide, the anion of triazole aldehyde 8 may react with acetylenic aldehyde 4 as observed with 7.
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33
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23044445067
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U.S. Patent 6,051,717, 2000
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Cai, D.; Journet, M.; Kowal, J.; Larsen, R. D. U.S. Patent 6,051,717, 2000.
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Cai, D.1
Journet, M.2
Kowal, J.3
Larsen, R.D.4
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34
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0035944976
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Journet, M.; Cai, D.; Kowal, J. J.; Larsen, R. D. Tetrahedron Lett. 2001, 42, 9117-9117.
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Journet, M.1
Cai, D.2
Kowal, J.J.3
Larsen, R.D.4
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35
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23044507892
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note
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4) to 30/70 in 20 min. Retention time for azide was 7.35 min.
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36
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23044444628
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note
-
Triazole aldehyde 3 is highly water soluble. Its solubility is 63 g/L in methanol and DMSO, 19 g/L in DMF and <4 g/L in 2-propanol, 2-butanol, chloroform, THF, and toluene.
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38
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23044463228
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note
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4 into a cold (0°C) solution of acetic acid (3.3 equiv) in DMAC will control the foaming caused by the release of hydrogen gas.
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