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(b) Alternatively, reaction of AM resin with CDI followed by hydrazine afforded 1.
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1-argininal urokinase inhibitors was recently disclosed by Corvas: Weinhouse, M. I.; Roberts, C.; Cohen, C. R.; Bradbury, A. E.; Ma, M. G.; Dixon, S. A.; Nolan, T. G.; Tamura, S. Y.; Brunck, T. K. 217th National American Chemical Society Meeting, Anaheim, CA, March 21-25, 1999; MEDI.090.
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0039476553
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note
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All new intermediates were characterized by full spectroscopic (IR, NMR, low/high resolution MS) data. Yields refer to spectroscopically and chromatographically homogeneous (≥95% by HPLC, TLC) materials.
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0014772602
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0025834386
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Semple, J. E.; Rowley, D. C.; Brunck, T. K.; Uong, T. H.; Minami, N. K.; Owens, T. D.; Tamura, S. Y.; Goldman, E. A.; Siev, D. V.; Ardecky, R. J.; Carpenter, S. H.; Ge, Y.; Richard, B. M.; Nolan, T. G.; Håkanson, K.; Tulinsky, A.; Nutt, R. F.; Ripka, W. C. J. Med. Chem. 1996, 39, 4531.
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Ripka, W.C.18
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44
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0039476551
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note
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2O (9/1) (1.5 mL) was added to the elaborated resin (100 mg) in a Whatman minicolumn. The mixture was allowed to shake for 1 h at ambient temperature. The filtrate was collected and adjusted to pH = 3 with 6 M ammonium acetate (∼1.5 mL), and the resulting solution was purified through a miniprep RP-HPLC column. The combined fractions were lyophilized to afford the desired targets 3a-h as colorless, amorphous solids, which were stored at 0-4°C under a nitrogen atmosphere.
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