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3 Agonists. U.S. Patent 5776983, 7/7/98.
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Bisacchi, G.S.7
Gavai, A.V.8
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2-Hydroxy-3-(4-hydroxy-3-sulfonamidophenyl)propylamines Useful as Beta 3 Adrenergic Agonists. U.S. Patent 6436914, 8/20/2002
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Boston, MA, 8/23-27/98, MEDI 24
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A portion of this work has been presented. Sher, P. M.; Gavai, A. V.; Bisacchi, G.; Mikkilineni, A. B.; Poss, K. M.; Cai, Z.-W.; Fisher, L. G.; McCann, P. J.; Girotra, R. N.; Wu, G.; Merchant, Z.; Kocy, O.; Bednarz, M. S.; Slusarchyk, D. A.; Skwish, S.; Allen, G. T.; Hillyer, D.; Frohlich, E. B. H.; Abboa-Offei, B. E.; Cap, M.; Waldron, T. L.; George, R. J.; Tesfamariam, B.; Ciosek, C. P., Jr.; Young, D. A.; Dickinson, K. E.; Seymour, A. A.; Arbeeny, C. M.; Washburn, W. N. Beta 3 Adrenoceptor Agonists Part III: Functional Selectivity Optimization Using Solid Phase Parallel Array Synthesis. From BMS-196085 To BMS-210285. 216th American Chemical Society National Meeting, Boston, MA, 8/23-27/98, MEDI 24.
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Sher, P.M.1
Gavai, A.V.2
Bisacchi, G.3
Mikkilineni, A.B.4
Poss, K.M.5
Cai, Z.-W.6
Fisher, L.G.7
McCann, P.J.8
Girotra, R.N.9
Wu, G.10
Merchant, Z.11
Kocy, O.12
Bednarz, M.S.13
Slusarchyk, D.A.14
Skwish, S.15
Allen, G.T.16
Hillyer, D.17
Frohlich, E.B.H.18
Abboa-Offei, B.E.19
Cap, M.20
Waldron, T.L.21
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Tesfamariam, B.23
Ciosek Jr., C.P.24
Young, D.A.25
Dickinson, K.E.26
Seymour, A.A.27
Arbeeny, C.M.28
Washburn, W.N.29
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22
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33751499264
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Grignard reagents used were commercially available as either THF or ether solutions, or in most cases, were prepared in ether using "dry- stirred" magnesium according to Baker, K. V.; Brown, J. M.; Hughes, N.; Skarnulis, A. J.; Sexton, A. J. Org. Chem. 1991, 56, 698-703.
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24
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13544259713
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note
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Small scale separation of diastereomers could be accomplished in about half of the cases attempted by preparative HPLC using a porous graphite Hypercarb column. See Experimental Section, Separation of Diastereomers 3x.
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25
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33748112928
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13544255552
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note
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11 not only deprotonated the methyl group in THF at room temperature, as shown by deuterium quenching, but also added to the imine and cleaved the difluoromethoxy group to generate a phenol.
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28
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13544269391
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note
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1a,c As described herein, similar ratios were produced in reactions of similar resin-bound imines with benzylic Grignard reagents.
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29
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13544265447
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note
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1a,c,d See also Separation of Diastereomers 3x in the Experimental Section.
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13544273962
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U.S. Patent 3914318
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2 in a mixture of 30% aqueous KOH, 2-propanol, and tetrabutylammonium bromide at 80°C; see also U.S. Patent 4316989.
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13544250615
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U.S. Patent 4316989
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2 in a mixture of 30% aqueous KOH, 2-propanol, and tetrabutylammonium bromide at 80°C; see also U.S. Patent 4316989.
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