Ethanolamine → (S)-N-{3-Cyclohexyl-1-[2-(7-fluoro-2,3-dihydro-indol-1-yl)-ethylcarbamoyl]-propyl}-3-methoxy-benzamide

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Following the procedures of Example 3, except using m-anisoyl chloride, (S)-2-amino-4-cyclohexyl-butyric acid, ethanolamine and 7-fluoroindoline as starting materials, the title compound was prepared in 40% yield. The final material was purified by reverse phase preparative HPLC using TFA as a modifier. The final compound is therefore a partial TFA salt and the properties are reported for the material as it appeared after solvent removal: 1H NMR (CDCl3, 400 MHz) δ 0.73-0.87 (m, 2H), 1.03-1.28 (m, 6H), 1.58-1.78 (m, 6H), 1.83-1.95 (m, 1H), 3.01 (dd, 2H, J1=J2=8.4), 3.41-3.50 (m, 4H), 3.55-3.72 (m, 1H), 3.84 (s, 3H), 4.63 (dd, 1H, J1=7.1, J2=14.3), 6.53-6.68 (m, 2H), 6.78 (dd, 1H, J1=8.5, J2=12.3), 6.86 (d, 1H, J1=7.0), 7.01-7.08 (m, 2H), 7.20 (d, 1H, J1=7.8), 7.26-7.39 (m, 3H); HPLC-MS calcd. for C28H36FN3O3 (M+H+) 482.3, found 482.5.

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