Ethanolamine → (S)-N-{3-Cyclohexyl-1-[2-(5-cyano-2,3-dihydro-indol-1-yl)-ethylcarbamoyl]-propyl}-3-methoxy-benzamide

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Reaction Steps

Following the procedures of Example 3, except using m-anisoyl chloride, (S)-2-amino-4-cyclohexyl-butyric acid, ethanolamine and 5-cyanoindoline as starting materials, the title compound was prepared in 20% 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 0.64-0.77 (m, 2H), 0.97-1.15 (m, 6H), 1.49-1.64 (m, 6H), 1.72-1.84 (m, 1H), 2.84-2.92 (m, 2H), 3.16-3.30 (m, 2H), 3.32-3.51 (m, 4H), 3.77 (s, 3H), 4.49 (dd, 1H, J1=7.4, J2=14.4), 6.24 (d, 1H, J1=8.3), 6.97-7.02 (m, 1H), 7.04-7.07 (m, 1H), 7.09-7.15 (m, 2H), 7.18-7.28 (m, 2H); HPLC-MS calcd. for C29H36N4O3 (M+H+) 482.3, found 482.5.

Provenance & Evidence