Ethanolamine → N-(2-hydroxyethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-3-[(2,2,3,3-tetramethylcyclopropyl)carbonyl]-1H-indole-5-carboxamide

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Reaction Steps

A mixture 1-(tetrahydro-2H-pyran-4-ylmethyl)-3-[(2,2,3,3-tetramethylcyclopropyl)carbonyl]-1H-indole-5-carboxylic acid (0.10 g, 0.26 mmol, the minor product of Example 114B), 1,1′-carbonyldimidazole (55 mg, 0.34 mmol) and ethanolamine (21 μL, 0.34 mmol) in 4 mL of EtOAc and 3 mL of THF was processed as described in Example 93 to provide the title compound (51 mg, 0.12 mmol, 46% yield). 1H NMR (DMSO-d6, 300 MHz) δ ppm 1.27 (s, 12H), 1.30-1.45 (m, 4H), 2.05-2.19 (m, 1H), 2.23 (s, 1H), 3.22 (dt, J=11.1, 3.2 Hz, 2H), 3.31-3.39 (m, 2H), 3.52 (q, J=6.0 Hz, 2H), 3.83 (d, 2H), 4.17 (d, J=7.1 Hz, 2H), 4.70 (t, J=5.6 Hz, 1H), 7.66 (d, J=8.1 Hz, 1H), 7.74 (dd, J=8.5, 1.7 Hz, 1H), 8.35 (t, J=5.8 Hz, 1H), 8.38 (s, 1H), 8.74 (d, J=1.4 Hz, 1H); MS (DCI/NH3) m/z 427 (M+H)+; Anal. Calculated for C25H34N2O4.0.3H2O: C, 69.51; H, 8.07; N, 6.49. Found: C, 69.36; H, 7.88; N, 6.27.

Provenance & Evidence