Dimethylamine → N,N-dimethyl-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 dimethylamine (2 M solution in THF, 0.17 mL, 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 (38 mg, 0.093 mmol, 35% yield). 1H NMR (DMSO-d6, 300 MHz) δ ppm 1.25 (s, 6H), 1.27 (s, 6H), 1.29-1.48 (m, 4H), 2.03-2.18 (m, 1H), 2.20 (s, 1H), 2.97 (s, 6H), 3.23 (dt, J=11.3, 2.9 Hz, 2H), 3.78-3.89 (m, 2H), 4.17 (d, J=7.1 Hz, 2H), 7.27 (dd, J=8.5, 1.7 Hz, 1H), 7.66 (d, J=9.2 Hz, 1H), 8.27 (d, J=1.4 Hz, 1H), 8.37 (s, 1H); MS (DCI/NH3) m/z 411 (M+H)+; Anal. Calculated for C25H34N2O3.0.2H2O: C, 72.50; H, 8.37; N, 6.76. Found: C, 72.51; H, 8.29; N, 6.66.

Provenance & Evidence