4-Methylmorpholine → 3-(2-Chlorophenyl)-1-(4-methylphenyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}-1H-indole-6-carboxamide

Participants

Reaction Steps

To a solution of 3-(2-chlorophenyl)-1-(4-methylphenyl)-1H-indole-6-carboxylic acid (9.5 mg, 26.0 μmol) in N,N-dimethylformamide (0.5 mL) were added hydrochloride salt of (1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (7.3 mg, 30.0 μmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (12.5 mg, 65.0 μmol), 1-hydroxy-7-azabenzotriazole (2.2 mg, 16.0 μmol) and N-methylmorpholine (12.0 μL, 0.11 mmol). The mixture was stirred at ambient temperature for 30 min. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the bistrifluoroacetate salt of the title compound (9.7 mg): HRMS [M+1] found=550.1505; 1H NMR (500 MHz, CDCl3): δ 8.50 (s, 1H); 8.08 (s, 1H); 7.67 (t, J=7.7 Hz, 3H); 7.61-7.47 (m, 4H); 7.44-7.21 (m, 6H); 6.66 (d, J=6.6 Hz, 1H); 5.31-5.23 (m, 1H); 2.44 (s, 3H); 1.64 (dd, J=20.9, 7.1 Hz, 3H).

Provenance & Evidence