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

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Reaction Steps

To a solution of sodium salt of 4-(4-fluorophenyl)-1-methyl-1H-indole-6-carboxylic acid (25.0 mg, 56.0 μmol), hydrochloride salt of (1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (16.4 mg, 67.0 μmol) and N-methylmorpholine (30.9 μL, 0.28 mmol) in N,N-dimethylformamide (0.56 mL) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (18.9 mg, 98.0 μmol), 1-hydroxy-7-azabenzotriazole (3.8 mg, 28.1 μmol). The mixture was stirred at ambient temperature. After 18 h, the mixture was concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% NH4OH) gave the title compound (22.1 mg): HRMS [M+1] found=458.1491; 1H NMR (400 MHz, DMSO): δ 8.90 (d, J=7.3 Hz, 1H); 8.53 (s, 1H); 8.06 (s, 1H); 7.94 (d, J=8.4 Hz, 1H); 7.74 (dd, =8.4, 5.5 Hz, 2H); 7.69 (s, 1H); 7.59 (d, J=3.1 Hz, 1H); 7.55 (d, J=8.4 Hz, 1H); 7.40-7.31 (m, 2H); 6.56 (d, J=3.1 Hz, 1H); 5.27-5.18 (m, 1H); 3.90 (s, 3H); 1.56 (d, J=7.1 Hz, 3H).

Provenance & Evidence