1,2-Dichloroethane → HCID 53476908, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(methylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.200 g, 0.346 mmol), (1S)-1-phenylethanamine (0.063 g, 0.519 mmol), EDC (0.266 g, 1.39 mmol), HOBT (0.053 g, 0.346 mmol) and N,N-diisopropylethylamine (0.605 mL, 3.46 mmol) in N,N-dimethylformamide (2 mL) and tetrahydrofuran (2 mL) was heated to 50° C. overnight. The solvent was removed under reduced pressure, and the residue was dissolved in DMSO and purified via HPLC (Waters, Sunfire, 30×75 mm column, 50 mL/min, 20-60% MeCN/H2O with 0.1% TFA). The fractions containing the product were neutralized with saturated aqueous NaHCO3 and extracted with methylene chloride (three times). The combined organic extracts were washed with brine (two times), dried over Na2SO4, filtered, and concentrated to afford 6-(methylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-N-[(1S)-1-phenylethyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxamide (0.116 g, 47% yield). MS (m/z) 681.3 (M+H+).

Provenance & Evidence