Diisopropylethylamine → Methyl 7-(ethyloxy)-6-[(1-methylethyl)sulfonyl]-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

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Reaction Steps

A solution of methyl 3-(bromomethyl)-7-(ethyloxy)-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (3.5 g, 6.09 mmol), 4-(4-piperidinyl)morpholine (1.778 g, 7.31 mmol), and N,N-diisopropylethylamine (2.13 mL, 12.19 mmol) in acetonitrile (50 mL) was stirred at room temperature for 1.5 h. The solvent was removed under reduced pressure, and the residue was partitioned between a 10% sodium carbonate solution and methylene chloride. The organic phase was separated and washed with Na2CO3. The organic phase was extracted with 2N HCl (three times). The aqueous extracts were cooled in an ice bath and adjusted to pH 12 with 6N NaOH. The precipitated solid was extracted with methylene chloride (three times). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to afford methyl 7-(ethyloxy)-6-[(1-methylethyl)sulfonyl]-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.3 g, 31% yield) as a yellow solid. This material was used without further purification. MS (m/z) 664.2 (M+H+).

Provenance & Evidence