Potassium Carbonate → ethyl 2-(((tert-butoxycarbonyl)amino)methyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylate

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Reaction Steps

This compound (380 mg, 0.75 mmol, 55% yield) as a yellow solid was prepared according to the procedure described for 293b, using 2-bromo-1-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)ethanone (616) (492 mg, 1.36 mmol), ethyl 4-((tert-butoxycarbonyl)amino)-3-oxobutanoate (601) (400 mg, 1.63 mmol) and K2CO3 (0.21 mL, 3.40 mmol) in DMF (2.75 mL), followed by subsequent treatment of the resulting ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-2-oxoethyl)-3-oxobutanoate (301a) (530 mg, m/z (ESI, +ve) 527.2 (M+H)+) with NH4OAc (838 mg, 10.87 mmol) in 2 mL of EtOH and AcOH (1 mL) at 60° C. overnight. 1H NMR (400 MHz, CDCl3) δ ppm 7.92-7.98 (m, 1H), 7.68-7.74 (m, 1H), 7.44 (t, J=7.92 Hz, 1H), 7.11 (d, J=2.74 Hz, 1H), 5.44 (br. s., 1H), 5.18 (t, J=6.26 Hz, 1H), 4.56-4.65 (m, 2H), 4.54 (d, J=6.46 Hz, 2H), 4.33 (q, J=7.17 Hz, 2H), 2.63 (s, 3H), 1.35-1.43 (m, 12H). 19F NMR (376 MHz, CDCl3) δ ppm −70.89 (s, 3F). m/z (ESI, +ve) 508.1 (M+H)+.

Provenance & Evidence