Potassium Carbonate → ethyl 2-(((tert-butoxycarbonyl)amino)methyl)-5-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate

Participants

Reaction Steps

This compound (0.25 g, 35% yield) as a yellow solid was prepared according to the procedures described for Intermediate 355b, using 4-((tert-butoxycarbonyl)amino)-3-oxobutanoate (601) (0.45 g, 1.84 mmol), K2CO3 (0.53 g, 3.83 mmol), 2-bromo-1-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)ethanone (613) (0.49 g, 1.53 mmol) in DMF (4 mL) as starting material, followed by subsequent treatment of ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxobutanoate (363a: m/z (ESI, +ve) 485.1 (M+H)+) with NH4OAc (0.36 g, 4.6 mmol) in EtOH (6 mL) and AcOH (1.5 mL). 1H NMR (400 MHz, DMSO-d6) δ 12.56 (br. s., 1H), 7.60 (dd, J=0.98, 8.02 Hz, 1H), 7.54 (d, J=1.96 Hz, 1H), 7.31-7.39 (m, 2H), 7.06 (br. s., 1H), 4.50 (d, J=5.48 Hz, 2H), 4.22 (q, J=7.04 Hz, 2H), 3.03 (br. s., 1H), 2.49 (s, 3H), 1.38 (s, 9H), 1.30 (t, J=7.04 Hz, 3H), 0.96-1.02 (m, 2H), 0.62-0.69 (m, 2H). m/z (ESI, +ve) 466.2 (M+H)+.

Provenance & Evidence