Diisopropylethylamine → methyl 2-methyl-2-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)amino)propanoate

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Reaction Conditions

Reaction Steps

Prepared according to Example 131, using DIPEA (1761 μl, 10.12 mmol), aminoisobutyric acid methyl ester hydrochloride (778 mg, 5.06 mmol, Sigma Aldrich), and 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 500 mg, 1.687 mmol) in DMSO (8437 μl) stirring at 95° C. for 2 h. Purification by column chromatography (silica gel: 0 to 10% MeOH/DCM) provided methyl 2-methyl-2-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)amino)propanoate (557 mg, 81%). 1H NMR (CDCl3) δ: 11.16-11.25 (m, 1H), 7.96-8.01 (m, 1H), 7.69-7.74 (m, 1H), 7.40-7.46 (m, 1H), 7.08-7.12 (m, 1H), 5.56-5.71 (m, 1H), 5.15-5.20 (m, 1H), 3.66-3.73 (m, 2H), 3.56 (s, 3H), 3.25 (s, 2H), 2.65 (s, 3H), 1.79 (s, 6H). m/z (ESI, +ve) 394.1 (M+H)+.

Provenance & Evidence