tert-butyl (3R)-3-aminopiperidine-1-carboxylate → tert-butyl (3R)-3-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-2-quinoxalinyl)amino)-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

Prepared according to Example 131, using (R)-3-amino-1-boc-piperidine (180 μL, 0.759 mmol, CNH Technologies, Inc., Woburn, Mass.), 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 75 mg, 0.253 mmol), and DMSO (2.5 mL) and stirring at 100° C. for 2 h. Purification by column chromatography (silica gel: 0.5 to 10% MeOH/DCM) and reverse phase chromatography (Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in ACN/H2O, gradient 5% to 95%) provided tert-butyl (3R)-3-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-2-quinoxalinyl)amino)-1-piperidinecarboxylate (1.2 mg, 1.0%) as the free base after washing with saturated aq. NaHCO3, extracting with 10% MeOH/DCM, drying over Na2SO4, and concentrating under reduced pressure. 1H NMR (CDCl3) δ: 12.37-12.47 (m, 1H), 7.93-7.98 (m, 1H), 7.66-7.71 (m, 1H), 7.37-7.44 (m, 1H), 7.11-7.16 (m, 1H), 5.43-5.49 (m, 1H), 4.10-4.19 (m, 2H), 3.63-3.70 (m, 4H), 2.93-3.00 (m, 3H), 2.57-2.60 (m, 3H), 2.04-2.06 (m, 2H), 1.78-1.91 (m, 3H), 1.59-1.77 (m, 9H). m/z (ESI, +ve) 477.2 (M+H)+.

Provenance & Evidence