Acetic Anhydride → 2-(3-(((3S)-1-acetyl-3-piperidinyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one

Participants

Reaction Conditions

Reaction Steps

Prepared according to Example 50, using TEA (37.7 μl, 0.271 mmol, Sigma Aldrich), (S)-2-(2-methyl-3-(piperidin-3-ylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Ex. 76, 85 mg, 0.226 mmol), Ac2O (42.6 μl, 0.452 mmol), and DCM (2.3 mL) and stirring at 25° C. for 1 h. Purification by concentration of the reaction solution, solubilization in MeOH, and filtration through a pre-washed column of Si-carbonate (SiliaPrep, Silicyle) provided 2-(3-(((3S)-1-acetyl-3-piperidinyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (28 mg, 30%). 1H NMR (DMSO-d6) δ: 7.85-7.91 (m, 1H), 7.77-7.83 (m, 1H), 7.54-7.63 (m, 2H), 7.30-7.40 (m, 2H), 7.05-7.11 (m, 1H), 4.45-4.55 (m, 1H), 4.27-4.39 (m, 1H), 4.13-4.27 (m, 1H), 3.96-4.10 (m, 1H), 3.86-3.95 (m, 1H), 3.76-3.86 (m, 1H), 3.39-3.46 (m, 3H), 2.87-2.97 (m, 1H), 2.01-2.07 (m, 3H), 1.59 (s, 3H), 1.10-1.22 (m, 3H). m/z (ESI, +ve) 419.1 (M+H)+.

Provenance & Evidence