Hydrochloric Acid → HCID 89784358, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-methyl-2-(methylthio)-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinazolin-4(3H)-one (34.0 mg, 0.100 mmol), aniline (0.5 mL, 5.49 mmol), and HCl (conc.) (20 μl, 0.240 mmol) was heated by microwave in a sealed flask at 150° C. for 10 min. The mixture was diluted with Et2O (5 mL) and the precipitated solid was collected by vacuum filtration, washed with Et2O (5 mL), and dried in vacuo. Purification of the residue by revered-phase HPLC (Phenomenex Gemini C18 column (150×30 mm, 10 μm), 35 mL/min, 5-100% ACN/H2O+0.1% TFA) followed by supercritical-fluid chromatography (Chiralcel OD-H (250×21 mm, 5 μm), 50% liquid CO2/50% MeOH, 55 mL/min) afforded 3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-2-(phenylamino)quinazolin-4(3H)-one (1.6 mg, 4.15 μmol) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.98-9.15 (1H, m), 7.95-8.04 (1H, m), 7.81 (1H, d, J=7.6 Hz), 7.41-7.53 (5H, m), 7.23-7.33 (1H, m), 7.08-7.18 (1H, m), 6.89 (1H, s), 6.82 (1H, s), 3.61 (3H, s), 3.28 (2H, obsc. m), 2.33 (2H, m). m/z (ESI, +ve) 386.1 (M+H)+.

Provenance & Evidence