Pyridine → 2-(1-adamantyl)-N-(2-isopropyl-4-oxoquinazolin-3(4H)-yl)acetamide

Participants

Reaction Steps

3-Amino-2-isopropyl-4(3H)-quinazolinone (Aldrich, 97.5 mg, 0.48 mmol) was dissolved in chloroform (5 mL). 1-Adamantaneacetyl chloride (107.0 mg, 0.50 mmol) and pyridine (100 μL, 1.24 mmol) were added, and the reaction was allowed to stir at ambient temperature for 22 hours. The reaction mixture was concentrated and the residue was purified by preparative HPLC on a Waters Nova-Pak® HR C18 6 μm 60 {acute over (Å)} Prep-Pak® cartridge column (40 mm×100 mm) using a gradient of 10% to 100% acetonitrile in 10 mM aqueous ammonium acetate over 12 minutes at a flow rate of 70 mL/min to provide the title compound as a white solid (76.4 mg, 22%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.21-1.26 (m, 6H), 1.60-1.75 (m, 12H), 1.94-1.99 (m, 3H), 2.09-2.20 (m, 2H), 3.09-3.18 (m, 1H), 7.50-7.55 (m, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.82-7.88 (m, 1H), 8.12 (dd, J=7.9, 1.2 Hz, 1H), 10.80 (s, 1H) ppm; MS (DCI/NH3) m/z 380 (M+H)+; Elemental Analysis: Calculated for C23H29N3O2: C, 72.79; H, 7.70; N, 11.07. Found: C, 72.79; H, 7.81; N, 11.07.

Provenance & Evidence