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

Participants

Reaction Steps

A mixture of the product of Example 1B (45.4 mg, 0.223 mmol), pyridine (0.023 mL, 0.28 mmol), and (adamantan-1-yl)acetyl chloride (0.052 g, 0.24 mmol) in CH2Cl2 (0.8 mL) was stirred for 2 hours, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (eluted with 8% EtOAc/CH2Cl2) to give the title compound (0.0743 g, 0.196 mmol) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 11.09 (s, 1H), 8.35 (dd, 1H), 8.10 (d, 1H), 7.98 (td, 1H), 7.89 (ddd, 1H), 3.62 (quin, 1H), 2.03 (s, 2H), 1.95 (s, 3H), 1.76-1.52 (m, 12H), 1.26 (d, 6H); MS (ESI−) M/Z 378.1 (M−H)−.

Provenance & Evidence