Pyridine → HCID 86270486, compound

Participants

Reaction Steps

To a solution of 4-(5-aminopyridin-3-yl)-8-phenyl-N-(pyridin-2-ylmethyl) phthalazin-1-amine (50.0 mg, 0.124 mmol) in dichloromethane (5 mL) at ambient temperature was added pyridine (0.0200 mL, 0.247 mmol) followed by acetyl chloride (0.0132 mL, 0.185 mmol). After stirring for 5 h at room temperature, the reaction mixture was diluted with dichloromethane (50 mL) and the organic portion washed with water (10 mL) followed by brine (10 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by preparative HPLC (Condition 31 as described in general methods) to obtain N-(5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridin-3-yl)acetamide (25.0 mg, 45.3%) as a white solid. LCMS (Condition 4): retention time 2.08 min, [M+1]=447.2. HPLC (Condition 28): retention time=5.63 min, purity 94.65%. 1H NMR (400 MHz, CD3OD) δ 2.21 (s, 3 H), 4.65 (s, 2 H), 7.21-7.26 (m, 2 H), 7.49 (br s, 5 H), 7.69-7.73 (m, 2 H), 7.88-7.94 (m, 2 H), 8.28-8.30 (m, 1 H), 8.42 (dd, J=2.0 Hz, J=2.4 Hz, 1 H), 8.55 (d, J=2.0 Hz, 1 H), 8.90 (d, J=2.4 Hz, 1 H).

Provenance & Evidence