Pyridine → HCID 86270487, 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 room temperature was added pyridine (0.0200 mL, 0.247 mmol) followed by isopropyl carbonochloridate (18.2 mg, 0.148 mmol). The reaction mixture was stirred at ambient temperature for 12 h then 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 32 as described in general methods) to afford isopropyl (5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridin-3-yl)carbamate (35.0 mg, 57.7%). LCMS (Condition 4): retention time 2.16 min, [M+1]=491.0. HPLC (Condition 28): retention time=6.66 min, purity 95.13%. 1H NMR (400 MHz, DMSO-d6) δ 1.29 (d, J=6.0 Hz, 6 H), 4.65 (d, J=4.0 Hz, 2 H), 4.93 (sept, J=6.0 Hz, 1 H), 6.28 (t, J=4.0 Hz, 1 H), 7.22 (dd, J=6.0 Hz, J=7.6 Hz, 1 H), 7.28 (d, J=8.0 Hz, 1 H), 7.45-7.60 (m, 5 H), 7.68-7.73 (m, 2 H), 7.84-7.93 (m, 2 H), 8.17 (t, J=2.0 Hz, 1 H), 8.22-8.24 (m, 1 H), 8.48 (d, J=2.0 Hz, 1 H), 8.81 (d, J=2.0 Hz, 1 H), 10.00 (s, 1 H).

Provenance & Evidence