2-Pyridinemethanamine → Ethyl 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinate

Participants

Reaction Steps

Ethyl 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinate (3.10 g, 88.0%, brown solid) was prepared from 5-(4-chloro-5-phenylphthalazin-1-yl)nicotinate (3.00 g, 7.70 mmol) and 2-(aminomethyl)pyridine (10.0 mL, 97.0 mmol) by the methods described for the preparation of N-(tert-butyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamide in Example 1. The residue was purified by preparative HPLC (Condition 15 as described in general methods). LCMS (Condition 2): retention time 1.90 min, [M+1]=462.2. HPLC (Condition 25): retention time=7.06 min, purity 96.07%. 1H NMR (400 MHz, DMSO-d6) δ 1.38 (t, J=7.2 Hz, 3 H), 4.42 (q, J=7.2 Hz, 2 H), 4.67 (d, J=4.4 Hz, 2 H), 6.35 (dd, J=4.0 Hz, J=4.4 Hz, 1 H), 7.21-7.25 (m, 1 H), 7.28 (d, J=8.0 Hz, 1 H), 7.50-7.61 (m, 5 H), 7.69-7.73 (m, 2 H), 7.84 (dd, J=1.6 Hz, J=8.4 Hz, 1 H), 7.93 (dd, J=7.2 Hz, J=8.4 Hz, 1 H), 8.23 (dt, J=0.8 Hz, J=4.8 Hz, 1 H), 8.53 (t, J=2.0 Hz, 1 H), 9.11 (d, J=2.0 Hz, 1 H), 9.24 (d, J=2.0 Hz, 1 H).

Provenance & Evidence