Benzylamine → 4-(5-Aminopyridin-3-yl)-N-benzyl-8-phenylphthalazin-1-amine

Participants

Reaction Steps

4-(5-Aminopyridin-3-yl)-N-benzyl-8-phenylphthalazin-1-amine (0.300 g, 30.9% yield, white solid) was prepared from 5-(4-chloro-5-phenylphthalazin-1-yl)pyridin-3-amine (0.800 g, 2.40 mmol) and benzylamine (10.0 mL, 92.0 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 combiflash (REDISEP®, silica gel, 12 g, 8% MeOH/CHCl3). The resulting residue was further purified by preparative HPLC (Condition 21 as described in general methods). LCMS (Condition 5): retention time 2.03 min, [M+1]=404.6. HPLC (Condition 28): retention time=5.47 min, purity 97.63%. 1H NMR (400 MHz, DMSO-d6) δ 4.49 (d, J=5.2 Hz, 2 H), 4.99 (t, J=5.2 Hz, 1 H), 5.52 (s, 2 H), 7.01-7.03 (m, 2 H), 7.15-7.28 (m, 4 H), 7.43-7.50 (m, 5 H), 7.66 (dd, J=2.0 Hz, J=6.4 Hz, 1 H), 7.85-7.90 (m, 2 H), 7.94 (d, J=2.0 Hz, 1 H), 8.09 (d, J=2.0 Hz, 1 H).

Provenance & Evidence