2-Pyridinemethanamine → N-(tert-butyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide (0.400 g, 0.883 mmol) in toluene (5 mL) was added pyridin-2-ylmethanamine (0.0950 g, 0.883 mmol) and the contents were heated at 100° C. for 12 h. The volatile components were removed under reduced pressure and the resulting residue was purified by preparative HPLC (Condition 16 as described in general methods) to yield N-(tert-butyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamide (35.0 mg, 7.55%) as a white solid. LCMS (Condition 4): retention time 2.47 min, [M+1]=525.2. HPLC (Condition 28): retention time=6.97 min, purity 96.32%. 1H NMR (400 MHz, CD3OD) δ 1.30 (s, 9 H), 4.68 (s, 2 H), 7.24 (dd, J=4.8 Hz, J=7.2 Hz, 1 H), 7.27 (d, J=7.6 Hz, 1 H), 7.52 (br s, 5 H), 7.72 (dd, J=1.6 Hz, J=7.6 Hz, 1 H), 7.77 (dd, J=1.2 Hz, J=7.2 Hz, 1 H), 7.84 (dd, J=1.2 Hz, J=8.4 Hz, 1 H), 7.91-7.96 (m, 1 H), 8.31 (d, J=4.4 Hz, 1 H), 8.55 (t, J=2.0 Hz, 1 H), 9.07 (d, J=2.0 Hz, 1 H), 9.18 (d, J=2.0 Hz, 1 H).

Provenance & Evidence