Ammonia → 5-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinamide

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinate (230 mg, 0.288 mmol) in MeOH (5 mL) was purged with ammonia gas for 5 minutes at −10° C. The reaction mixture was heated in a sealed tube at 70° C. for 12 h. The volatile components were removed under reduced pressure and the resulting residue was purified by HPLC (Condition 20 as described in general methods) to afford 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinamide (50.0 mg, 39.8%) as a yellow solid. LCMS (Condition 2): retention time 1.90 min, [M+1]=433.0. HPLC (Condition 25): retention time=5.20 min, purity 98.63%. 1H NMR (400 MHz, DMSO-d6) δ 4.66 (d, J=4.0 Hz, 2 H), 6.32 (dd, J=4.0 Hz, J=4.4 Hz, 1 H), 7.22-7.24 (m, 1 H), 7.28 (d, J=7.6 Hz, 1 H), 7.51-7.60 (m, 5 H), 7.68-7.73 (m, 3 H), 7.84 (dd, J=1.2 Hz, J=8.4 Hz, 1 H), 7.93 (dd, J=7.2 Hz, J=8.4 Hz, 1 H), 8.22-8.24 (m, 1 H), 8.28 (br s, 1 H), 8.51 (t, J=2.0 Hz, 1 H), 8.99 (d, J=2.0 Hz, 1H), 9.18 (d, J=2.0 Hz, 1 H).

Provenance & Evidence