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0 °C

3-((8-chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (118) (200 mg, 0.64 mmol) and 4-methoxypiperidine (73.2 mg, 0.64 mmol) were added to DMF (5 mL), to this was added N-ethyl-N-isopropylpropan-2-amine (0.170 mL, 0.95 mmol) and then HBTU (362 mg, 0.95 mmol). The reaction mixture was stirred for four hours at 0° C. The crude mixture was purified by preparative LCMS (Waters XBridge Prep C18 OBD column, 5μ silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the desired material as a white crystalline solid (62.2 mg, 23.76% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.62-2.00 (3H, m), 3.02-3.29 (2H, m), 3.35 (3H, s), 3.37-3.65 (3H, m), 3.87-4.08 (1H, m), 4.69 (2H, s), 7.15-7.24 (3H, m), 7.29-7.34 (1H, m), 7.65 (1H, t), 7.77-7.81 (1H, m), 8.48 (1H, m), 9.85-10.01 (1H, m); m/z (LC-MS, ESI+), RT=1.80 (M+H 412.1).

1. customThe crude mixture was purified by preparative LCMS (Waters XBridge Prep C18 OBD column, 5μ silica, 30 mm diameter, 100 mm length)
2. additionFractions containing the desired compound
3. customwere evaporated to dryness