4-Methoxypiperidine → 5-Chloro-4-(3-(4-methoxypiperidine-1-carbonyl)benzyl)phthalazin-1(2h)-one

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence