Phenylsuccinic Anhydride → N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-phenylsuccinamic acid

Participants

Reaction Steps

A stirred mixture of 4-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one (0.7 g, 2.6 mmol; prepared in a manner similar to that described in Example 23), 3-phenyldihydrofuran-2,5-dione (0.458 g, 2.6 mmol) and toluene (35 ml) was heated under reflux for 2 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with ethyl acetate (3 ml) and dried in vacuo to give N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-phenylsuccinamic acid (0.775 g) as an off-white solid, m.pt. 180–183° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 2.7–2.9 (m, 1H) (—CHHCHPh—), 3.1–3.3 (m, 1H) (—CHHCHPh—), 4.0–4.1 (m, 1H) (—CHPh—) 4.3 (s, 2H) (ArCH2—), 7.1–7.3 (m, 2H) (2×ArH), 7.3–7.5 (m, 5H) (5×ArH), 7.8–8.0 (m, 4H) (4×ArH), 8.3 (d, 1H) (ArH), 9.75 (s, 1H) (chain CONH), 12.5 (br s, 1H) (—CO2H), 12.65 (s, 1H) (ring CONH) ; m/z (M+H)+. 446, 100% purity.

Provenance & Evidence