Glutaric anhydride → 4-[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]butyric acid

Participants

Reaction Steps

A stirred mixture of 4-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one (0.1 g, 0.37 mmol; prepared in a manner similar to that described in Example 23), glutaric anhydride (0.042 g, 0.37 mmol) and toluene (10 ml) was heated under reflux until the starting materials were consumed (the reaction was followed by tic using a 3:1 mixture of ethyl acetate and ethanol as eluant), then it was allowed to cool to ambient temperature. The resulting solid was collected by filtration and recrystallised from ethanol to give 4-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]butyric acid (0.08 g) as a white solid, mpt. 190–194° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 1.5–1.65 (m, 2H) (—CH2CH2CH2—), 2.0–2.25 (m, 4H) (—CH2CH2CH2—) 4.1 (s, 2H) (ArCH2—), 6.8–7.0 (m, 2H) (2×ArH), 7.5–7.8 (m, 4H) (4×ArH), 8.05 (d, 1H) (ArH), 9.45 (s, 1H) (chain CONH), 12.85 (br s, 1H) (—CO2H), 12.4 (s, 1H) (ring CONH); m/z (M−H)+. 382, 100% purity.

Provenance & Evidence