Yield:-

Reaction Conditions:

with triethylamine in tetrahydrofuran at 75; for 24 h;

Steps:

2 2-(amantadine-ylcarbamoyl)benzoic acid

Amantadine (500 mg, 3.31 mmol) and triethylamine (684 mg, 5.30 mmol) were added to a solution of phthalic anhydride (490.2 mg, 3.31 mmol) in THF (12 mL). The resulting mixture was heated at 75 ^oC for one day. The solvent was evaporated, and the crude product was purified with prep-HPLC to yield the title compound. (0207) [0169] ¹H NMR (500MHz, DMSO-d6): d 7.74- 7.72 (m, 1H), 7.54- 7.43 (m, 2H), 7.34- 7.32 (m, 1H), 2.03 (s, 9H), 1.64 (s, 6H), 1.73- 1.66 (m, 6H). (0208) [0170] LC/MS m/z calculated for [M+H]⁺ 300.2, found 300.2.

References:

WO2020/6262,2020,A1 Location in patent:Paragraph 0168-0170