Trifluoroacetic acid → 2-[4-(3,6-Dioxo-8-phenyl-2,6-dihydro-3H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-2-methyl-propionitrile

Participants

Reaction Steps

To a stirred solution of 2-{4-[3,6-dioxo-8-phenyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,6-dihydro-3H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalen-7-yl]-phenyl}-2-methyl-propionitrile (55 mg, 0.1 mmol) in DCM (2 mL), cooled in an ice bath, was added TFA (1.5 mL) at RT. After 16 h, the reaction mixture was evaporated to dryness, the resultant residue was dissolved in THF (3 mL) and benzyltrimethylammonium hydroxide solution (0.06 mL, 40% in MeOH) was added. The reaction mixture was stirred at RT for 1.5 h. EtOAc and water were added and the mixture was acidified by the addition of 1 M HCl (1 mL). The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, EtOAc) to afford the title compound (20 mg, 47%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 10.05 (s, 1H), 7.72 (d, J=7.3 Hz, 1H), 7.46-7.38 (m, 5H), 7.33-7.22 (m, 5H), 1.73 (s, 6H). LCMS (Method E): RT=4.22 min, [M+H]+=423.

Provenance & Evidence