p-Toluenesulfonic acid → HCID 24986498, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-benzyl-4-[(2,2-dimethoxyethyl)amino]-1-[4-fluoro-4′-(methylsulfonyl)biphenyl-2-yl]-7-methyl-1,3,8-triazaspiro[4.5]dec-3-en-2-one (50 mg, 0.08 mmol) in toluene (2.0 ml) was added p-toluenesulfonic acid (20 mg, 0.01 mmol). The reaction was sealed and allowed to stir at 110° C. The reaction was purified via reverse phase chromatography and neutralized with sodium bicarbonate. The product was extracted with EtOAc, dried over sodium sulfate, filtered, and concentrated in vacuo to yield the title compound as cis and trans mixture-1′-benzyl-6-[4-fluoro-4′-(methylsulfonyl)biphenyl-2-yl]-2′-methylspiro[imidazo[1,5-a]imidazole-7,4′-piperidin]-5(6H)-one. LCMS (M+H) 544.9. 1H NMR (400 MHz, CD3OD) δ 7.98 (m, 1H), 7.89 (m, 1H), 7.66 (m, 3H), 7.55 (m, 1H), 7.46 (m, 1H), 7.40 (dt, J=8.8, 2.8 Hz, 0.5H), 7.32 (dt, J=9.2, 2.8 Hz, 0.5H), 7.22 (m, 5H), 6.91 (m, 0.5H), 6.79 (m, 0.5H), 4.10 (m, 1H), 3.12 (s, 1.5H), 3.06 (s, 1.5H), 3.02 (s, 1H), 2.81 (m, 1H), 2.71-2.40 (m, 2H), 2.04-1.85 (m, 1H), 1.78-1.57 (m, 3H), 1.32 (s, 3H).

Provenance & Evidence