Trimethylsilyl isocyanate → HCID 86690654, compound

Participants

Reaction Steps

To a solution of N-[[2-fluoro-4-(4-piperidyl)phenyl]methyl]-1-phenyl-N-(2,2,2-trifluoroethyl)methanesulfonamide hydrochloride (Example 7, Step 2), (200 mg, 0.41 mmol) and N,N-diisopropylethylamine (0.36 mL, 2.0 mmol) in dichloromethane (4 mL) was added 4-dimethylaminopyridine (5 mg, 0.041 mmol), followed by isocyanato(trimethyl)silane (0.30 mL, 2.1 mmol) and the reaction was stirred at ambient temperature for 2 hours. Saturated aqueous NaHCO3 was then added and the dichloromethane layer was isolated with a phase-separator cartridge. The organic layer was concentrated and purified by preparative reverse phase HPLC to yield 27 mg of 4-(3-fluoro-4-((1-phenyl-N-(2,2,2-trifluoroethyl)methylsulfonamido)methyl)phenyl)piperidine-1-carboxamide. 1H NMR (400 MHz, DMSO) δ 7.44-7.38 (m, 5H), 7.38-7.29 (m, 1H), 7.16-7.02 (m, 2H), 5.88 (s, 2H), 4.59 (s, 2H), 4.41 (s, 2H), 4.13-4.00 (m, 2H), 3.95 (q, J=9.3 Hz, 2H), 2.82-2.61 (m, 3H), 1.80-1.64 (m, 2H), 1.56-1.32 (m, 2H); LCMS (m/z) ES+ 488.1 [M+1]+.

Provenance & Evidence