Triethylamine → HCID 10247806, compound

Participants

Reaction Conditions

Reaction Steps

To 500 mg (1.24 mmol) of 1-8 in 15 mL of THF was added 260 μL (1.87 mmol) of triethylamine, the solution was cooled to 0° C., and 129 mg (0.44 mmol) of triphosgene was added. The highly viscous solution was stirred for 30 min, 203 mg (2.5 mmol) of dimethylamine hydrochloride and an additional 870 μL (6.22 mmol) of triethylamine were added, the reaction was warmed to room temperature and stirring was continued for 5 h. The mixture was dumped into a separatory funnel containing 10% aqueous KHSO4 and EtOAc, the layers were separated, the organic phase was washed with brine, dried over Na2SO4, and concentrated to provide a pale yellow oil. This was then dissolved in 10 mL of dry CH3CN, 600 μL (3.7 mmol) of triethylamine trihydrofluoride was added, and the reaction was allowed to stir at room temperature overnight. The reaction was quenched with saturated NaHCO3, extracted twice with EtOAc, washed with brine, dried over Na2SO4, concentrated, and the residue purified by silica gel chromatography with EtOAc/hexanes to provide 1-9 as a white solid. Data for 1-9: 1HNMR (500 MHz, CDCl3) δ 7.4-7.2 (m, 5H), 7.1-6.9 (m, 3H), 6.3 (s, 1H), 5.5 (m, 1H), 4.85 (m, 1H), 4.65 (d, 1H), 4.4 (m, 1H), 4.0 (d, 1H), 3.0 (s, 6H) ppm. HRMS (ES) calc'd M+H for C20H20F2N2O2: 359.1566. Found: 359.1567.

Provenance & Evidence