Sodium hydride → HCID 118184963, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (69 mg, 1.73 mmol, 3.00 equiv, 60% dispersion in mineral oil) was treated with trans-4-(dimethylamino)cyclohexan-1-ol (164 mg, 1.15 mmol, 2.00 equiv) in distilled DMF (15 mL) at room temperature for 1 h under nitrogen. Then a solution of 12-chloro-7-thiatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraene (120 mg, 0.57 mmol, 1.00 equiv) in 3 mL of DMF was added via syringe and the resulting solution was stirred for 2 h at 80° C. in an oil bath. After cooling, the reaction was quenched with water and extracted with 5×50 mL of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product (100 mg) was purified by preparative HPLC under the following conditions (Waters): Column: Xbridge Prep C18, 5 μm, 19*50 m; water with 0.05% NH4HCO3 and CH3CN (10% CH3CN up to 40% CH3CN in 10 min); flow rate: 20 mL/min; UV detection at 254 nm. The product-containing fractions were collected and partially evaporated to remove water and CH3CN under reduced pressure. The residue was lyophilized overnight to give the desired N,N-dimethyl-4-[7-thiatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexan-1-amine (56.9 mg) as a brown solid. MS (ES): m/z: 317 (M+H)+. 1H NMR (400 MHz, CDCl3): δ 1.49-1.64 (4H, m), 2.04 (2H, d), 2.29 (2H, d), 2.36 (6H, s), 2.43-2.51 (2H, m), 2.99-3.08 (4H, m), 4.37-4.45 (1H, m), 6.67 (1H, d, J=5.6 Hz), 8.27 (1H, d, J=5.6 Hz).

Provenance & Evidence