2-(2-bromoethyl)-1,3-dioxane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(piperidin-4-yloxy)-pyridazine dihydrochloride (Example 14, 0.1 mmol, 49 mg) in DMF (1 mL) was added 2-(2-bromoethyl)-1,3-dioxane (0.3 mmol, 40 μL), and potassium carbonate (0.4 mmol, 56 mg). The mixture was stirred at room temperature for 3 hours. It was then diluted with water/EtOAc. The organic layers were combined, dried, and condensed in vacuo and the residue was purified by silica gel chromatography (DCM to DCM+10% 2N ammonia in MeOH) to give a colorless sticky solid, which was dissolved in DCM (1 mL), 1N HCl in ether (1 mL) was added, kept at room temperature for 10 min, condensed, triturated with hexanes to provide the title compound (22 mg). LCMS: m/z 525 [M+1]. 1H NMR (400 MHz, CD3OD): δ 7.72 and 7.81 (1H, s), 7.44-7.49 (2H, m), 7.12-7.17 (2H, m), 5.38-5.57 (1H, m), 4.76-4.79 (1H, m), 4.41-4.48 (1H, m), 4.06-4.13 (2H, m), 3.72-3.86 (3H, m), 3.55-3.60 (1H, m), 3.22-3.39 (4H, m), 3.12-3.17 (2H, m), 2.23-2.57 (3H, m), 1.98-2.17 (6H, m), 1.79-1.86 (2H, m), 1.23-1.64 (11H, m), 0.82 (3H, t). dried condensed in vacuo the residue was purified by silica gel chromatography (DCM to DCM+10% 2N ammonia in MeOH) to give a colorless sticky solid, which kept at room temperature for 10 min condensed triturated with hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure described in Ex. 8, 4-(4-methoxystyryl)pyridine and 2-(2-bromoethyl) 1,3-dioxane were reacted to obtain N-[2-(1,3-dioxane-2-yl)ethyl]-4-(4-methoxystyryl)pyridinium bromide.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure described in Ex. 8, 4-(4-methylstyryl)pyridine and 2-(2-bromoethyl) 1,3-dioxane were reacted to obtain N-[2-(1,3 dioxane-2-yl)ethyl]-4-(4-methylstyryl)pyridinium bromide.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-styrylpyridine (1.81 g) and 2-(2-bromoethyl) 1,3-dioxane (1.95 g) were stirred and refluxed in ethylacetate (15 ml) solution for 15 hours. After cooling of the reaction mixture creamy crystals were separated by filtration, washed with ethyl ether and dried to give 3.4 g of N-[2-(1,3-dioxane-2-yl)ethyl]-4-styrylpyridinium bromide. After cooling of the reaction mixture creamy crystals were separated by filtration washed with ethyl ether dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(4-methylstyryl)quinoline (0.245 g) and 2-(2-bromoethyl) 1,3-dioxane (0.195 g) were mixed and refluxed in ethylacetate (1.5 ml) for 18 hours. Yellow-green precipitate was separated by filtration, washed with ethyl ether and dried in vacuo to give 0.308 g of N-[2-(1,3-dioxane-2-yl)ethyl]-4-(4-methylstyryl)-quinolinium bromide. Yellow-green precipitate was separated by filtration washed with ethyl ether dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir: