Hydrochloric Acid → HCID 67371415, Verbindung

Temperatur

60 °C

To a solution of 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(piperidin-4-yloxy)-pyridazine dihydrochloride (Example 14, 0.2 mmol, 97 mg) in EtOH (2 mL) was added 2-bromoethyl methyl ether (0.6 mmol, 57 μL), and potassium carbonate (0.6 mmol, 83 mg). The mixture was stirred at 60° C. for 3 hours, then cooled to room temperature, and filtered through celite. The celite cake was washed with DCM. The organic layers were combined and condensed in vacuo, and the residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH) to give a colorless sticky solid, which was dissolved in DCM (2 mL), 1N HCl in ether (2 mL) was added, kept at room temperature for 10 min, condensed, triturated with hexanes to provide the title compound (52 mg). LCMS: m/z 469 [M+1]. 1H NMR (400 MHz, CD3OD): δ 7.31-7.40 (3 H, m), 7.06-7.10 (2 H, m), 5.38-5.57 (1 H, m), 4.39-4.44 (1 H, m), 3.53-3.78 (4 H, m), 3.43 (3 H, s), 3.25-3.42 (4 H, m), 2.96-3.02 (2 H, m), 2.04-2.55 (4 H, m), 1.97-2.02 (2 H, m), 1.78-1.83 (2 H, m), 1.29-1.62 (8 H, m), 1.22-1.30 (2 H, m), 0.80 (3 H, t).

1. temperaturecooled to room temperature
2. filtrationfiltered through celite
3. washThe celite cake was washed with DCM
4. customcondensed in vacuo
5. customthe residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH)
6. customto give a colorless sticky solid, which
7. waitkept at room temperature for 10 min
8. customcondensed
9. customtriturated with hexanes

ORD-Eintrag

ord-8bfcdaae250b46d2b5721b856a054073

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09045461B2