Hydrochloric Acid → HCID 131724539, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-cis-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline free base from EXAMPLE 11 (124 mg, 0.58 mmol) in 5 mL of 1,4-dioxane was added n-butylbromide (79 mg, 0.58 mmol), potassium carbonate (160 mg, 1.16 mmol) and potassium iodide (10 mg, 0.06 mmol) The mixture was stirred at 90° C. for 24 h. The reaction was then cooled, diluted with ethyl acetate, washed with brine, dried (Na2SO4) and concentrated. The residue was purified by preparative HPLC (C18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA) and the product containing fractions were concentrated, basified with sat'd aq Na2CO3 and extracted twice with ethyl acetate. The organics were washed with brine, dried (Na2SO4) and concentrated to a free base. The residue was taken up in about 4:1 ether/ethanol and then there was added 2M HCl in ether (1.0 mL, 2.0 mmol). The resulting solid was filtered, washed twice with ether and dried in vacuo to afford the title compound of EXAMPLE 104 as an off-white powder. 1H NMR (dmso-D6) δ: 6.90-6.78 (m, 2H), 6.62-6.55 (m, 1H), 4.00-3.93 (m, 1H), 3.85-3.77 (m, 1H), 3.65-3.59 (m, 1H), 3.50-3.35 (m, 2H), 3.15-2.95 (m, 4H), 2.92-2.75 (m, 3H), 2.73-2.63 (m, 2H), 1.95-1.85 (m, 2H), 1.65-1.55 (m, 2H), 1.33-1.22 (m, 2H), 0.91-0.83 (m, 3H). LRMS. (ES)+: 271.2 (M+H)+.

Provenance & Evidence