Water → 4-Chloro-6-methyl-2-[2-(2-morpholin-4-yl-ethylamino)-ethylamino]-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

2-Morpholin-4-yl-ethylamine (0.18 mL, 1.44 mmol) and tetrabutylammonium iodide (0.075 g, 0.2 mmol) were sequentially added with stirring to a solution of the carboxylic acid of Example 56k (0.5 g, 1.2 mmol) in dry DMF (1 mL). The reaction mixture was then stirred at 120° C. for 3 h in an atmosphere of nitrogen. It was treated with cold water and the solid that precipitated was filtered, washed with water, and dried. The solid was treated with a methanolic HCl solution (10 mL), and refluxed at 70° C. for 3 h. The reaction mixture was concentrated and treated with an aqueous sodium bicarbonate solution. The solid that precipitated was filtered, washed with water, dried and purified using flash chromatography (silica gel, 2% methanol/chloroform) to obtain the title compound. Yield: 0.150 g, (24.19%); 1H NMR (DMSO-d6): δ 2.40 (t, 4H, 2CH2), 2.50-2.60 (m, 4H, 2CH2), 3.10 (m, 4H, 2CH2), 3.15-3.20 (m, 4H, 2CH2), 3.90 (s, 3H, OCH3), 4.50 (t, 1H, NH), 5.15 (s, 2H, CH2), 6.10 (t, 1H, NH), 6.7 (s, 2H, 2Ar), 8.10 (s, 1H, Ar), 8.25 (s, 1H, Ar); MS : m/e (EI+) 524 (M+).

Provenance & Evidence