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

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Reaction Conditions

Reaction Steps

Cyclohexyl amine (0.3 ml, 2.7 mmol) was added to a solution of Example 133 (0.4 g, 0.9 mmol) in DMF (10 mL). The reaction mixture was stirred at 80° C. for 3 h, concentrated, treated with water and the solid that precipitated was filtered, washed with water and purified using flash chromatography (silica gel, 2% methanol/chloroform) to obtain the title compound. Yield: 0.365 g (80%); 1H NMR (CDCl3): δ 1.21 (q, 2H, CH2), 1.25 (q, 2H, CH2), 1.63 (bs, 2H, CH2), 1.73 (bs, 2H, CH2), 1.88 (bs, 2H, CH2), 2.44 (m, 1H, CH), 2.77 (s, 3H, CH3), 3.4 (s, 2H, CH2), 3.9 (s, 3H, OCH3), 4.7 (s, 2H, CH2), 7.57 (d, 1H, Ar), 7.83 (d, 1H, Ar), 8.1 (s, 1H, Ar), 8.4 (s, 1H, Ar), 9.72 (s, 1H, NH); MS m/e (ES+) 507 (M+1).

Provenance & Evidence