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With hydrogen; In ethanol; at 20.0℃; under 2625.26 Torr;
800 mg of the compound described under INT11) is dissolved in 50 ml ethanol and mixed with 50 mg Raney nickel. It is hydrated in a 3.5 bar hydrogen atmosphere at ambient temperature. After filtration over kieselguhr and condensing off the solvent on the rotary evaporator, 610 mg of title compound is obtained. 1H-nMR (DMSO-d6): delta=1.09 (t, 3H); 3.11 (m, 2H); 5.48 (s, 2H); 5.52 (d, 1H); 5.71 (t, 1H); 5.78 (dd, 1H); 7.49 (d, 1H) ppm.
cyano-[3-ethyl-5-[1-(2-ethylamino-pyridin-4-ylamino)-meth-(Z)-ylidene]-4-oxo-thiazolidin-2-ylidene]-acetic acid allyl ester[ No CAS ]
cyano-[3-ethyl-5-[1-(2-ethylamino-pyridin-4-ylamino)-meth-(E)-ylidene]-4-oxo-thiazolidin-2-ylidene]-acetic acid allyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In propan-1-ol; for 4.0h;Heating / reflux;
0.94 g of the compound described under INT12) is dissolved in 50 ml 1-propanol. 1.85 g of the compound described under INTT5) is added and it is stirred for 4 hours under reflux. After cooling, the reaction mixture is filtered. After purification by chromatography on silica gel, the solid substance yields 1.48 g of title compound as pH-dependent 5-(E/Z)-isomer mixture. 1 H-nMR (DMSO-d6, stored over K2CO3, main isomer): delta=1.13 (t, 3H); 1.26 (t, 3H); 3.24 (pentuplet, 2H); 4.25 (q, 2H); 4.72 (d, 1H); 5.28 (d, 1H); 5.39 (d, 1H); 5.90-6.07 (m, 1H); 6.25 (d, 1H); 6.44 (dd, 1H); 6.49 (t, 1H); 7.85 (d, 1H); 8.13 (s, 1H); 10.47 (s, 1H) ppm.
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