2-(2-(4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo- 2-thioxoimidazolidin-l-yl)butanamido)ethoxy)ethyl 2-(adamantan-l-yl)acetate

   Example 5; 2-(2-(4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo- 2-thioxoimidazolidin-l-yl)butanamido)ethoxy)ethyl 2-(adamantan-l-yl)acetate



To a 1 dram vial with stirbar was charged 4-(3-(4-cyano-3-
(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-l-yl)butanoic acid (10.0 mg, 0.025 mmol), EDC (7.0 mg, 0.038 mmol), HOBt (6.0 mg, 0.375 mmol), and 0.35 mL dichloromethane. After 15 minutes of stirring 2-(2-aminoethoxy)ethyl 2-(adamantan-l-yl)acetate (8.0 mg, 0.027 mmol) was added and the mixture left stir for 16 h upon which the mixture was diluted with 1 mL dichloromethane and washed with 10% aq. citric acid (2 X 1 mL), and saturated a₂C03 (2 X 1 mL). The organic layer was dried with Na₂S0₄ and concentrated down to yield a crude oil which was purified by silica gel chromatography (dichloromethane to 19: 1 dichloromethane: MeOH) to yield 5 mg (30% yield) of pure product as an amber oil.

H NMR (500 MHz, CDC1₃) δ 7.93 (d, J= 8.3, 1H), 7.87 (d, J= 1.7, 1H), 7.75 (dd, J= 1.9, 8.3, 1H), 6.04 (t, J= 5.1, 1H), 4.25 - 4.14 (m, 2H), 3.79 - 3.71 (m, 2H), 3.68 - 3.61 (m, 2H), 3.55 (t, J = 5.0, 2H), 3.49 - 3.40 (m, 2H), 2.32 (t, J = 6.7, 2H), 2.14 (dt, J = 6.8, 14.4, 2H), 2.08 (s, 2H), 1.95 (s, 4H), 1.70-1.66 (m, 4H), 1.65-1.55 (m, 13 H);  


¹³C NMR (126 MHz, CDCI₃) δ 178.6, 175.5, 172.0, 171.8, 137.3, 135.3, 133.6 (q, J = 33.4), 132.3, 127.2 (q, J= 4.7), 121.0 (q, J = 274.0), 115.0, 110.1 (q, J= 2.2), 69.7 69.3, 65.4, 62.7, 49.0, 43.7, 42.5, 39.4, 36.8, 33.0, 33.0, 28.7, 23.7, 23.2;


LRMS (ESI) 662.4 (M+H)⁺.

http://www.google.com/patents/WO2013170147A1?cl=en






DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE

Join me on Linkedin

Join me on Facebook FACEBOOK

Join me on twitter     

Join me on google plus Googleplus

 amcrasto@gmail.com