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Process for the preparation of crystalline forms of (E)-4-(4-(4-(2-cyanovinyl)-2,6-dimethylphenylamino)pyrimidin-2-ylamino)benzonitrile

IP.com Disclosure Number: IPCOM000205878D
Publication Date: 2011-Apr-06
Document File: 2 page(s) / 44K

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Process for the preparation of crystalline forms of (E)-4-(4-(4-(2-cyanovinyl)-2,6- dimethylphenylamino)pyrimidin-2-ylamino)benzonitrile

(E)-4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2- yl]amino}benzonitrile, which is a new drug, developed by Tibotec, for the treatment of HIV infection.

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Provided here is a crystallization procedure of (E)-4-{[4-({4-[(E)-2-cyanovinyl]-2,6- dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile.

(E)-3-(4-amino-3,5-dimethylphenyl)acrylonitrile hydrochloride (0.50 g, 2.4 mmol,) and 4-(4-chloropyrimidin-2-ylamino)benzonitrile (0.67 g, 2.51 mmol, 1.05 eq) were mixed in acetonitrile (10 mL, 20V) and heated to reflux. Stirring was continued at the same temperature for 69 h after which time the reaction mixture was cooled to 55°C and filtered. The filter cake was washed with acetonitrile (1 mL, 2V) and then dried in a vacuum oven at 50°C for 22 h. The resulting crude solid was mixed with a 10% aqueous solution of potassium carbonate (5.4 mL), stirred at room temperature for 0.5 h and then filtered. The filter cake was washed with water (2x2 mL) and dried at 50°C in a vacuum oven for 22 h. the resulting solid was mixed with isopropyl alcohol at reflux for 21 h and then the mixture was cooled to room temperature, filtered and the filter cake was dried in a vacuum oven at 50°C for 22 h to give the title compound as a mixture of polymorphs.


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