(IUCr) Crystallography Journals Online

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Acta Cryst. (2008). E64, o701 [ doi:10.1107/S160053680800487X ]

6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

F. Lehmann, D. Schollmeyer and S. Laufer

Abstract: The crystal structure of the title compound, C₂₅H₁₈ClN₅O, was determined in the course of our studies on the synthesis of 1,4-dihydropyrano[2,3-c]pyrazole as an inhibitor of the p38 mitogen-activated protein kinase (MAPK). The compound was prepared via a base-catalysed synthesis from 1-benzyl-3-(4-pyridyl)-1H-pyrazol-5(4H)-one with p-chloroaldehyde and malononitrile. The crystal data obtained were used to generate a three-dimensional pharmacophore model for in silico database screening. The phenyl ring is disordered over two positions, with site occupancy factors of 0.55 and 0.45. The dihedral angles between the 1,4-dihydropyrano[2,3-c]pyrazole unit and the chlorophenyl and pyridine rings are 83.7 (1) and 16.0 (1)°, respectively. The chlorophenyl and pyridine rings make a dihedral angle of 86.8 (2)°.

Online 12 March 2008