Crystal structure of 3-methyl-1-phenyl-6-propylamino-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

Abstract

In the title compound, C17H17N5, the dihedral angle between the 1H-pyrazolo[3,4-b]pyridine ring system (r.m.s. deviation = 0.001 Å) and the attached phenyl group is 2.56 (6)°. The propylamino side chain has a contorted conformation [Car—N—C—C = −77.97 (16)° and N—C—C—C = −57.37 (17)°]. An intramolecular C—H...N interaction closes an S(6) ring. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generate R22(12) loops. Aromatic π–π stacking interactions [centroid–centroid distance = 3.5726 (8) Å] are also observed.

Keywords

• crystal structure
• pyrazolo[3,4-b]pyridine
• amination
• nucleophilic substitution