N-(2-Chloropyrimidin-4-yl)-N,2-dimethyl-2H-indazol-6-amine

Abstract

In the title compound, C13H12ClN5, which is a derivative of the anti­tumor agent pazopanib {systematic name: 5-[[4-[(2,3-di­methyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl]amino]-2-methylbenzolsulfonamide}, the indazole and pyrim­idine fragments form a dihedral angle of 62.63 (5)°. In the crystal, pairs of mol­ecules related by twofold rotational symmetry are linked into dimers through π–π inter­actions between the indazole ring systems [centroid–centroid distance = 3.720 (2) Å]. Weak inter­molecular C—H⋯N hydrogen bonds further assemble these dimers into columns propagated in [001].

2-Methyl-6-nitro-2H-indazole

“…E67, o1546 In (I) ( Fig. 1), the bond lengths and angles are normal and comparable with those reported for related compounds (Qi et al, 2010;Chen et al, 2009). Rings N2/N3/C7/C6/C1 and C1-C6 are almost coplanar forming a dihedral angle 1.08 7°.…”

“…For the synthesis, see: Sorbera et al (2006); Balardi et al (1997). For related structures, see: Qi et al (2010); Chen et al (2009). For applications of indazole derivatives, see, for example: Li et al (2008).…”