2-[(2,6-Dichlorobenzyl)amino]-N-(4-methylthiazol-2-yl)acetamide

In the title compound, C13H13Cl2N3OS, the thiazole and benzene rings are roughly parallel to one another in two layers [dihedral angle = 5.08 (2)°] because the N—C—C—N—C chain that links the two rings is folded [N—C—C—N torsion angle = 12.0 (2)°] rather than fully extended. An intramolecular N—H⋯N interaction occurs. In the crystal, weak intermolecular N—H⋯N and C—H⋯O interactions are present and π–π interactions are indicated by the short distances [3.507 (3)–3.665 (2) Å] between the centroids of the thiazole and benzene rings.

In the title compound, C 13 H 13 Cl 2 N 3 OS, the thiazole and benzene rings are roughly parallel to one another in two layers [dihedral angle = 5.08 (2) ] because the N-C-C-N-C chain that links the two rings is folded [N-C-C-N torsion angle = 12.0 (2) ] rather than fully extended. An intramolecular N-HÁ Á ÁN interaction occurs. In the crystal, weak intermolecular N-HÁ Á ÁN and C-HÁ Á ÁO interactions are present andinteractions are indicated by the short distances [3.507 (3)-3.665 (2) Å ] between the centroids of the thiazole and benzene rings.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2286).  (Cheon et al., 2005;Kondo et al., 2007;Sakashita et al., 2006) and the title compound was prepared as a novel DPP-IV inhibitor (Zhan et al., 2009). We reported the crystal structure here.

Experimental
A round-bottomed flask was charged with [(2,6-dichlorophenyl)methyl]amine (1.76 g, 10 mmol), 2-[(2chloroacetyl)amino]-4-methylthiazole (1.91 g, 10 mmol), triethylamine (1.21 g, 12 mmol) and THF (20 ml), and the resulting mixture was stirred at room temperature over night. The reaction mixture was concentrated on a rotary evaporator and diluted with 100 ml of dichloromethane, and the organic solution thus obtained was washed with saturated brine, dried over sodium sulfate and evaporated on a rotary evaporator to afford a solid residue, which was triturated with a mixed solvent consisting of 5 ml of dichloromethane and 10 ml of ethyl acetate and filtered. The crystals were collected and dried to yield the title compound as colorless crystals 2.51 g (Yield 76.1%). Crystals suitable for single-crystal X-ray diffraction were obtained via slow evaporation at room temperature of a solution of the pure title compound in dichloromethane.

Refinement
All H atoms were found on difference maps. The H atoms of secondary amine were refined freely, giveing 0.84 or 0.89 Å, and C-H hyrdogens in the final cycles of refinement using a riding model, giveing 0.95-0.99 Å, with U iso (H) = 1.2U eq (C) and 1.5U eq (C) for the methyl H atoms.
supplementary materials sup-2 Figures   Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.