rac-tert-Butyl 2-{5-[(4-{2-[methyl(pyri­din-2-yl)amino]ethoxy}phenyl)methyl]-2,4-dioxo-1,3-thiazolidin-3-yl}acetate

Sixing Hu; Guojuan Liang; Dashu Fang; Yongjun Gan; Xiangnan Hu

doi:10.1107/S1600536811012177

. 2011 Apr 7;67(Pt 5):o1075. doi: 10.1107/S1600536811012177

rac-tert-Butyl 2-{5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-2,4-dioxo-1,3-thiazolidin-3-yl}acetate

Sixing Hu ^a, Guojuan Liang ^a, Dashu Fang ^a, Yongjun Gan ^a, Xiangnan Hu ^a,^*

PMCID: PMC3089241 PMID: 21754398

Abstract

The title compound, C₂₄H₂₉N₃O₅S, is a chiral molecule which crystallizes in a centrosymmetric space group as a racemate. The thiazolidine ring forms the dihedral angles of 29.22 (12) and 67.79 (10)° with the benzene and pyridine rings, respectively. The benzene and pyridine rings are tilted by dihedral angle of 67.18 (9)°. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a two-dimensional network.

Related literature

For the related structure of 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione, see: Lei et al. (2003 ▶); Balint & Nagy (2006 ▶).

Experimental

Crystal data

C₂₄H₂₉N₃O₅S
M _r = 471.56
Monoclinic,
a = 25.621 (5) Å
b = 9.886 (2) Å
c = 9.874 (2) Å
β = 97.32 (3)°
V = 2480.6 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 291 K
0.40 × 0.13 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.936, T _max = 0.980
23230 measured reflections
5574 independent reflections
2632 reflections with I > 2σ(I)
R _int = 0.084

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.162
S = 1.01
5574 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: RAPID-AUTO (Rigaku 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012177/kp2314sup1.cif

e-67-o1075-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012177/kp2314Isup2.hkl

e-67-o1075-Isup2.hkl^{(272.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6C⋯O1ⁱ	0.96	2.59	3.501 (3)	159
C19—H19B⋯O2ⁱⁱ	0.97	2.59	3.302 (4)	130

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by Natural Science Foundation of Chongqing. We also thank Chongqing Medical University for partial financial support of this work.

supplementary crystallographic information

Comment

The title compound is a type of thiazolidinedione material, which was synthesised from rosiglitazone and tert-butyl chloroacetate. In this paper, we report the synthesis and crystal structure of the title compound.

The title compound is chiral with a stereogenic centre C16 of the thiazolidine ring. However, it crystallises in the centrosymmetric space group as a racemate. The thiazolidine ring forms the dihedral angles of 29.22 (12) ° and 67.79 (10) ° with the benzene ring and pyridine ring, respectively. The benzene ring and the pyridine ring are tilted by 67.18 (9) ° (Fig. 1). In the crystal, intermolecular C—H···O hydrogen bonds link the molecules into a two-dimensional network (Table 1 and Fig. 2).

Experimental

A solution of C₂H₅ONa (1.00 g) in anhydrous ethanol (50 mL) was added slowly to a solution of rosiglitazone (5 g) in anhydrous ethanol (125 mL) at room temperature and the mixture was stirred for 12 h. After completion of the reaction, the mixture was filtered and the white powder was dried at 323 K to afford sodium rosiglitazone (5.15 g). tert-Butyl chloroacetate (0.80 g) was added to a suspension of sodium rosiglitazone (1.51 g) in acetonitrile (70 mL) and the mixture was refluxed for 11 h. After completion of the reaction, the warm suspension was filtered and the filtrates were concentrated under vacuum. Single crystals were obtained by recrystallisation from EtOH : EtOAc (1 : 2) at room temperature.