2-[4-(4-Methylphenylsulfonyl)piperazin-1-yl]-1-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)ethanone

Duan Niu; Shu-Yun Huang; Ping-Bao Wang; Deng-Ke Liu

doi:10.1107/S1600536811028716

. 2011 Jul 23;67(Pt 8):o2134. doi: 10.1107/S1600536811028716

2-[4-(4-Methylphenylsulfonyl)piperazin-1-yl]-1-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)ethanone

Duan Niu ^a, Shu-Yun Huang ^b, Ping-Bao Wang ^b, Deng-Ke Liu ^b,^*

PMCID: PMC3213574 PMID: 22091151

Abstract

In the title thienopyridine derivative, C₂₀H₂₅N₃O₃S₂, the piperazine ring exhibits a chair conformation and the tetrahydropyridine ring exhibits a half-chair conformation. The folded conformation of the molecule is defined by the N—C—C—N torsion angle of −70.20 (2) °. Intermolecular C—H⋯S and C—H⋯O hydrogen bonds help to establish the packing.

Related literature

For background to the bioactivity and applications of the title compound, see: Cattaneo (2009 ▶); Wallentin (2009 ▶). For a related structure, see: Zhi et al. (2011 ▶). For the synthesis of the title compound, see: Liu et al. (2008 ▶).

Experimental

Crystal data

C₂₀H₂₅N₃O₃S₂
M _r = 419.55
Orthorhombic,
a = 13.062 (2) Å
b = 15.710 (3) Å
c = 19.798 (3) Å
V = 4062.8 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.934, T _max = 0.950
49454 measured reflections
4844 independent reflections
4463 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.143
S = 1.14
4844 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 1.17 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028716/fl2350sup1.cif

e-67-o2134-sup1.cif^{(22.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028716/fl2350Isup2.hkl

e-67-o2134-Isup2.hkl^{(237.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811028716/fl2350Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811028716/fl2350Isup4.cml

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
C5—H5A⋯S1ⁱ	0.99	2.77	3.469 (2)	128
C6—H6A⋯O1ⁱⁱ	0.99	2.52	3.470 (3)	161
C6—H6B⋯O2ⁱⁱⁱ	0.99	2.51	3.346 (3)	143

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

Acknowledgments

The authors thank Mr Hai-Bin Song of Nankai University for the X-ray crystallographic determinations and helpful suggestions.

supplementary crystallographic information

Comment

As a thienopyridine derivative, the title compound(I) can be used as an irreversible P2Y12 antagonist to inhibit ADP, which induces platelet aggregation and decreases the risk of arterial occlusion. (Cattaneo 2009; Wallentin 2009).

The piperazine ring exhibits a chair conformation and the tetrahydropyridine ring exhibits a half chair conformation (Fig. 1). The folded conformation of the molecule is defined by the N1—C8—C9—N2 torsion angle of -70.20 (2) °. The dihedral angles formed between the tetrahydropyridine plane and the phenyl ring and the C10—C11—C12—C13 plane are 85.47 (6) ° and 56.38 (9) °, respectively. The crystal is stabilized by intermolecular C—H···S and C—H···O hydrogen bonds (Table1, Fig.2).

Experimental

2-Chloroacetyl chloride was added dropwise into a mixture of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine, dichloromethane and TEA at 263k-273k. After stirring for 3 h, the solvent was evaporated and a light yellow oily substance was obtained by silica gel column chromatography. The light yellow oily substance was then dissloved in a mixture of acetonitrile, TEA and 1-tosylpiperazine. After stirring for 5 h, the title compound was obtained by silica gel column chromatography. Crystallization of the resultingg white solid from methanol afforded white crystals suitble for X-ray analysis.