5-(2-Chloro­benz­yl)-4,5,6,7-tetra­hydro­thieno[3,2-c]pyridin-2-yl acetate

Jing Yang; Na Chen; Hao Sun; Xiao-Xia Cao; Deng-Ke Liu

doi:10.1107/S1600536812010045

. 2012 Mar 14;68(Pt 4):o1053. doi: 10.1107/S1600536812010045

5-(2-Chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate

Jing Yang ^a,^*, Na Chen ^a, Hao Sun ^a, Xiao-Xia Cao ^a, Deng-Ke Liu ^b

PMCID: PMC3344014 PMID: 22589923

Abstract

In the title compound, C₁₆H₁₆ClNO₂S, the benzene and thiophene rings make a dihedral angle of 72.60 (4)°. In the crystal, weak C—H⋯O interactions are observed.

Related literature

The title compound is a derivative of the antiplatelet agent clopidogrel [systematic name (+)-(S)-methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate]. For background to the bioactivity and applications of clopidogrel, see: Muller et al. (2003 ▶); Savi et al. (1994 ▶); Sharis et al. (1998 ▶). For the synthesis of the title compound, see: Roquettes et al. (1993 ▶).

Experimental

Crystal data

C₁₆H₁₆ClNO₂S
M _r = 321.81
Monoclinic,
a = 14.526 (3) Å
b = 6.1065 (12) Å
c = 17.490 (3) Å
β = 99.098 (3)°
V = 1532.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.926, T _max = 0.962
10686 measured reflections
2704 independent reflections
2397 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.086
S = 1.07
2704 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.31 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) I, global. DOI: 10.1107/S1600536812010045/kp2393sup1.cif

e-68-o1053-sup1.cif^{(19KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010045/kp2393Isup2.hkl

e-68-o1053-Isup2.hkl^{(132.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010045/kp2393Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812010045/kp2393Isup4.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
C15—H15⋯O1ⁱ	0.95	2.52	3.364 (2)	148

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Clopidogrel is an oral, thienopyridine class of antiplatelet agent used to inhibit blood clots in coronary artery disease, peripheral vascular disease, and cerebrovascular disease (Muller et al., 2003; Savi et al., 1994; Sharis et al., 1998). The molecular structure of the title compound, a derivative of clopidogrel, is reported here. The thiophene and benzene rings make a dihedral angle of 72.60 (4)°; the tetrahydropyridine ring adopts a half-chair conformation (Fig. 1). In the crystal structure, the packing is realsied by weak intramolecular C—H···Cl and C—H···N, and intermolecular C—H···O interaction (Table 1).

Experimental

We used the method of Roquettes et al. (1993) to sythesize the title compound. 8.85 g (0.0316 mol) of 5-(2-chlorobenzyl)-5,6,7,7a-tetrahydro-4H-thieno [3,2-c] pyridine-2-one are dissolved in 120 mL of isopropenyl acetate with 7.8 g (0.0411 mol) of p-toluenesulphonic acid; the medium is stirred at 363 K for 6 h. After cooling to about 293 K, 2 volumes of water are introduced into the medium, the pH is made basic by adding saturated aqueous NaHCO₃ solution and the desired product is extracted with ethyl acetate. After removal of the solvent, the oil, dissolved in CH₂Cl₂, is filtered on silica to give a 68% yield of the target compound. Colourless single crystals were grown from a methanol solution.