1-[(6-Chloro-3-pyrid­yl)meth­yl]-N-(4-ethoxy­phen­yl)-3-phenyl-1H-pyrazole-5-carboxamide

Zheng Tang; Xiao-Liang Ding; Wen-Liang Dong; Bao-Xiang Zhao

doi:10.1107/S1600536809010290

. 2009 Mar 25;65(Pt 4):o865–o866. doi: 10.1107/S1600536809010290

1-[(6-Chloro-3-pyridyl)methyl]-N-(4-ethoxyphenyl)-3-phenyl-1H-pyrazole-5-carboxamide

Zheng Tang ^a, Xiao-Liang Ding ^b, Wen-Liang Dong ^c, Bao-Xiang Zhao ^d,^*

PMCID: PMC2968942 PMID: 21582579

Abstract

In the title compound, C₂₄H₂₁ClN₄O₂, the pyrazole ring makes dihedral angles of 7.70 (11), 89.17 (11) and 40.68 (11)° with the phenyl, pyridine and ethoxyphenyl rings, respectively. There are some intramolecular C—H⋯O and C—H⋯π bonds giving rigidity to the molecule, while weak intermolecular N—H⋯N and C—H⋯π hydrogen bonds link the molecules into a two-dimensional structure.

Related literature

For the biological properties of pyrazole derivatives, see: Jia et al. (2004 ▶); Wei et al. (2006 ▶); Xia et al. (2007 ▶). For the synthesis and bioactivity evaluation of pyrazole derivatives, see: Zhang et al. (2008 ▶); Zhao et al. (2008 ▶); Tang et al. (2007 ▶).

Experimental

Crystal data

C₂₄H₂₁ClN₄O₂
M _r = 432.90
Monoclinic,
a = 10.0697 (12) Å
b = 5.1399 (6) Å
c = 40.990 (5) Å
β = 96.446 (2)°
V = 2108.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 298 K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.96, T _max = 0.98
10472 measured reflections
3699 independent reflections
2571 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.104
S = 1.03
3699 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010290/bg2246sup1.cif

e-65-0o865-sup1.cif^{(22.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010290/bg2246Isup2.hkl

e-65-0o865-Isup2.hkl^{(181.4KB, 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
C10—H10B⋯O1	0.97	2.35	2.876 (3)	114
C18—H18⋯O1	0.93	2.31	2.861 (3)	118
C12—H12⋯Cg1	0.93	2.74	3.354 (2)	125
N4—H4⋯N3ⁱ	0.86	2.59	3.406 (2)	159
C23—H23A⋯Cg2ⁱⁱ	0.97	2.71	3.571 (3)	149

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 and Cg2 are the centroids of the N1/N2/C1–C3 and C17–C22 rings, respectively.

Acknowledgments

This study was supported by the Science and Technology Developmental Project of Shandong Province (2008 GG10002034).

supplementary crystallographic information

Comment

Pyrazole framework plays an essential role in biologically active compounds. Many pyrazole derivatives are known to exhibit a wide range of biological properties such as anticoagulant (Jia et al., 2004), and antitumour (Wei et al., 2006; Xia et al. (2007)) activities. As part of our continuing project of the study on the synthesis and evaluation of pyrazole derivatives (Tang et al., 2007 and Zhao et al.,2008; Zhang et al., 2008), we report here the synthesis and crystal structure of the title compound C₂₄H₂₁ClN₄O₂. The pyrazole ring makes dihedral angles of 7.70 (11)°, 89.17 (11)° and 40.68 (11)° with the phenyl, pyridine and ethoxyphenyl rings, respectively. There are some intramolecular C—H···O and C—H···π bonds giving rigidity to the molecule (first three entries in Table 1), while weak intermolecular N—H···N and C—H···π hydrogen bonds (last two entries in Table 1) link the molecules into a 2D structure.

Experimental

1-(6-Chloropyridin-3-ylmethyl)-3-phenyl-1H-pyrazole-5-carboxylic acid (0.31 g, 1 mmol) and thionyl chloride (0.60 g, 5 mmol) were added to a flask with a condenser and heated to reflux for 4 h. After completion of the reaction (by TLC monitoring), the excess thionyl chloride was evaporated under reduced pressure. To the solution of the crude product, 1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-pyrazole-5-carbonyl chloride (0.332 g, 1 mmol), and triethylamine (0.15 g, 1 mmol) in dichloromethane (20 ml), the solution of 4-ethoxyaniline (0.14 g, 1 mmol) in dichloromethane (20 ml) was added and the mixture was stirred for 20 h at room temperature. Then the mixture was washed with water (20 ml x 3). After dried over anhydrous MgSO₄ the mixture was filtered and the filtrate obtained was concentrated under reduced pressure to obtain the corresponding crude product. The product was purified by column chromatography on silica gel using mixture of dichloromethane and ethyl acetate (10/1) as eluent (yield 43%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid dissolved in ethyl acetate/hexane at room temperature for 10 days.