2-tert-Butyl-4-chloro-5-[4-(2-fluoro­eth­oxy)benz­yloxy]pyridazin-3(2H)-one

Huihui Jing; Tiantian Mou; Xianzhong Zhang

doi:10.1107/S1600536812020491

. 2012 May 12;68(Pt 6):o1707. doi: 10.1107/S1600536812020491

2-tert-Butyl-4-chloro-5-[4-(2-fluoroethoxy)benzyloxy]pyridazin-3(2H)-one

Huihui Jing ^a, Tiantian Mou ^a, Xianzhong Zhang ^a,^*

PMCID: PMC3379300 PMID: 22719498

Abstract

In the title compound, C₁₇H₂₀ClFN₂O₃, the dihedral angle between the pyridazine and benzene rings is 41.37 (10)°. In the crystal, there are no significant intermolecular interactions present. The terminal –CH₂F group is disordered over two sets of sites with an occupancy ratio of 0.737 (2):0.263 (2).

Related literature

For details of the synthesis, see: Mou et al. (2010 ▶, 2012 ▶). For possible applications of the title compound as a myocardial perfusion imaging agent for positron emission tomography (when labelled with ¹⁸F), see: Mou et al. (2011 ▶); Mou et al. (2012 ▶). graphic file with name e-68-o1707-scheme1.jpg

Experimental

Crystal data

C₁₇H₂₀ClFN₂O₃
M _r = 354.80
Triclinic,
a = 8.7170 (14) Å
b = 9.5850 (16) Å
c = 11.8524 (19) Å
α = 110.475 (2)°
β = 107.185 (2)°
γ = 96.424 (3)°
V = 860.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 150 K
0.47 × 0.38 × 0.35 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.892, T _max = 0.918
4337 measured reflections
3090 independent reflections
2788 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.094
S = 1.05
3090 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020491/aa2046sup1.cif

e-68-o1707-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020491/aa2046Isup4.hkl

e-68-o1707-Isup4.hkl^{(151.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812020491/aa2046Isup3.cml

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

Acknowledgments

We thank Dr Xuebin Deng, from the College of Chemistry, Beijing Normal University, for his kind help with the diffraction data collection. This work was supported by the National Natural Science Foundation of China (20871020), Beijing Natural Science Foundation (2092018) and the Fundamental Research Funds for the Central Universities.

supplementary crystallographic information

Comment

Myocardial uptake of the pyridaben analogues, which is correlated with blood flow, makes them potential myocardial perfusion imaging (MPI) agents for the positron emission tomography (PET) when labeled with ¹⁸F (Mou et al., 2010; Mou et al., 2011; Mou et al., 2012). Thus, the development of pyridaben analogues may lead to discover new valuable PET MPI agents.

The molecular structure of the title compound (measured at 150 K) is shown in Fig. 1. The dihedral angle between the pyridazine ring and the benzene ring is 41.37 (10)°. The terminal CH₂F group is disordered between two positions with occupancies 0.737 (2) for C1F1 and 0.263 (2) for C1AF1A.

Experimental

The synthesis route is shown in Fig. 2. The solution of tert-butylammonium fluoride (1 mmol in 1 ml tetrahydrofuran) was stirred in a stream of nitrogen at 110 °C to remove the solvent. Then 2-tert-butyl-4-chloro-5-(4-(2-tosylethoxy-ethoxy)-benzyloxy)-2H-pyridazin-3-one (compound I, 0.30 mmol in 3 ml anhydrous CH₃CN) was added to the above evaporation residue, and refluxed for 40 min at 90 °C. After concentration under reduced pressure, the residue was chromatographed over a column of silica gel and eluted with the mixture of dichloromethane and methanol (100:1). The product was obtained as white solid. The product was then recrystallized from the mixture of hexane and methanol (2:1) yielding colorless crystals of the title compound suitable for the single-crystal X-ray diffraction.