I. INTRODUCTION
Apixaban (Eliquis®) is a novel oral pyrazole-based direct FXa inhibitor; this drug was developed by Bristol-Myers Squibb and Pfizer to treat and prevent thrombotic disorder (Watson et al., Reference Watson, Whiteside and Perry2011). Since May 2011, Apixaban has been approved for venous thrombus embolism (VTE) prevention in adult elective hip or knee replacement patients in various countries, such as the USA, China, Brazil, Australia, New Zealand, and some European countries (Deeks, Reference Deeks2012). The title compound is an intermediate in the synthesis of the anticoagulant, Apixaban. Presently, the crystal structure of the title compound has not been reported.
II. EXPERIMENTAL
A. Sample preparation
The sample (Figure 1) was prepared using 1-(4-aminophenyl)-5,6-dihydro-3-(4-morpholinyl)-2(1H)-pyridinone (CAS: 1267610-26-3) (Wang et al., Reference Wang, Li, Li, Bin and Li2015; Ye and Wang, Reference Ye and Wang2015). The melting point and measured density of the title compound are 175-176 °C and 1.293 g cm−3, respectively. The title compound was recrystallized in methanol and dried. The sample was then ground into powder and mounted on a flat zero background plate.
Figure 1. Synthesis of the title compound.
B. Diffraction data collection and reduction
X-ray powder diffraction measurement was performed at room temperature using an X'Pert PRO diffractometer (PANalytical Co., Ltd., Netherlands) with a PIXcel 1D detector and CuKα radiation (generator setting: 40 kV and 40 mA). The diffraction data were collected over the angular range from 4° to 50°2θ with a step size of 0.013 13°2θ and a counting time of 30 ms step−1. Figure 2 shows the Powder X-ray diffraction (XRD) pattern of the compound.
Figure 2. X-ray powder diffraction pattern of the title compound using CuKα radiation.
The software package Material Studio 8.0 (Accelrys Co., Ltd., CA, USA) was used to process the data in the Analytical & Testing Center (Sichuan University, Chengdu, China). The X-ray powder diffraction pattern was pre-treated by subtracting the background, smoothing, and stripping off the Kα 2 component. Automatic indexing results were obtained by DICVOL91 method (Boultif and Louër, Reference Boultif and Louër1991). The indexing results were then refined with the type of Pawley (Pawley, Reference Pawley1981), which involves assigning the Miller indices (h, k, l) to each observed peak in the experimental powder XRD pattern.
III. RESULTS
The experimental raw data were indexed by DICVOL91 method. The figures of merit were achieved: F 25 = 121.8 (0.0062, 33) (Smith and Snyder, Reference Smith and Snyder1979) and M25 = 48.3 (de Wolff, Reference de Wolff1968). Pawley refinement results confirmed that the title compound is triclinic with space group P2 and unit-cell parameters: a = 9.511(5) Å, b = 18.539(2) Å, c = 5.645(3) Å, α = 90°, β = 101.813(1)°, γ = 90°, unit-cell volume V = 974.28 Å3, Z = 2, and ρ cal = 1.336 g cm−3. The values of 2θ obs, d obs, I obs, h, k, l, 2θ cal, d cal, I cal, Δ2θ are listed in Table I.
TABLE I. X-ray powder diffraction data for the title compound. The d-values were calculated using CuKα 1 radiation (λ = 1.540 56 Å).
SUPPLEMENTARY MATERIAL
To view supplementary material for this article, please visit http://dx.doi.org/10.1017/S0885715616000063
ACKNOWLEDGEMENTS
This work was supported by the Applied Basic Research Project of Sichuan Province (Grant No. 2014JY0042), the Testing Platform Construction of Technology Achievement Transform of Sichuan Province (Grant No. 13CGPT0049), and the National Development and Reform Commission and Education of China (Grant No. 2014BW011).
