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Powder X-ray diffraction of 1-(4-aminophenyl)-5,6-dihydro-3-(4-morpholinyl)-2(1H)-pyridinone, C15H19N3O2

Published online by Cambridge University Press:  29 October 2015

Qing Wang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Ya Ping Li
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Shan Shan Li
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Bin Tang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Hui Li*
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
*
a)Author to whom correspondence should be addressed. Electronic mail: lihuilab@sina.com.
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Abstract

X-ray powder diffraction data for 1-(4-aminophenyl)-5,6-dihydro-3-(4-morpholinyl)-2(1H)-pyridinone, C15H19N3O2, are reported [a = 14.877(4) Å, b = 5.893(6) Å, c = 18.984(3) Å, α = 90°, β = 122.298(3)°, γ = 90°, unit-cell volume V = 1406.86 Å3, Z = 4, and space group P21/c]. All measured lines were indexed and are consistent with the P21/c space group. No detectable impurities were observed.

Type
Rapid Communication
Copyright
Copyright © International Centre for Diffraction Data 2015 

1-(4-aminophenyl)-5,6-dihydro-3-(4-morpholinyl)-2(1H)-pyridinone is an intermediate in the synthesis of the anticoagulant, Apixaban (Watson et al., Reference Watson, Whiteside and Perry2011; Jiang and Ji, Reference Jiang and Ji2013). The sample was prepared using 3-(4-morpholinyl)-1-(4-nitrophenyl)-5,6-dihydro-2(1H)-pyridinone and was recrystallized in methanol and dried. The sample was then ground into powder (HPLC ≥ 98%, ρ = 1.283 g cm−3, T melt = 180–182 °C) and mounted on a flat zero background plate. X-ray powder diffraction measurement was performed at room temperature using an X'Pert PRO diffractometer (PANalytical Co., Ltd., The Netherlands) with a PIXcel 1D detector and Cu 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. 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, China). The X-ray powder diffraction pattern was pre-treated by subtracting the background, smoothing, and stripping off the 2 component. Automatic indexing results were obtained by X-Cell method (Neumann, Reference Neumann2003). The preliminary cell from indexing was refined using the Pawley method (Pawley, Reference Pawley1981). The refinement confirmed that the sample crystallizes in the monoclinic space group P21/c (14), with a = 14.877(4) Å, b = 5.893(6) Å, c = 18.984(3) Å, α = 90°, β = 122.298(3)°, γ = 90°, V = 1406.86 Å3, Z = 4, and ρ x  = 1.290 g cm−3. Figure 1 shows the Powder X-ray diffraction pattern of the compound.

Figure 1. Powder X-ray diffraction pattern of the compound.

ACKNOWLEDGEMENT

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).

SUPPLEMENTARY MATERIALS AND METHODS

The supplementary material for this article, can be found at http://dx.doi.org/10.1017/S088571561500072X

References

Jiang, J. and Ji, Y. (2013). “Alternate synthesis of apixaban (BMS-562247), an inhibitor of blood coagulation factor Xa,” Synth. Commun. 43(1), 7279.Google Scholar
Neumann, M. A. (2003). “X-Cell: a novel indexing algorithm for routine tasks and difficult cases,” J. Appl. Crystallogr. 36, 356365.Google Scholar
Pawley, G. S. (1981). “Unit-cell refinement from powder diffraction scans,” J. Appl. Crystallogr. 14(6), 357361.Google Scholar
Watson, J., Whiteside, G., and Perry, C. (2011). “Apixaban,” Drugs 71, 20792089.CrossRefGoogle ScholarPubMed
Figure 0

Figure 1. Powder X-ray diffraction pattern of the compound.

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