Received 23 May 2011
aResearch and Development, API-PDT-03, Integrated Product Development (IPD), Innovation Plaza, Dr Reddy's Laboratories Ltd, Bachupally, Qutubullapur, Hyderabad 500 072, India, and bCentre of Excellence in Polymorphism and Particle Engineering, Integrated Product Development (IPD), Innovation Plaza, Dr Reddy's Laboratories Ltd, Bachupally, Qutubullapur, Hyderabad 500 072, India
Correspondence e-mail: firstname.lastname@example.org
The title compound, C14H12N4O3S, is an intermediate of Dexlansoprazole, a proton pump inhibitor (PPI) mainly developed for anti-ulcer activity. The absolute configuration of the title compound was determined as R. The crystal structure reveals that the molecules form chains along the b axis through N-HN and C-HO hydrogen-bonded dimers. These chains are connected via weak C-HO hydrogen bonds.
For the synthesis of the title compound, see: Kumar et al. (2009). For background to this class of anti-ulcer drugs, see: Arimori et al. (1998); Masa et al. (2001). For a related structure, see: Fujishima et al. (2002).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2006); program(s) used to solve structure: SIR2004 (Burla et al. 2005); program(s) used to refine structure: CRYSTALS (Betteridge et al. 2003); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: CrystalStructure.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2104 ).
The authors are grateful to the management of IPDO-API and Dr Reddy's Laboratories Ltd for encouragement. Many thanks to our colleagues Srinivas Gangula, Naredla Anitha and Baddam Sudhakar Reddy for their support in the overall process development.
Arimori, K., Yasuda, K., Katsuki, H. & Nakana, M. (1998). J. Pharm. Pharmacol. 50, 1241-1245.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Fujishima, A., Aoki, I. & Kamiyama, K. (2002). US Patent No. 6462058B1.
Jacobson, R. (1998). REQAB. Private communication to Rigaku Corporation, Tokyo, Japan.
Kumar, K. N., Nagaraju, M., Srinivas, G., Kumar, N. U., Anitha, N., Reddy, B. S., Vishwasrao, P. S., Kumar, T. A., Reddy, P. S., Gulabrao, S. S., Ashok, S. & Varma, M. S. (2009). Patent WO 2009/117489 A1.
Masa, K., Hamada, A., Arimori, K., Fujii, J. & Nakano, M. (2001). Biol. Pharm. Bull. 24, 274-277.
Molecular Structure Corporation & Rigaku (2006). CrystalStructure. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.