Synthesis of Isomeric and Potent Impurities of the Triazole-Based Antifungal Drug Voriconazole

SUNDARAM, Dhanraj T. S. S.; MITRA, Jayati; ISLAM, Aminul; PRABAHAR, Koilpillai Joseph; VENKATESWARA RAO, Battula; PAUL DOUGLAS, Sanasi

doi:10.3797/scipharm.1501-13

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Article

6 March 2015

8 Pages

Synthesis of Isomeric and Potent Impurities of the Triazole-Based Antifungal Drug Voriconazole

and

Chemical Research and Development, APL Research Centre-II, Aurobindo Pharma Ltd., Survey No. 71 & 72, Indrakaran (V), Medak Dist.-502329, Andhra Pradesh, India

Department of Engineering chemistry, Andhra University College of Engineering (A), Andhra University, Visakhapatnam-530003, Andhra Pradesh, India

Author to whom correspondence should be addressed.

Sci. Pharm.2015, 83(3), 445-452;https://doi.org/10.3797/scipharm.1501-13

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Abstract

We describe the synthesis of two positional isomers and a desfluoro impurity of Voriconazole starting with Friedel–Crafts acylation of mono- and difluoro-benzene. These isomers are the crucial components in determining the quality of Voriconazole during its manufacturing from the key raw material, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one. All the prepared impurities were characterized by IR, ¹H-NMR, ¹³C-NMR, and mass spectral data.

Keywords:

Voriconazole; Impurity synthesis; Positional isomers; Chloroacetyl chloride

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