Gilead Sciences, Inc.

Erik Rueden

Dustin S Siegel

Xianghong Wang

Edward Doerffler

Robert William Scott

Bruce Ross

Willard Lew

Lars V Heumann

Andrew W Waltman

Katrien Brak

Tiago Vieira

Robert Ronald Milburn

Andrew C Stevens

Sean Timothy Neville

Pavel Robertovich Badalov

Andrei Chtchemelinine

Mark Charles Whitcomb

Morin Mae Frick

Detian Gao

Silvio Campagna

Clarissa Tadeus

Brittanie Hoang

Lydia Wolfe

Chia-Yun Yu

Steven Donald Axt

Dustin Siegel

Provided are methods of preparing compounds and pharmaceutical compositions comprising a compound Formula VIII for treating Filoviridae virus infections. In one aspect, the compound of Formula VIII is formed from a reaction mixture comprising the compound of Formula IX, the compound of Formula X, a coupling agent such as magnesium chloride and a non-nucleophilic base such as diisopropylethylamine. The compound of Formula IX can be formed from a compound of Formula V and a cyanating agent. The compound of Formula V can be synthesized from a reaction mixture comprising a deprotonating agent such as phenylmagnesium chloride; a silylating agent such as chlorotrimethylsilane; a coupling agent such as isopropylmagnesium chloride, an additive such as LaCl-2LiCl, LaCl, CeCl, NdCl, or YCl; a compound of Formula VI; and 7-iodopyrrolo[2,1-f][1,2,4]triazin-4-amine. The compounds, compositions, and methods provided are particularly useful for the treatment of Marburg virus, Ebola virus and Cueva virus infections.

Methods for the preparation of ribosides

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San Mateo, CA, United States of America

Erik Rueden