Merck + Co., Inc.

J Christopher McWilliams

David Askin

Peter Emmanuel Maligres

Marjorie See Waters

Jennifer A Cowen

Kevin Campos

Artis Klapars

Lisa F Frey

Robert Wenslow

Yaling Wang

Joseph D Armstrong, Iii

Cheng-Yi Chen

Andrey V Peresypkin

Alex Minhua Chen

C Scott Shultz

Debra J Wallace

The present invention is directed to a practical process for the preparation of an enamide (II) by palladium catalyzed coupling of a primary amide (IV) with a compound of structural formula (III), as shown below: As well as to crystalline forms of a compound produced by this process, in particular, an anhydrous crystal form, Form B, and crystalline solvates falling into three patterns, Type 1, Type 2, and Type 3, and crystalline intermediate compounds produced in the process. Still further, the present invention relates to the stereoselective reduction of the tetrasubstituted enamide (II) to the corresponding amide (I).

Formation of tetra-substituted enamides and stereoselective reduction thereof

The present invention is directed to a process for synthesizing 1,5 disubstituted imidazoles with biaryl components of the formula (I):

Process for synthesizing biaryl inhibitors of farnesyl-protein transferase

The present invention is directed to a process for synthesizing 1,5-disubstituted imidazoles, which are useful in the preparation of farnesyl-protein transferase inhibitors.

Process for making 1,5-disubstituted imidazoles

The instant invention provides a homologation process for making a zincate homoenolate from a carbon bound enolate zincate, by treating the carbon bound enolate zincate with an alkoxy lithium reagent. The homologation step can be coupled with a homoaldol reaction, as well as with other transmetallation reactions, in a one pot process. The zincate homoenolate is a useful intermediate in the preparation of a variety of different end-products, such as HIV protease inhibitors and renin inhibitors.

Tandem asymmetric transformation process

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Basking Ridge, NJ, United States of America

J Christopher McWilliams