Rebecca E. Deasy

Expanding the crystal landscape of isonicotinamide: concomitant polymorphism and co-crystallisation

Attempts to co-crystallise 3-arylbutanoic acid derivatives with isonicotinamide have led to co-crystals and novel polymorphs of the isonicotinamide co-former appearing under similar crystallisation conditions.

The Use of Co-crystals for the Determination of Absolute Stereochemistry: An Alternative to Salt Formation

Absolute stereochemistry of oils and viscous liquids can be difficult to determine. Co-crystallization involves generating a crystalline material consisting of more than one neutral compound. The combination of co-crystallization with both X-ray diffraction and chiral HPLC was particularly powerful in overcoming these difficulties for a series of chiral 3-arylbutanoic acids. Co-crystallization offers advantages over salt formation because co-crystals dissociate in solution, meaning identical HPLC conditions can be used for both the materials of interest and their co-crystals.

Telescoped Approach to Aryl Hydroxymethylation in the Synthesis of a Key Pharmaceutical Intermediate

An efficient synthetic approach leading to introduction of the hydroxymethyl group to an aryl moiety via combination of the Bouveault formylation and hydride reduction has been optimized using a rational, mechanistic-based approach. This approach enabled telescoping of the two steps into a single efficient process, readily amenable to scaleup.

Preparation of 2-Aminopyridoimidazoles and 2-Aminobenzimidazoles via Phosphorus Oxychloride-Mediated Cyclization of Aminoureas

The novel preparation of 2-aminopyridoimidazoles and 2-aminobenzimidazoles via the cyclization of (2-aminopyridin-3-yl)urea and (2-aminophenyl)urea substrates in the presence of phosphorus oxychloride is described. This methodology is demonstrated for a range of urea substrates with aminoimidazole products obtained in good yields and with excellent levels of purity.