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Pharmaceutical impurity identification: a case study using a multidisciplinary approach.
TLDR
A multidisciplinary team approach to identify pharmaceutical impurities is presented, and the following discussion describes how the information gained from each analytical technique was brought together in a complementary fashion to elucidate a final structure.
Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling.
The title salts are more stable and more easily handled than DAST and Deoxo-Fluor and can be prepared in a safer and more cost-effective manner.
Use of DOE for Rapid Development of a Red-Al Reduction Process for the Synthesis of 3,4-Isopropylidenedioxypyrrolidine Hydrotosylate
Statistical design of experiments (DOE) was used to rapidly optimize Red-Al reduction of an imide to produce, after deprotection and salt formation, 3,4-isopropylidenedioxypyrrolidine hydrotosylate
Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling†,‡
TLDR
These reagents are typically more selective than DAST and Deoxo-Fluor and exhibit superior performance by providing significantly less elimination side products.
Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents
TLDR
Aminodifluorosulfinium tetrafluoroborates are easy handled crystalline salts that show enhanced thermal stability over dialkylaminosulfur trifluorides, are storage-stable, and unlike DAST and Deoxo-Fluor do not react violently with water.
Carbonyldiimidazole-mediated Lossen rearrangement.
TLDR
Carbonyldiimidazole (CDI) was found to mediate the Lossen rearrangement of various hydroxamic acids to isocyanates and represents a green alternative to standard processing conditions for the Curtius and Hofmann rearrangements.
Palladium and Raney nickel catalyzed methanolic cleavage of stable borane-amine complexes.
TLDR
Palladium and Raney nickel were found to catalyze the methanolysis of borane-amine adducts and strongly complexed amines can now be liberated by simple treatment with Pd/C or Raney Ni in methanol.
Cu-catalyzed N-arylation of oxazolidinones: an efficient synthesis of the kappa-opioid receptor Agonist CJ-15161.
TLDR
An efficient method for intermolecular N-arylation of oxazolidinones using catalytic copper in the presence of a bidentate ligand is reported and a short, scalable synthesis of CJ-15,161 is reported.
Streamlined Processes for the Synthesis of a Farnesyl Transferase Inhibitor Drug Candidate
As part of a fast-paced oncology program, quinolinone 1 was discovered and developed as a potent inhibitor of farnesyl transferase for the treatment of cancer. The initial synthesis, which suffered
Mild and direct conversion of quinoline N-oxides to 2-amidoquinolines with primary amides.
TLDR
A simple, one-pot procedure is described for the direct conversion of quinoline N-oxides to alpha-amidoquinolines with primary amides, complimentary to the Abramovich reaction, which is limited to the introduction of secondary amides via imidoyl chlorides.
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