1616100-97-0

Basic information

• Product Name: (R)-N-((2S,4R)-2-(2,4-difluorophenyl)-4-hydroxy-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane-2-sulfinamide
• Synonyms: (R)-N-((2S,4R)-2-(2,4-difluorophenyl)-4-hydroxy-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane-2-sulfinamide
• CAS NO: 1616100-97-0
• Molecular Weight: 383.462
• Mol File: 1616100-97-0.mol

Chemical Properties

• CAS DataBase Reference: (R)-N-((2S,4R)-2-(2,4-difluorophenyl)-4-hydroxy-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane-2-sulfinamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-((2S,4R)-2-(2,4-difluorophenyl)-4-hydroxy-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane-2-sulfinamide(1616100-97-0)
• EPA Substance Registry System: (R)-N-((2S,4R)-2-(2,4-difluorophenyl)-4-hydroxy-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane-2-sulfinamide(1616100-97-0)

Safety Data

• Hazardous Substances Data: 1616100-97-0(Hazardous Substances Data)

Upstream product

• 1616100-96-9 (R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide 
• 364-83-0 2',4'-difluoroacetophenone 
• 1585971-57-8 (R,E)-N-(1-(2,4-difluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide 

Downstream Products

• 1616100-99-2 N-(((2S,4R)-2-(2,4-difluorophenyl)-4-hydroxy-4-(pyrimidin-5-yl)butan-2-yl)carbamothioyl)benzamide 
• 1616100-50-5 (4S,6S)-4-(2,4-difluorophenyl)-4-methyl-6-(pyrimidin-5-yl)-5,6-dihydro-4H-1,3-thiazin-2-amine 

Relevant articles and documents

Discovery of S3-Truncated, C-6 Heteroaryl Substituted Aminothiazine β-Site APP Cleaving Enzyme-1 (BACE1) Inhibitors

Truncation of the S3 substituent of the biaryl aminothiazine 2, a potent BACE1 inhibitor, led to a low molecular weight aminothiazine 5 with moderate activity. Despite its moderate activity, compound 5 demonstrated significant brain Aβ reduction in rodents. The metabolic instability of 5 was overcome by the replacement of the 6-dimethylisoxazole, a metabolic soft spot, with a pyrimidine ring. Thus, truncation of the S3 substituent represents a viable approach to the discovery of orally bioavailable, brain-penetrant BACE1 inhibitors.

4,6-DIARYLAMINOTHIAZINES AS BACE1 INHIBITORS AND THEIR USE FOR THE REDUCTION OF BETA-AMYLOID PRODUCTION

Compounds of formula (I), including pharmaceutically acceptable salts thereof, are set forth herein: (I) wherein R1 and R2 are independently hydrogen, or -CH3; or R1 and R2 can join together in a ring by adding -(CH2)4-; R3 is hydrogen or C1-C3 al-kyl; Y and Z are independently a C6-C10- aryl group or a 5-10 membered heterocyclic group which can be further substituted with from 0-3 substituents selected from the group of halogen, hydroxy, amino, C1-4 alkylamino, C1-4 dialkylamino, halo C1-4 alkyl, CN, C1-C6, alkyl or cycloalkyl, C1-C6 alkoxy, -C=OC1-4 alkyl, -SO2C1-4 alkyl, and C2-C4 alkynyl; A is selected from the group of phenyl, ben-zyl, oxazolyl, thiazolyl, isoxazolyl, imidazolyl, pyrazolyl, pyridyl, pyrimidinyl, and pyrazinyl groups which can be further substituted with from 0-3 substituents selected from the group of halogen, hydroxy, amino, C1-4 alkylamino, C1-4 dialkylamino, haloC1-4 alkyl, hydroxyC1-6 alkyl, CN, C1-C6 alkyl or cycloalkyl, C1-C6 alkoxy, and C2-C4 alkynyl; L is -NHCO-, or is a single bond; and L and Z to-gether can be absent