444811-18-1

Basic information

• Product Name: 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine
• Synonyms: 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine
• CAS NO: 444811-18-1
• Molecular Formula: C₂₁H₂₁BrN₂O₂
• Molecular Weight: 413.30764
• Mol File: 444811-18-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine(444811-18-1)
• EPA Substance Registry System: 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine(444811-18-1)

Safety Data

• Hazardous Substances Data: 444811-18-1(Hazardous Substances Data)

Upstream product

• 1072-97-5 5-bromo-2-pyridylamine 
• 824-94-2 p-methoxybenzyl chloride 
• 664988-25-4 2-[(N,N-dibenzyl)amino]-5-bromopyridine 

Downstream Products

• 385449-77-4 2-(6-amino-pyridin-3-yl)-2-methyl-propionic acid 
• 246219-79-4 2-(6-amino-pyridin-3-yl)-2-methyl-propionic acid methyl ester 
• 1319054-99-3 C₂₅H₃₀N₂O₂ 
• 1319054-98-2 C₂₅H₂₈N₂O₃ 
• 1319054-97-1 C₂₅H₃₀N₂O₃ 
• 1072-97-5 5-bromo-2-pyridylamine 

Relevant articles and documents

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Compounds of formula (I) useful as tyrosine kinase 2 (Tyk2) inhibitors, pharmaceutical compositions containing these compounds, methods of using the pharmaceutical compositions in the treatment of various disorders related to the regulation of Tyk2 activi

Fragment-based identification of amides derived from trans-2-(pyridin-3-yl) cyclopropanecarboxylic acid as potent inhibitors of human nicotinamide phosphoribosyltransferase (NAMPT)

Potent, trans-2-(pyridin-3-yl)cyclopropanecarboxamide-containing inhibitors of the human nicotinamide phosphoribosyltransferase (NAMPT) enzyme were identified using fragment-based screening and structure-based design techniques. Multiple crystal structures were obtained of initial fragment leads, and this structural information was utilized to improve the biochemical and cell-based potency of the associated molecules. Many of the optimized compounds exhibited nanomolar antiproliferative activities against human tumor lines in in vitro cell culture experiments. In a key example, a fragment lead (13, KD = 51 μM) was elaborated into a potent NAMPT inhibitor (39, NAMPT IC 50 = 0.0051 μM, A2780 cell culture IC50 = 0.000 49 μM) which demonstrated encouraging in vivo efficacy in an HT-1080 mouse xenograft tumor model.

Conversion of 2-deoxy-D-ribose into 2-amino-5-(2-deoxy-β-D-ribofuranosyl)pyridine, 2′-deoxypseudouridine, and other C-(2′-deoxyribonucleosides)

The synthesis of 2-amino-5-(2-deoxy-β-D-ribofuranosyl)pyridine 2a, 2-amino-5-(2-deoxy-α-D-ribofuranosyl)-pyridine 23, 2-amino-5-(2-deoxy-β-D-ribofuranosyl)-3-methylpyridine 2b, 2-amino-5-(2-deoxy-α-D-ribofuranosyl)-3-methylpyridine 29 and 5-(2-deoxy-β-D-ribofuranosyl)-2,4-dioxopyrimidine [2′-deoxypseudouridine] 30a is described. These C-nucleosides are prepared either from 2-deoxy-3,5-O-(1, 1, 3, 3-tetraisopropyldisiloxan-1,3-diyl)-D-ribofuranose 15 or from 2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-D-ribono-1,4-lactone 16, which are themselves prepared from 2-deoxy-D-ribose 13. The sugar derivatives are first allowed to react with the appropriate 5-lithio-pyridine or 5-lithio-pyrimidine derivatives, which are prepared from 5-bromo-2-(dibenzylamino)pyridine 12a, 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine 12b, 5-bromo-2-dibenzylamino-3-methylpyridine 25 and 5-bromo-2,4-bis(4-methoxybenzyloxy)pyrimidine 33. The products from the reactions between the lithio-derivatives and the lactol 15 are cyclized under Mitsunobu conditions; the products from the reactions between the lithio-derivatives and the lactone 16 are first reduced with L-Selectride before cyclization, also under Mitsunobu conditions, In all cases, the β-anomers of the protected C-nucleosides are the predominant products. Finally, the separation of the α- and β-anomers and the removal of all of the protecting groups are described.