18344-51-9

Usage

Chemical Properties

White to yellow crystalline powder.

InChI:InChI=1/C6H7N3O2/c1-4-2-5(9(10)11)3-8-6(4)7/h2-3H,1H3,(H2,7,8)/p+1

Upstream product

• 1603-40-3 3-methylpyridin-2-ylamine 
• 18344-53-1 3-methyl-2-nitraminopyridine 
• 3599-89-1 propionamidine hydrochloride 
• 14080-32-1 5-nitropyrimidine 
• 7664-93-9 sulfuric acid 
• 6960-20-9 3-methyl-5-nitropyridine 

Downstream Products

• 99989-57-8 N-(3-methyl-5-nitro-[2]pyridyl)-benzenesulfonamide 
• 21901-34-8 2-hydroxy-3-methyl-5-nitropyridine 
• 22280-56-4 2-chloro-3-methyl-5-nitropyridine 
• 1010108-59-4 methyl 4-[[4-(methoxycarbonyl)benzoyl](3-methyl-5-nitro-2-pyridinyl)amino]carbonylbenzenecarboxylate 
• 106070-58-0 2,5-diamino-3-methylpyridine 
• 1266336-13-3 di-tert-butyl (3-methyl-5-nitro-pyridin-2-yl)imidodicarbonate 
• 1266336-04-2 tert-butyl (2-{(1S,2S)-2-[1-(5-chloro-pyrimidin-2-yl)-piperidin-4-yl]-cyclopropyl}-ethyl)-(3-methyl-5-nitro-pyridin-2-yl)-carbamate 
• 1230637-09-8 tert-butyl (3-methyl-5-nitropyridin-2-yl)carbamate 
• 70-58-6 5-fluoropyridine-3-carboxamide 
• 402-66-4 5-fluoropyridine-3-carboxylic acid 
• 350-04-9 5-fluoro-3-pyridinecarbonyl chloride 
• 3430-19-1 5-methylpyridin-3-amine 
• 407-21-6 5-methyl-3-fluoropyridine 

Relevant academic research and scientific papers

Heterocyclic FXR binding compounds

The present invention relates to compounds which bind to the NR1H4 receptor (FXR) and act as agonists or partial agonists of the NR1H4 receptor (FXR). The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds, and to a process for the synthesis of said compounds.

Selective vicarious nucleophilic amination of 3-nitropyridines

Nine 3-nitropyridine compounds and 4-nitroisoquinoline have been aminated in the 6-position (for 4-nitroisoquinoline in the 1-position) by vicarious nucleophilic substitution reactions. Two amination reagents were used, hydroxylamine and 4-amino-1,2,4-triazole. The yields were from moderate to good. Use of hydroxylamine gave an easy work-up procedure by which almost pure product was obtained directly, but 4-amino-1,2,4-triazole gave better yields of the aminated product for some of the substrates. By this, a general method for the preparation of 3- or 4-substituted-2-amino-5-nitropyridines was obtained.

SYNTHESES WITH AROMATIC NITRAMINES, VI SUBSTITUENT EFFECT IN THE PHOTOLYTIC REARRANGEMENT OF NITRAMINOPYRIDINES

All isomeric ring-substituted methyl-2-nitraminopyridines, both 3-nitro- and 5-nitro-2-nitraminopyridines, 5-chloro- and 3-carboxy-2-nitraminopyridines, as well as 3,5-dibromo-2-nitraminopyridine were photolyzed in methanol by irradiation with a low-pressure mercury lamp (253.7 nm).Preference was generally noted for the migration of the side-chain nitro group to the vicinal β-position. 3,5-Dibromo-2-nitraminopyridine gave both 2-amino-3,5-dibromopyridine and 3,5-dibromopyridine-2-one.The ratio of the preparative and quantum yields of the two products were 2.5 and 3.0, respectively.

Ring Transformations in Reactions of Heterocyclic Compounds with Nucleophiles. Conversion of 5-Nitropyrimidine into 2-Substituted 5-Nitropyrimidine and 2-Amino-5-nitropyridines by Amidines

The reaction of 5-nitropyrimidine (1) with benzamidine, pivalamidine, acetamidine, propionamidine, α-phenylacetamidine, O-methylisourea hydrochlorides, and cyanamide in ethanolic solution in the presence of triethylamine has been investigated.It was found that reaction of 1 with alkyl(aryl) amidines, having no active methylene groups attached to the amidine moiety (pivalamidine, benzamidine), exclusively formed the corresponding 2-substituted 5-nitropyrimidines in good yields.With acetamidine and propionamidine, in addition to the formation of the 2-substituted 5-nitropyrimidines, the formation of 2-amino-5-nitropyridines also was observed; with α-phenylacetamidine a 2-amino-5-nitropyridine derivative exclusively was obtained.The reaction of 1 with both O-methylisourea and cyanamide leads to 2-amino-5-nitropyrimidine.These reactions provide new examples of degenerate ring transformations of the pyrimidine ring system and of the ring transformation of pyrimidines into pyridines.