10167-97-2Relevant articles and documents
Synthesis of 2-amino-5-hydroxypyridine via demethoxylation
Cheng,Liu
, p. 1403 - 1404 (2016)
A convenient and efficient four-step synthesis of 2-amino-5-hydroxypyridine can be achieved by protective reaction of 2-amino-5-bromopyridine in the presence of 2,5-hexanedione to yield 5-bromo-2-(2,5-dimethyl-1H-pyrrol-1yl)pyridine, methoxylation with sodium methylate to give 5-methoxy-2-(2,5-dimethyl-1H-pyrrol-1yl)pyridine, deprotective reaction with hydroxylamine hydrochloride to produce 2-amino-5-methoxypyridine and demethylation with 95 % H2SO4 to afford the title compound in an overall yield of 45 %.
Synthesis and Antiinflammatory Activity of Metabolites of Piroxicam
Lombardino, Joseph G.
, p. 39 - 42 (1981)
Four possible pyridine monohydroxylated metabolites of the antiinflammatory agent piroxicam have been synthesized for comparison with a natural pyridine-hydroxylated metabolite of this compound.In addition, another metabolite of piroxicam, derived from dehydration of the parent drug, has been made and characterized.The antiinflammatory activity of these compounds and four other known metabolites of piroxicam has been measured in the carrageenan-induced rat paw edema model and all are found to be less active than piroxicam itself.
Effect of Terminal Alkylation of Aryl and Heteroaryl Hydrazines in the Fischer Indole Synthesis
Schmidt, Michael A.
, (2021/04/12)
The effect of alkylation on the terminal position of aryl and heteroaryl hydrazines in the Fischer indole synthesis was examined. Compared to their unalkylated counterparts, reactions using alkylated hydrazines provided indole products with higher yields and faster rates. The reactions can be conducted at lower temperatures and are compatible with acid-sensitive functionality. The terminally alkylated hydrazines were readily prepared by a new two-step sequence and held as stable hydrazinium salts. The mild formation of the salts along with the favorable Fischer indole reaction conditions highlights the potential of this approach in later-stage synthetic use.
BICYCLIC KINASE INHIBITORS AND USES THEREOF
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, (2021/11/06)
The invention relates to kinase inhibitors, in particular inhibitors of protein kinases including the SIK-family, CSF1R, HCK, TEK-family, BRK, ABL, KIT and/or their mutants. Although structurally similar to other bicyclic kinase inhibitors, the kinase inhibitors of the invention are distinctive; possessing a particular class of heterocyclic moiety. Such kinase inhibitors can display one or more certain properties distinct to their structurally similar kinase inhibitors. The kinase inhibitors of the invention or pharmaceutical compositions comprising them may be used in the treatment of a disorder or condition, such as a proliferative disorder, for example, a leukaemia or solid tumour. In particular, these and other structurally related kinase inhibitors may be used in the treatment of a proliferative disorder - such as a mixed phenotype acute leukaemia (MPAL) - characterised by (inter-alia) the presence of MEF2C protein, a human chromosomal translocation at 11q23, and/or a KMT2A fusion oncoprotein. The kinase inhibitors or pharmaceutical compositions of the invention may be used topically to modulate skin pigmentation in a subject, for example to impart UV protection and reduce skin cancer risk.
Simple Nickel Salts for the Amination of (Hetero)aryl Bromides and Iodides with Lithium Bis(trimethylsilyl)amide
Martinez, Gabriel Espinosa,Nugent, Joseph W.,Fout, Alison R.
supporting information, p. 2941 - 2944 (2018/09/21)
Recent developments in the chemistry of C-N bond formation and the synthesis of anilines have allowed for the use of first-row transition metals to catalyze these transformations. Much of the progress in this area has been driven by comprehensive screening for privileged/tailored ligands, which can be costly and not readily available in a research laboratory setting. In this communication we report a protocol in which simple nickel salts catalyze the C-N cross-coupling reaction between (hetero)aryl bromides and iodides with lithium bis(trimethylsilyl)amide without the need for any additive ligand. This method is amenable to low nickel catalyst loadings (1%) as well as gram-scale reactions. Because of the good functional group tolerance and compatibility with heterocyclic moieties, this method is useful for academic laboratory settings where access to tailored ligands and noble-metal catalysts could be challenging.
PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS
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Page/Page column 51; 54, (2017/04/11)
The present invention relates to a catalytic method for the conversion of amide-containing compouds by means of a build-in directing group and upon the action of a heteronucleophilic compound (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or a thiol (RSH)) in the presence of a metal catalyst to respectively esters, thioesters, carbonates, thiocarbonates and to what is defined as amide-containing compounds (such as carboxamides, urea, carbamates, thiocarbamates). The present invention also relates to these amide-containing compounds having a build-in directing group (DG), as well as the use of such directing groups in the catalytic directed cleavage of N-DG amides with the use of heteronucleophiles (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or thiol (RSH)).
1 -(CYCLOPENT-2-EN-1 -YL)-3-(2-HYDROXY-3-(ARYLSULFONYL)PHENYL)UREA DERIVATIVES AS CXCR2 INHIBITORS
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Page/Page column 131, (2015/12/18)
The invention relates to 1-(3-sulfonylphenyl)-3-(cyclopent-2-en-1-yl)urea derivatives, and their use in treating or preventing diseases and conditions mediated by the CXCR2 receptor. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.
Ligandless copper-catalyzed coupling of heteroaryl bromides with gaseous ammonia
Fantasia, Serena,Windisch, Johannes,Scalone, Michelangelo
supporting information, p. 627 - 631 (2013/04/11)
A range of different N- and S-containing heterocyclic bromides can be efficiently coupled with gaseous ammonia in the presence of copper(II) acetylacetonate [Cu(acac)2] as catalyst and in the absence of additional ligands. Unstable aminothiophenes and aminobenzothiophenes can be further reacted in situ to afford functionalized derivatives. Copyright
NOVEL COMPOUND HAVING AFFINITY FOR AMYLOID
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Page/Page column 9; 24, (2010/08/09)
A compound effective as a probe targeting amyloid for image diagnosis and a reagent comprising the compound for detecting amyloid deposited on a biological tissue are provided. Provided are a compound represented by the following formula (1): wherein R1, R2 and R3 independently represent a group selected from the group consisting of a hydrogen, hydroxyl group, alkyl substituent with 1 to 4 carbon atoms, alkoxy substituent having alkyl chain with 1 to 4 carbon atoms and halogen substituent, excluding the case where two or more of the substituents R1, R2 and R3 are hydrogen, R4 is a group selected from the group consisting of a hydrogen, hydroxy group, alkoxy substituent having alkyl chain with 1 to 4 carbon atoms and halogen substituent, and m is an integer of 1 to 4, provided that at least one of R1, R2, R3 and R4 represents a radioactive halogen substituent, and a reagent comprising the same.
NOVEL COMPOUND HAVING AFFINITY FOR AMYLOID
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Page/Page column 15; 27, (2010/08/09)
A compound effective as a probe targeting amyloid for image diagnosis and a reagent comprising the compound for detecting amyloid deposited on a biological tissue are provided. Provided are a compound represented by the following formula (1): wherein R1 is a group selected from the group consisting of a halogen substituent, alkyl substituent with 1 to 4 carbon atoms, alkoxy substituent having alkyl chain with 1 to 4 carbon atoms and hydroxyl group, R2 is a group selected from the group consisting of a cyano substituent, alkyl substituent with 1 to 4 carbon atoms and halogen substituent, is a group selected from the group consisting of a hydroxyl group, halogen substituent and substituent represented by the following formula: (wherein R4 is a hydrogen, halogen substituent or hydroxyl group, and m is an integer of 1 to 4), provided that a t least one of R1, R2, R3 and R4 represents a radioactive halogen, and a reagent comprising the same.
