28178-42-9Relevant academic research and scientific papers
1,1′-Dicarbodiimidoferrocenes: Synthesis, Characterization, and Group IV 1,1′-Bisguanidinateferrocene Complexes
Palomero, Orhi Esarte,Jones, Richard A.
, p. 2689 - 2698 (2019)
We report the two-step one-pot preparation of a series of bulky substituted 1,1′-dicarbodiimidoferrocene proligands. In solution the compounds achieve equilibrium with the corresponding 2,4-diimino-1,3-azetidine products which exhibit distinct spectroscopic and electrochemical features. Metalation of the carbodiimides with M(NMe2)4 (M = Zr, Hf) leads to fluxional six-coordinate compounds that exhibit intermediate Bailar twist features in solution and in the solid state. Coordination of the 2,4-diimino-1,3-diazetidines to Zr(NMe2)4 results in a metal-mediated carbodiimide metathesis into two zirconium guanidinate complexes, which can be rationalized by a two-step reaction mechanism.
Isocyanate deinsertion from κ1-O amidates: facile access to perfluoroaryl rhodium(i) complexes
Drover, Marcus W.,Schafer, Laurel L.,Love, Jennifer A.
, p. 19487 - 19493 (2015)
Reaction of the amidate ligand salt, Na[N(Dipp)C(O)C6F5] (1) (Dipp = 2,6-diisopropylphenyl) with [Rh(NBD)Cl]2 (NBD = norbornadiene) results in formation of the dirhodium(i) complex [Rh2{μ2-N,O-N(Dipp)C(O)C6F5}2(NBD)2] (2). Reaction of 2 with PCy3 at room temperature provides an equilibrium mixture of the geometric isomers (E/Z)-[Rh{κ1-O-N(Dipp)C(O)C6F5}(NBD)(PCy3)] (E/Z-3). Treatment of 2 with 3 equiv. of CNXyl (Xyl = 2,6-dimethylphenyl) gives the κ1-O complex [Rh{κ1-O-N(Dipp)C(O)C6F5}(CNXyl)3] (6) while use of 3 equiv. of PPh3 provides the κ2-complex [Rh{κ2-N,O-N(Dipp)C(O)C6F5}(PPh3)2] (8). For complex κ2-N,O8, an equilibrium results with free PPh3 giving the κ1-O complex [Rh{κ1-O-N(Dipp)C(O)C6F5}(PPh3)3] (9). Heating a tol-d8 solution of E/Z-3, 6, or 8/9 results in 2,6-diisopropylphenylisocyanate extrusion providing the corresponding [Rh]-C6F5 complex in good yield.
Stability and lifetime of quadruply hydrogen bonded 2-Ureido-4[1H]-pyrimidinone dimers
Soentjens, Serge H. M.,Sijbesma, Rint P.,Van Genderen, Marcel H. P.,Meijer
, p. 7487 - 7493 (2000)
2-Ureido-4[1H]-pyrimidinones are known to dimerize via a strong quadruple hydrogen bond array. A detailed study of the dimerization constant and lifetime of the dimer is presented here. Excimer fluorescence of pyrene-labeled 2-ureido-4[1H]-pyrimidinone 1b was used to determine a dimerization constant K(dim) of 6 x 107 M-1 in CHCl3, 1 x 107 M-1 in chloroform saturated with water, and 6 x 108 M-1 in toluene (all at 298 K). Under these conditions, the preexchange lifetime of the similar dimers of both 1d and 1e is 170 ms in CDCl3, 80 ms in wet CDCl3, and 1.7 s in toluene-d8, as determined by dynamic NMR spectroscopy. Association rate constants were calculated from the K(dim) values and the preexchange lifetimes. The resulting values are significantly lower than the diffusion-controlled association rate constants calculated using the Stokes-Einstein and the Debeije equations. This difference is ascribed to a tautomeric equilibrium of the monomer between the dimerizing 4[1H]-pyrimidinone and nondimerizing 6[1H]-pyrimidinone tautomers, which is unfavorable for dimerization.
SULFONIMIDAMIDE COMPOUNDS AS NLRP3 MODULATORS
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Paragraph 0432, (2021/07/31)
Described herein are compounds of Formula (I), Formula (I-A), and Formula (I-B), solvates thereof, tautomers thereof, and pharmaceutically acceptable salts of the foregoing, Further described herein are methods of inhibiting NLRP3 using said compounds, and methods of and compositions useful in treating NLRP3-dependent disorders.
NOVEL SULFONAMIDE CARBOXAMIDE COMPOUNDS
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Page/Page column 108; 109, (2019/01/21)
The present invention relates to compounds of formula (I) wherein Q is selected from O or S; R1 is a non-aromatic heterocyclic group comprising at least one ring nitrogen atom, wherein R1 is attached to the sulfur atom of the sulfonylurea group by a ring carbon atom, and wherein R1 may optionally be substituted; and R2 is a cyclic group substituted at the α-position, wherein R2 may optionally be further substituted. The present invention further relates to salts, solvates and prodrugs of such compounds, to pharmaceutical compositions comprising such compounds, and to the use of such compounds in the treatment and prevention of medical disorders and diseases, most especially by the inhibition of NLRP3.
ENHANCED BIOAVAILABILITY OF N-(2,6-BIS(1-METHYLETHYL) PHENYL)-N'-((1-(4-(DIMETHYLAMINO)-PHENYL)CYCLOPENTYL) METHYL)UREA HYDROCHLORIDE
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Page/Page column 17-18, (2017/02/09)
Methods for enhancing the bioavailability of N-(2,6-bis(1-methylethyl)phenyl)-N'-((1-(4-(dimethylamino)phenyl)cyclopentyl)-methyl)urea hydrochloride (ATR-101)through administration with food, and compositions and kits related thereto.
SOLID DRUG FORM OF N-(2,6-BIS(1-METHYLETHYL)PHENYL)-N'-((1-(4-(DIMETHYLAMINO)PHENYL)CYCLOPENTYL)METHYL)UREA HYDROCHLORIDE AND COMPOSITIONS, METHODS AND KITS RELATED THERETO
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Page/Page column 19; 20, (2016/04/26)
A novel solid drug form of N-(2,6-bis(1-methylethyl)phenyl)-N′-((1-(4-(dimethylamino)phenyl)cyclopentyl)methyl)urea hydrochloride (also referred to “ATR-101”) suitable for oral dosing, and to compositions, methods and kits relating thereto. ATR-101 has particular utility in the treatment of, for example, aberrant adrenocortical cellular activity, including adrenocortical carcinoma (ACC), congenital adrenal hyperplasia (CAH) and Cushing's syndrome.
Terminal imido rhodium complexes
Geer, Ana M.,Tejel, Cristina,Lopez, Jose A.,Ciriano, Miguel A.
supporting information, p. 5614 - 5618 (2014/06/10)
Compounds of the late transition metals with M≡X multiple bonds (X=CR2, NR, O) represent a synthetic challenge, partly overcome by preparative chemists, but with noticeable gaps in the second- and third-row elements. For example, there are no isolated examples of terminal imido rhodium complexes known to date. Described herein is the isolation, characterization, and some preliminary reactivity studies of the first rhodium complexes [Rh(PhBP3)(NR)] (PhBP3=PhB{CH2PPh 2}3) with a multiple and terminal Rh≡N bond. These imido compounds result from reactions of organic azides with the corresponding rhodium(I) complex having a labile ligand, and display a pseudo-tetrahedral core geometry with an almost linear Rh-N-C arrangement [177.5(2)°]] and a short Rh-N bond [1.780(2) A]. We also show that the Rh≡N bond undergoes protonation at the nitrogen atom or addition of H2, and also engages in nitrene-group transfer and cycloaddition reactions. A missing link: Terminal imido rhodium complexes with a Rh≡N multiple bond have been prepared, thus providing compounds which have been elusive to synthesis. Preliminary studies indicate rhodium imides are somewhat ambiphilic and can therefore undergo protonation at the nitrogen atom, as well as hydrogenation at the Rh≡N bond. These systems also engage in nitrene-group transfer and cycloaddition reactions.
Synthesis of ureas from titanium imido complexes using CO2 as a C-1 reagent at ambient temperature and pressure
Anderson, James C.,Moreno, Rafael Bou
body text, p. 1334 - 1338 (2012/04/10)
The coordinatively unsaturated 12-electron complex dichloro t-butylimido bispyridine titanium(iv) (2a) has been shown to react with CO2 to give N,N-bis-t-butyl urea. Two analogous sterically hindered coordinatively saturated 14-electron complexes dichloro t-butylimido trispyridine titanium(iv) (10a) and dichloro 2,6-(i-Pr)2phenylimido trispyridine titanium(iv) (10b) also gave their corresponding symmetrical ureas upon treatment with CO2. Further experiments support the intermediary of metallocycles formed from heterocumulene metathesis reactions. The unsymmetrical urea N-benzyl, N-t-butyl urea (11) was produced from treatment of 2,6-(i-Pr) 2phenylimido trispyridine titanium(iv) (10b) with CO2 and interception with BnNH2. Equimolar quantities of N,N- bistrimethylsilybenzylamine or N,N-bistrimethylsilyphenethylamine were shown to promote the reaction between t-butylimido bispyridine titanium(iv) (2a) and CO2 to give near quantitative yields of symmetrical urea. Other symmetrical ureas could be produced from TiCl4, amine and CO 2 in moderate to quantitative yields depending on the stoichiometry of amine present.
Mechanistic study of the palladium - Phenanthroline catalyzed carbonylation of nitroarenes and amines: Palladium - Carbonyl intermediates and bifunctional effects
Ragaini, Fabio,Gasperini, Michela,Cenini, Sergio,Arnera, Lucia,Caselli, Alessandro,Macchi, Piero,Casati, Nicola
supporting information; scheme or table, p. 8064 - 8077 (2010/03/31)
Palladium - phenanthroline complexes catalyze both the nitroarene carbonylation reaction and the amine oxidative carbonylation reaction to give, depending on the conditions, carbamates and ureas. There is evidence that the key step in both processes is the amine carbonylation. Here, we show that when the reaction is run in methanol key intermediate compounds have the general formula [Pd(RPhen)(COOMe)2] (1) (RPhen = l,10-phenanthroline or one of its substituted derivatives). The kinetics of the reaction of 1 with toluidine in the presence of a carboxylic or phosphorus acid is firstorder with respect to complex, acid, and toluidine. A CO atmosphere is also required for the reaction to proceed. Acid dimerization was shown not to be influential under the concentration conditions examined, but reaction between the acid and toluidine is not negligible and a correction has to be applied. Diphenylphosphinic acid is more effective than any carboxylic acid in promoting this reaction, as also observed under catalytic conditions. A series of equilibria and an irreversible acid-assisted proton transfer explain the observed data. Formation of an adduct between complexes of the kind 1 and CO was spectroscopically observed when RPhen = 2,9-Me2Phen. Several analogous complexes were also spectroscopically characterized and the X-ray structure of [Pd(2,9Me2Phen)Cl2(CO)] was solved. This shows an asymmetric coordination of the nitrogen ligand. Kinetic measurements were also conducted under catalytic conditions. An Eyring plot shows that the effect of the acidic promoter is to decrease the ?S * value, whereas no positive effect is observed on ?H*. A temperature-dependent correction for the reaction between the acid and aniline and phenanthroline present under the reaction conditions has to be applied. Comparison of the results obtained under stoichiometric and catalytic conditions strongly supports the view that 1 is involved even in the latter and that the acid is acting as a bifunctional promoter.
