1196972-92-5Relevant articles and documents
PHENYL-SULFAMOYL.BENZOYC ACIDS AS ERAP1 MODULATORS
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Page/Page column 231, (2020/11/23)
The present invention relates to a compound of formula (I), or a pharmaceutically acceptable salt or hydrate thereof, wherein: the group X-Y is -NHSO2- or -SO2NH-; Z is a monocyclic aryl or heteroaryl group, each of which is optionally substituted by one ormore substituents selected from alkyl, cycloalkyl, halo, alkoxy, CN, haloalkyl and OH; R1 is H or alkyl; R2 is selected from COOH and a tetrazolyl group; R3 is selected from H, C land alkyl; R4 is selected from H and halo; R5 is selected from H, alkyl, haloalkyl, SO2-alkyl,Cl, alkoxy, OH, CN, hydroxyalkyl, alkylthio, heteroaryl, cycloalkyl, heterocycloalkyl andhaloalkoxy; R6 is H; R7 is selected from H, CN, haloalkyl, halo, SO2-alkyl,SO2NR12R13, heteroaryl, CONR10R11 and alkyl, wherein said heteroaryl group is optionallysubstituted by one or more substituents selected from alkyl, halo, alkoxy, CN, haloalkyl and OH; R8 is selected from H, alkyl, haloalkyl and halo; and R9 is H, alkyl or halo; R10 and R11 are each independently H or alkyl; and R12 and R13 are each independently H or alkyl. Further aspects of the invention relate to such compounds for use in the field of immuno- oncology and related applications. Another aspect of the invention relates to compounds of formulae (la) and (lb).
Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids
Deng, Tianning,Mazumdar, Wrickban,Ford, Russell L.,Jana, Navendu,Izar, Ragda,Wink, Donald J.,Driver, Tom G.
supporting information, p. 4456 - 4463 (2020/03/05)
A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.
I(III)-catalyzed oxidative cyclization - Migration tandem reactions of unactivated anilines
Deng, Tianning,Shi, Emily,Thomas, Elana,Driver, Tom G.
supporting information, p. 9102 - 9106 (2020/11/13)
An I(III)-catalyzed oxidative cyclization-migration tandem reaction using Selectfluor as the oxidant was developed that converts unactivated anilines into 3H-indoles is reported herein. The reaction requires as little as 1 mol % of the iodocatalyst and is mild, tolerating pyridine and thiophene functional groups, and the dependence of the diastereoselectivity of the process on the identity of the iodoarene or iodoalkane precatalyst suggests that the catalyst is present for the stereochemical determining C-N bond forming step.
Achieving High Ortho Selectivity in Aniline C-H Borylations by Modifying Boron Substituents
Smith, Milton R.,Bisht, Ranjana,Haldar, Chabush,Pandey, Gajanan,Dannatt, Jonathan E.,Ghaffari, Behnaz,Maleczka, Robert E.,Chattopadhyay, Buddhadeb
, p. 6216 - 6223 (2018/05/23)
High ortho selectivity for Ir-catalyzed C-H borylations (CHBs) of anilines results when B2eg2 (eg = ethylene glycolate) is used as the borylating reagent in lieu of B2pin2, which is known to give isomeric mixtures with anilines lacking a blocking group at the 4-position. With this modification, high selectivities and good yields are now possible for various anilines, including those with groups at the 2- and 3-positions. Experiments indicate that ArylN(H)Beg species are generated prior to CHB and support the improved ortho selectivity relative to B2pin2 reactions arising from smaller Beg ligands on the Ir catalyst. The lowest-energy transition states (TSs) from density functional theory computational analyses have N-H···O hydrogen-bonding interactions between PhN(H)Beg and O atoms in Beg ligands. Ir-catalyzed CHB of PhN(H)Me with B2eg2 is also highly ortho-selective. 1H NMR experiments show that N-borylation fully generates PhN(Me)Beg prior to CHB. The TS with the lowest Gibbs energy was the ortho TS, in which the Beg unit is oriented anti to the bipyridine ligand.
Cascade C-C and C-N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinolines
Borah, Ashwini,Gogoi, Pranjal
supporting information, p. 2200 - 2206 (2016/05/09)
A Pd-catalyzed cascade process has been developed for the synthesis of quinoline and phenanthridine derivatives from various β-chloro α,β-unsaturated aldehydes and 2-chloroaryl aldehydes, respectively, in good to high yields. The reaction proceeds through Pd-catalyzed cascade carbon-carbon and carbon-nitrogen bond formation in a single reaction vessel. The requisite β-chloro α,β-unsaturated aldehydes were efficiently synthesized from their corresponding carbonyl compounds. The use of the ligand Sphos with Pd(OAc)2 is crucial for the successful implementation of the present cascade process. This synthetic protocol is also applied for the gram-scale synthesis of a trispheridine alkaloid.
Rh2(II)-catalyzed ester migration to afford 3 H-indoles from trisubstituted styryl azides
Kong, Chen,Driver, Tom G.
, p. 802 - 805 (2015/04/27)
Rh2(II)-Complexes trigger the formation of 3H-indoles from ortho-alkenyl substituted aryl azides. This reaction occurs through a 4π-electron-5-atom electrocyclization of the rhodium N-aryl nitrene followed by a [1,2]-migration to afford only 3H-indoles. The selectivity of the migration is dependent on the identity of the β-styryl substituent.
A traceless directing group for C - H borylation
Preshlock, Sean M.,Plattner, Donald L.,Maligres, Peter E.,Krska, Shane W.,Maleczka Jr., Robert E.,Smith III, Milton R.
, p. 12915 - 12919 (2014/01/06)
Not a trace: Borylation of the nitrogen in nitrogen heterocycles or anilines provides a traceless directing group for subsequent catalytic C - H borylation. Selectivities that previously required Boc protection can be achieved; furthermore, the NBpin directing group can be installed and removed in situ, and product yields are substantially higher. Boc=tert-butoxycarbonyl, pin=pinacolato. Copyright
Rh2(II)-catalyzed selective aminomethylene migration from styryl azides
Kong, Chen,Jana, Navendu,Driver, Tom G.
supporting information, p. 824 - 827 (2013/03/29)
Rh2(II)-Carboxylate complexes were discovered to promote the selective migration of aminomethylenes in β,β-disubstituted styryl azides to form 2,3-disubstituted indoles. Mechanistic data are also presented that suggest that the migration occurs stepwise before diffusion of the iminium ion.
Rh2(II)-catalyzed intramolecular aliphatic C-H bond amination reactions using aryl azides as the N-atom source
Nguyen, Quyen,Sun, Ke,Driver, Tom G.
supporting information; experimental part, p. 7262 - 7265 (2012/06/16)
Rhodium(II) dicarboxylate complexes were discovered to catalyze the intramolecular amination of unactivated primary, secondary, or tertiary aliphatic C-H bonds using aryl azides as the N-atom precursor. While a strong electron-withdrawing group on the nitrogen atom is typically required to achieve this reaction, we found that both electron-rich and electron-poor aryl azides are efficient sources for the metal nitrene reactive intermediate.
RhII2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides
Pumphrey, Ashley L.,Dong, Huijun,Driver, Tom G.
supporting information; experimental part, p. 5920 - 5923 (2012/08/07)
Approaching all isomers: A range of α-, β- and δ-carbolinium ions are readily available from ortho-substituted aryl azides using a rhodium(II) carboxylate catalyst (see scheme). The carbolinium ions are readily reduced to afford tryptolines or deprotonated to access pyridoindoles. This [RhII2]-catalyzed C-H bond amination was used in the synthesis of (±)-horsfiline and neocryptolepine. esp=α,α,α',α'- tetramethyl-1,3-benzenedipropionate. Copyright
