86847-59-8Relevant articles and documents
Copper- or Nickel-Enabled Oxidative Cross-Coupling of Unreactive C(sp3)-H Bonds with Azole C(sp2)-H Bonds: Rapid Access to β-Azolyl Propanoic Acid Derivatives
Tan, Guangying,Zhang, Luoqiang,Liao, Xingrong,Shi, Yang,Wu, Yimin,Yang, Yudong,You, Jingsong
, p. 4830 - 4833 (2017)
β-Azolyl propanoic acid derivatives are frequently found in biologically active molecules and pharmaceuticals. Here, we report the oxidative heteroarylation of unactivated C(sp3)-H bonds with azole C(sp2)-H bonds via copper or nickel catalysis with the aid of removable bidentate auxiliary, which provides a rapid pathway to β-azolyl propanoic acid derivatives. A variety of azoles such as oxazole, benzoxazole, thiazole, benzothiazoles, benzimidazole, purine, and even [1,2,4]triazolo[1,5-a]pyrimidine could be engaged in this protocol.
One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes
Ucar, Sefa,Dastan, Arif
supporting information, p. 4013 - 4022 (2020/09/21)
The transition metal-free coupling reactions of unactivated diazanaphthalenes were studied using only lithium tetramethylpiperidine (LiTMP) reagent. Symmetrical and nonsymmetrical bis-diazanaphthalenes were synthesized in moderate to high yield by homo- and cross-coupling of related monomers. In addition, the single-step synthesis of diquinoxalino [2,3-a: 2', 3'c] phenazine and 2,2': 3', 2″ - terquinoxaline using the appropriate equivalent amount of LiTMP was performed. The products were characterized by means of NMR spectroscopy and HRMS spectrometry.
6H-THIENO[2,3-E][1,2,4]TRIAZOLO[3,4-C][1,2,4]TRIAZEPINE DERIVATIVE
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Paragraph 0311-0313, (2020/05/07)
The 6H-thieno[2,3-e][1,2,4]triazolo[3,4-c][1,2,4]triazepine derivatives or salts thereof of the present invention have BRD4 inhibitory activity, and thus, they are useful as medicaments, in particular, as prophylaxis and/or therapeutic agents for diseases associated with BRD4.
Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters
Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.
supporting information, p. 482 - 487 (2019/01/04)
A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.
Design, Synthesis, and Biological Evaluation of 4-Quinoline Carboxylic Acids as Inhibitors of Dihydroorotate Dehydrogenase
Madak, Joseph T.,Cuthbertson, Christine R.,Miyata, Yoshinari,Tamura, Shuzo,Petrunak, Elyse M.,Stuckey, Jeanne A.,Han, Yanyan,He, Miao,Sun, Duxin,Showalter, Hollis D.,Neamati, Nouri
, p. 5162 - 5186 (2018/05/15)
We pursued a structure-guided approach toward the development of improved dihydroorotate dehydrogenase (DHODH) inhibitors with the goal of forming new interactions between DHODH and the brequinar class of inhibitors. Two potential residues, T63 and Y356, suitable for novel H-bonding interactions, were identified in the brequinar-binding pocket. Analogues were designed to maintain the essential pharmacophore and form new electrostatic interactions through strategically positioned H-bond accepting groups. This effort led to the discovery of potent quinoline-based analogues 41 (DHODH IC50 = 9.71 ± 1.4 nM) and 43 (DHODH IC50 = 26.2 ± 1.8 nM). A cocrystal structure between 43 and DHODH depicts a novel water mediated H-bond interaction with T63. Additional optimization led to the 1,7-naphthyridine 46 (DHODH IC50 = 28.3 ± 3.3 nM) that forms a novel H-bond with Y356. Importantly, compound 41 possesses significant oral bioavailability (F = 56%) and an elimination t1/2 = 2.78 h (PO dosing). In conclusion, the data supports further preclinical studies of our lead compounds toward selection of a candidate for early-stage clinical development.
Method for preparing 2-amino-3-hydroxymethylpyridine
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Paragraph 0032-0035; 0050; 0066, (2018/11/03)
The invention discloses a method for preparing 2-amino-3-hydroxymethylpyridine, and belongs to the field of chemical synthesis. 2-aminopyridine and pivaloyl chloride are used as initial reactants to form intermediate product 2-pivalamidopyridine under the action of triethylamine, after hydrogen extraction by use of n-butyllithium, dimethylformamide is added for hydroformylation, and target product2-amino-3-hydroxymethylpyridine can be obtained by reduction with sodium borohydride. Raw materials used in the method are low in cost, and the method is simple in operation, short in synthesis process, mild in reaction conditions, high in yield, and suitable for large-scale industrial production.
Diruthenium complexes with a 1,8-Naphthyridine-based Bis(silyl) supporting ligand: Synthesis and structures of complexes containing RuII2(μ-H)2 and RuI2 cores
Kusuma, Indra,Komuro, Takashi,Tobita, Hiromi
, p. 400 - 403 (2018/03/27)
We designed a novel naphthyridine-based supporting ligand involving two silyl coordinating moieties at 2,7-positions, t-BuNBSi, for the synthesis of dinuclear metal complexes. Reaction of a ligand precursor t-BuNBSi(H)2 (1) with Ru3(CO)12 gave a di-μ-hydridodiruthenium(II,II) complex (t-BuNBSi)Ru2(μ-H)2(CO)4 (2). Photoirradiation to 2 resulted in the formation of a diruthenium(I,I) complex (t-BuNBSi)Ru2(CO)6 (3). The SiRuRuSi linkage of 2 takes a zigzag arrangement, whereas that of 3 adopts a roughly linear one.
Synthesis method of N-heterocyclic acylamide derivative
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Paragraph 0090; 0091; 0092, (2019/01/14)
The invention discloses a synthesis method of an N-heterocyclic acylamide derivative. A reaction general formula is as shown in the specification. According to the synthesis method, an imidazo heterocyclic amine compound I is taken as a raw material; unde
Rhodium(III)-catalysed, redox-neutral C(sp2)-H alkenylation using pivalimide as a directing group with internal alkynes
Kathiravan, Subban,Nicholls, Ian A.
supporting information, p. 1 - 4 (2016/12/23)
In the presence of [RhCp?Cl2]2, N-pivaloyl anilines react with internal alkynes to give the corresponding 2-alkenylpivalimides under redox neutral conditions through C-H activation. This redox neutral hydroarylation, which does not require an external organic acid, unlocks a regioselective synthetic route to 2-alkenyl anilines and is generally applicable to diversely substituted electron rich and electron poor pivalimides.
A Chemoselective N-Arylation Reaction of 2-Aminopyridine Derivatives with Arynes
Cheng, Bin,Wei, Jian,Zu, Bing,Zhao, Jianfei,Wang, Taimin,Duan, Xiaoguang,Wang, Renqi,Li, Yun,Zhai, Hongbin
, p. 9410 - 9417 (2017/09/23)
A chemoselective N-arylation reaction of 2-aminopyridine derivatives with arynes in good to excellent yields has been described. The N-arylation products could be further applied to the facile construction of benzoisoquinuclidines and isoquinuclidines as
