124700-69-2Relevant academic research and scientific papers
A facile preparation of n2-arylisocytosines
Spychala, Jaroslaw
, p. 1943 - 1949 (1997)
N2-Arylisocytosines were obtained in good yields varying from 59 to 96% by a simple two-step process starting from 2-thiouracil via readily accessible 2-(methylthio)pyrimidin-4(3H)-one.
A new and efficient protocol for the synthesis of the key intermediate of palbociclib
Li, Shuting,Yang, Wanfeng,Ji, Min,Cai, Jin,Chen, Junqing
, p. 14 - 19 (2019)
A new and efficient synthesis of 6-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)-pyrido[2,3-d]pyrimidin-7(8H)-one, a key intermediate of Palbociclib, starting from thiouracil was described. This protocol involved methylation, nucleophilic substitution, bromination, nucleophilic substitution, Heck reaction, ring closure, oxidation, and bromination to afford a key intermediate of Palbociclib with approximately 35% overall yield. The advantages of this developed synthetic strategy included improved overall yield, inexpensive starting materials, and readily controllable and cleaner reaction conditions.
Sulfenyl Ynamides in Gold Catalysis: Synthesis of Oxo-functionalised 4-aminoimidazolyl Fused Compounds by Intermolecular Annulation Reactions
Arce, Elsa M.,Lamont, Scott G.,Davies, Paul W.
, p. 2503 - 2509 (2020)
Functionalised N-heterocyclic pyridinium N-aminides have been designed and synthesised to evaluate a nitrenoid-based annulation strategy into imidazole-fused oxo-substituted frameworks of importance to medicinal and agrochemical discovery programmes. Sulfenyl substituted ynamides were identified as privileged reactants affording productive gold-catalysed annulation reactions with these and other nitrenoids. This annulation method provides selective and efficient access into geminally amino-sulfenyl substituted nitrogen heterocycles under mild reaction conditions. (Figure presented.).
Scaffold hopping in discovery of HIV-1 non-nucleoside reverse transcriptase inhibitors: From CH(CN)-DABOs to CH(CN)-dapys
Chen, Fen-Er,Li, Ting-Ting,Pannecouque, Christophe,Zhuang, Chun-Lin,de Clercq, Erik
, (2020/04/10)
Scaffold hopping is a frequently-used strategy in the development of non-nucleoside reverse transcriptase inhibitors. Herein, CH(CN)-DAPYs were designed by hopping the cyano-methylene linker of our previous published CH(CN)-DABOs onto the etravirine (ETR). Eighteen CH(CN)-DAPYs were synthesized and evaluated for their anti-HIV activity. Most compounds exhibited promising activity against wild-type (WT) HIV-1. Compounds B4 (EC50 = 6 nM) and B6 (EC50 = 8 nM) showed single-digit nanomolar potency against WT HIV-1. Moreover, these two compounds had EC50 values of 0.06 and 0.08 μM toward the K103N mutant, respectively, which were comparable to the reference efavirenz (EFV) (EC50 = 0.08 μM). The preliminary structure-activity relationship (SAR) indicated that introducing substitutions on C2 of the 4-cyanophenyl group could improve antiviral activity. Molecular docking predicted that the cyano-methylene linker was positioned into the hydrophobic cavity formed by Y181/Y188 and V179 residues.
BF3·SMe2 for Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles
S?derstr?m, Marcus,Zamaratski, Edouard,Odell, Luke R.
, p. 5402 - 5408 (2019/06/27)
Herein, a general, solvent-free and straightforward thiomethylation of electron deficient heterocycles using BF3·SMe2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF3·SMe2 towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non-malodorous reagent while the discovery of novel chemical transformations using BF3·SMe2 provides fundamental new insights into the reactivity of this commonly employed reagent.
A Palumbo vial preparation method of the key intermediate (by machine translation)
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Paragraph 0008; 0010, (2018/03/24)
The invention discloses a Palumbo Xilin key intermediate 6 - bromo - 2 - methyl sulfonyl - 8 - cyclopentyl - 5 - methyl pyridine and (2, 3 - d) pyrimidine - 7 (8 H) - ketone. The method uses the thiourea pyrimidine as the starting material, by methylation, chloro, bromo synthesis of 5 - bromo - 4 - chloro - 2 - methylthio-pyrimidine, then with the cyclopentamine alkylation, with 2 - butenoic acid by the heck reaction, then the intramolecular acylation reaction for the synthesis of 2 - methylthio - 8 - cyclopentyl - 5 - methyl pyridine and (2, 3 - d) pyrimidine - 7 (8 H) - one, finally with the NBS reaction for the preparation of 6 - bromo - 2 - methyl sulfonyl - 8 - cyclopentyl - 5 - methyl pyridine and (2, 3 - d) pyrimidine - 7 (8 H) - one. The preparation process of the present invention short step, not using the dangerous process, simple and convenient operation, low cost of raw materials, to meet the using requirements of the people. (by machine translation)
Industrial synthesis method of rilpivirine and intermediate compound
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Paragraph 0028; 0038-0040, (2017/10/07)
The invention discloses an industrial synthesis method of rilpivirine. A compound as shown in a formula I and compound hydrochloride as shown in a formula VI react to obtain rilpivirine. The invention further discloses an intermediate compound as shown in the formula I and a synthesis method of the intermediate compound. Compared with the prior art, the synthesis method is simple to operate, mild in condition, high in yield and purity and suitable for industrial production.
A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2- d ]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines
Mishina, Maria S.,Ivanov, Alexander Yu.,Lobanov, Pavel S.,Dar'In, Dmitrii V.
supporting information, p. 2851 - 2862 (2016/08/30)
An efficient approach for the synthesis of fused 2-aminopyrroles via geminal enediamines and π-deficient 1,2-dihaloarenes is presented. The two-step methodology includes aromatic nucleophilic substitution of the activated halogen of dihaloarene with enediamine C-nucleophilic center followed by Cu-catalyzed intramolecular N-arylation. This approach allows access to a variety of 2-amino-6-nitroindoles and 6-aminopyrrolo[3,2-d]pyrimidines (including N-mono- and N,N-disubstituted) in moderate and good yields under mild conditions.
HETEROCYCLIC COMPOUND
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Paragraph 0766, (2015/03/03)
The present invention provides an agent for the prophylaxis or treatment of autoimmune diseases (e.g., psoriasis, rheumatoid arthritis, inflammatory bowel disease, Sjogren's syndrome, Behcet's disease, multiple sclerosis, systemic lupus erythematosus etc.) and the like, which has a superior Tyk2 inhibitory action. The present invention relates to a compound represented by the formula wherein each symbol is as defined in the specification, or a salt thereof.
INHIBITORS OF IRAK4 ACTIVITY
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Page/Page column 41, (2014/05/07)
The present invention relates to compounds which modulate interleukin-l (IL-1 ) receptor-associated kinase 4 (IRAK4) and are useful in the prevention or treatment of inflammatory, cell proliferative and immune-related conditions and diseases. Specifically, provided herein are inhibitors of IRAK4 of Formula I and pharmaceutical compositions comprising such inhibitors, as well as methods therewith for treating IRAK4-mediated or -associated conditions or diseases.
