130861-73-3Relevant articles and documents
HPK1 ANTAGONISTS AND USES THEREOF
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Paragraph 0936; 0937, (2021/03/19)
The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of HPK1, and the treatment of HPK1-mediated disorders.
Large-Scale Synthesis of 2-Chlorotetrahydroquinoline and 2-Chlorotetrahydroquinolin-8-one
Zong, Zhijian,Wu, Ke,Jin, Liqun,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
, p. 3675 - 3683 (2020/09/21)
An efficient large-scale preparation of 2-chlorotetrahydroquinoline with cyclohexanone and benzylamine as starting materials was developed and well optimized, in which benzyl-protected enamide was successfully cyclized and benzyl group was directly removed under Vilsmeier conditions. Azeotropic distillation provided 264 g of 2-chlorotetrahydroquinoline (79%) on a 2 mol scale of reaction without intermediate isolation. The downstream product 2-chlorotetrahydroquinolin-8-one was acquired through Boekelheide rearrangement, hydrolysis of acetate via NaBH 4reduction, and Anelli oxidation. With the developed procedure, the intermediates were not necessary to be isolated and 2-chlorotetrahydroquinolin-8-one was conveniently obtained with solvent slurry in 65% overall isolated yield in a four-step sequence.
Thermo-enhanced ring-opening polymerization of ?-caprolactone: The synthesis, characterization, and catalytic behavior of aluminum hydroquinolin-8-olates
Zhang, Qiurui,Zhang, Wenjuan,Rajendran, Natesan Mannangatti,Liang, Tongling,Sun, Wen-Hua
, p. 7833 - 7843 (2017/07/11)
A series of highly sensitive aluminum hydroquinolin-8-olates (C1-C8) was synthesized and characterized by 1H/13C NMR spectroscopy. The molecular structures of compounds C1, C3, C4, and C5 were confirmed by single crystal X-ray crystallography and demonstrated the binuclear form. In the presence of BnOH, all the aluminum complexes exhibited moderate to high activities towards the ring-opening polymerization of ?-CL at high temperatures, but quite low activities at ambient temperature. Microstructure analysis of the resultant polycaprolactones showed that the polymers were linear in nature with a BnO- end group. In addition, the mechanism was investigated by monitoring the 1H NMR and 27Al NMR of C1 and these results suggested that the complexes existed as dimeric species at low temperature and partly converted into active mononuclear species at higher temperatures, which was easily coordinated by BnOH to afford the active species for the ring-opening polymerization of ?-caprolactone.
IRAK4 INHIBITING AGENTS
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Page/Page column 112; 115, (2016/03/13)
Provided are compounds of Formula (I), or pharmaceutically acceptable salts thereof, and methods for their use and production.
A removing the hydroxy group of a benzyl protecting group method (by machine translation)
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Paragraph 0034, (2016/11/07)
The invention discloses a process for the removal of the hydroxyl group of a method of a benzyl protecting group, the method is as follows: to the hydroxy compound by the hydroxy group with protection of the benzyl protecting group of the benzyl compound as reaction substrate, in order to 2, the 3 [...] two chloro -5,6 the [...] two cyanato -1, the 4 [...] benzoquinone (DDQ) and phthalocyanine ferrous (Fe II Pc) as catalyst, in order to 4,4 '-bipyridine (4, the 4 [...] -bpy) as an auxiliary agent, with oxygen as the oxidizing agent, in an organic solvent in the reaction substrate, the oxygen pressure 0.3-0.6 MPa, temperature 60-120 °C reaction is carried out under the condition of, removing the hydroxy group of a benzyl protecting group obtain hydroxyl compound. With the traditional use of chemical metering of oxidation with DDQ for the protection, the consumption of DDQ in this invention is greatly reduced, reducing the cost of reaction; with DDQ as catalyst, metal oxide or metal salt is compared with oxidation of the oxidizing agent for the protection, the used in the present invention oxygen as the oxidizing agent, reduces the environmental costs. (by machine translation)
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone-catalyzed aerobic oxidation reactions via multistep electron transfers with iron(II) phthalocyanine as an electron-transfer mediator
Hong, Yiming,Fang, Tiantian,Li, Meichao,Shen, Zhenlu,Hu, Xinquan,Mo, Weimin,Hu, Baoxiang,Sun, Nan,Jin, Liqun
, p. 51908 - 51913 (2016/06/13)
A new biomimetic catalytic oxidation system which employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as the catalyst, molecular oxygen as the terminal oxidant and iron(ii) phthalocyanine (FeIIPc) as the electron-transfer mediator has been developed. This system can be applied for oxidative deprotection of PMB ethers, alcohol oxidation, aromatization and α,β-unsaturated aldehyde formation. After immobilizing FeIIPc on multi-walled carbon nanotubes, it can be reused without loss of activity.
Aerobic oxidative deprotection of benzyl-type ethers under atmospheric pressure catalyzed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/tert-butyl nitrite
Shen, Zhenlu,Sheng, Lili,Zhang, Xiaochu,Mo, Weimin,Hu, Baoxiang,Sun, Nan,Hu, Xinquan
, p. 1579 - 1583 (2013/03/28)
A facile and efficient protocol for the oxidative deprotection of benzyl-type ethers has been developed. The reaction was performed with catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite (TBN) under atmospheric pressure of O2. Under the optimal reaction conditions, a variety of p-methoxybenzyl (PMB), p-phenylbenzyl (PPB), and benzyl (Bn) ethers can be deprotected to their corresponding alcohols in excellent conversions and selectivities.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone ((DDQ)/tert-butyl nitrite/oxygen: A versatile catalytic oxidation system
Shen, Zhenlu,Dai, Jialiang,Xiong, Jie,He, Xijun,Mo, Weimin,Hu, Baoxiang,Sun, Nan,Hu, Xinquan
experimental part, p. 3031 - 3038 (2012/01/02)
A new catalytic oxidation system using catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite with molecular oxygen serving as the environmentally benign, terminal oxidant has been developed. This aerobic catalytic system was established for the selective oxidation of non-sterically hindered benzylic alcohols and electron-rich benzyl methyl ethers, and successfully extended to an application in the oxidative deprotection of PMB ethers to the alcohols in high selectivity. Copyright
Design and synthesis of new chiral pyridine-phosphite ligands for the copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones
Xie, Yinjun,Huang, Hanmin,Mo, Weimin,Fan, Xiangqun,Shen, Zhiqiang,Shen, Zhenlu,Sun, Nan,Hu, Baoxiang,Hu, Xinquan
experimental part, p. 1425 - 1432 (2009/12/04)
A series of new chiral pyridine-phosphite ligands have been prepared from (R)-pyridyl alcohols and BINOL-derived chlorophosphite, and successfully employed in the copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones. Using the simple and inexpensive CuBr2 as a precursor, the enantioselective additions to various substituted acyclic enones afforded products in high yields and good enantioselectivities (up to 92% ee).
Kinetic resolution of diols and pyridyl alcohols by cu(II)(borabox)- catalyzed acylation
Mazet, Clement,Roseblade, Stephen,Koehler, Valentin,Pfaltz, Andreas
, p. 1879 - 1882 (2007/10/03)
Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)-catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.
