50392-78-4Relevant academic research and scientific papers
Pyridine methylamine compound and preparation method thereof
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Paragraph 0132-0138, (2021/08/28)
The invention provides a pyridine methylamine compound and a preparation method thereof. The preparation method comprises the steps that tetrahydrofuran and sodium borohydride are sequentially added into a cyanopyridine compound, then an iodine-containing tetrahydrofuran solution is dropwise added, a reaction is conducted at the temperature of 20-30 DEG C, and after dropwise adding is completed, stirring is carried out continuously; after the reaction is finished, methanol is added for refluxing, extracting and spin-drying are carried out to obtain the pyridine methylamine compound; wherein a functional group in the cyanopyridine compound is selected from chlorine, bromine, methyl, ethyl, amino or hydrogen; according to the preparation method, high-temperature and high-pressure special equipment does not need to be used, so that the preparation method is relatively safe, and dangerous accidents such as explosion and fire disasters are avoided; besides, the preparation method is relatively environment-friendly, recycling treatment of hazardous waste (used Raney nickel) is not involved, the economic benefit is relatively high, borane generated by the synthesis method is converted into boric acid esters in the post-treatment process, the treatment cost is low, and the harm to the environment is much small.
Direct reductive amination of ketones with ammonium salt catalysed by Cp*Ir(iii) complexes bearing an amidato ligand
Dai, Zengjin,Pan, Ying-Min,Wang, Shou-Guo,Yin, Qin,Zhang, Xumu
supporting information, p. 8934 - 8939 (2021/11/04)
A series of half-sandwich Ir(iii) complexes1-6bearing an amidato bidentate ligand were conveniently synthesized and applied to the catalytic Leuckart-Wallach reaction to produce racemic α-chiral primary amines. With 0.1 mol% of complex1, a broad range of ketones, including aryl ketones, dialkyl ketones, cyclic ketones, α-keto acids, α-keto esters and diketones, could be transformed to their corresponding primary amines with moderate to excellent yields (40%-95%). Asymmetric transformation was also attempted with chiral Ir complexes3-6, and 16% ee of the desired primary amine was obtained. Despite the unsatisfactory enantio-control achieved so far, the current exploration might stimulate more efforts towards the discovery of better chiral catalysts for this challenging but important transformation.
The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst
B?umler, Christoph,Bauer, Christof,Kempe, Rhett
, p. 3110 - 3114 (2020/06/01)
The reductive amination of ketones and aldehydes by ammonia is a highly attractive method for the synthesis of primary amines. The use of catalysts, especially reusable catalysts, based on earth-abundant metals is similarly appealing. Here, the iron-catalyzed synthesis of primary amines through reductive amination was realized. A broad scope and a very good tolerance of functional groups were observed. Ketones, including purely aliphatic ones, aryl–alkyl, dialkyl, and heterocyclic, as well as aldehydes could be converted smoothly into their corresponding primary amines. In addition, the amination of pharmaceuticals, bioactive compounds, and natural products was demonstrated. Many functional groups, such as hydroxy, methoxy, dioxol, sulfonyl, and boronate ester substituents, were tolerated. The catalyst is easy to handle, selective, and reusable and ammonia dissolved in water could be employed as the nitrogen source. The key is the use of a specific Fe complex for the catalyst synthesis and an N-doped SiC material as catalyst support.
Reductive amination of ketonic compounds catalyzed by Cp*Ir(III) complexes bearing a picolinamidato ligand
Tanaka, Kouichi,Miki, Takashi,Murata, Kunihiko,Yamaguchi, Ayumi,Kayaki, Yoshihito,Kuwata, Shigeki,Ikariya, Takao,Watanabe, Masahito
, p. 10962 - 10977 (2019/09/03)
Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.
OXAZOLONE AND PYRROLIDINONE-SUBSTITUTED ARYLAMIDES AS P2X3 AND P2X2/3 ANTAGONISTS
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Page/Page column 24, (2010/12/31)
Compounds of the formula 1: or a pharmaceutically acceptable salt thereof, wherein, X, Y, R1, R2, R3, R4, R5, R6 and R7 are as defined herein. Also disclosed are methods of using the compounds for treating diseases associated with P2X3 and/or a P2X2/3 receptor antagonists and methods of making the compounds.
INDOLE, INDAZOLE AND BENZIMIDAZOLE ARYLAMIDES AS P2X3 AND P2X2/3 ANTAGONISTS
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Page/Page column 20, (2010/12/31)
Compounds of the formula I: or a pharmaceutically acceptable salt thereof, wherein, X, Y, Z, R1, R2, R3, R4 and R5 are as defined herein. Also disclosed are methods of using the compounds for treating diseases associated with P2X3 and/or a P2X2/3 receptor antagonists and methods of making the compounds.
Rapid, one-pot synthesis of α,α-disubstituted primary amines by the addition of Grignard reagents to nitriles under microwave heating conditions
Gregg, Brian T.,Golden, Kathryn C.,Quinn, John F.,Wang, Hong-Jun,Zhang, Wei,Wang, Ruifang,Wekesa, Francis,Tymoshenko, Dmytro O.
experimental part, p. 3978 - 3981 (2009/10/04)
A series of α,α-disubstituted amines have been prepared in a simple and efficient one-pot procedure by the addition of Grignard reagents to a series of aliphatic, aromatic, and heteroaromatic nitriles. Key to this reported procedure is the unprecedented addition of the Grignard reagent to the nitrile under heating by microwave irradiation which both significantly improves reaction yields and reduces reaction times. In general, the Grignard addition reaction is complete within 5-10 min at 100 °C followed by rapid reduction with sodium borohydride to give the target amines.
PYRIDAZINONE DERIVATIVES AND USE THEREOF AS P2X7 RECEPTOR INHIBITORS
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Page/Page column 122, (2009/06/27)
Novel pyridazinone compounds of formula (I), which inhibit the purinergic P2X7 receptor and are useful for prevention, therapy and improvement of inflammatory and immunological diseases.
3-SUBSTITUTED-[1,2,3]BENZOTRIAZINONE COMPOUNDS FOR ENHANCING GLUTAMATERGIC SYNAPTIC RESPONSES
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, (2008/12/07)
This invention relates to the prevention and treatment of cerebral insufficiency, including enhancement of receptor functioning in synapses in brain networks responsible for higher order behaviors. These brain networks are involved in cognitive abilities related to memory impairment, such as is observed in a variety of dementias and in imbalances in neuronal activity between different brain regions, as is suggested in disorders such as Parkinson's disease, schizophrenia and affective disorders. In a particular aspect, the present invention relates to compounds useful for treatment of such conditions, and methods of using these compounds for such treatment.
THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS
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Page 275, (2008/06/13)
Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).
