80194-70-3Relevant academic research and scientific papers
Combined preparation method of 2-cyano-3-chloro-5-trifluoromethylpyridine and succinonitrile
-
Paragraph 0024-0036, (2021/02/24)
The invention discloses a combined preparation method of 2-cyano-3-chloro-5-trifluoromethylpyridine and succinonitrile, and belongs to the field of organic chemistry. The method comprises the following steps: taking 2-fluoro-3-chloro-5-trifluoromethylpyridine and dichloroethane as raw materials, reacting in a potassium cyanide/sodium solution under the action of a phase transfer catalyst to obtaina mixed solution of 2-cyano-3-chloro-5-trifluoromethylpyridine and succinonitrile, layering, washing with water, and rectifying to obtain the 2-cyano-3-chloro-5-trifluoromethylpyridine with the content of more than 99% and the succinonitrile with the content of more than 99.9%. According to the method, the yield is high, the wastewater treatment is simple, byproducts are fully utilized, the yieldof the 2-cyano-3-chloro-5-trifluoromethylpyridine can reach 93%, and the yield of the succinonitrile can reach 95%.
3-chloro-2-cyano-5-trifluoromethyl pyridine preparation method
-
Paragraph 0026, (2017/04/28)
The invention discloses a 3-chloro-2-cyano-5-trifluoromethyl pyridine preparation method. The method includes steps: (1) dissolving 3-chloro-2-R-5-trifluoromethyl pyridine into a solvent A, adding an activating agent, performing heating reflux for 4-6h, cooling to 20-30 DEG C to obtain reaction liquid, filtering the reaction liquid to obtain a filter cake, and subjecting the filter cake to vacuum drying for 1-2h at 40-50 DEG C to obtain organic salt; (2) adding cyanide and the organic salt obtained at the step (1) into a solvent B and water, stirring for reaction for 2-3h at 0-80 DEG C to obtain mixed liquid, and standing the mixed liquid for layering to obtain an organic phase a; adding hydrochloric acid into the organic phase a to adjust pH to 2-4, standing for layering to obtain an acid water layer and an organic layer, and adding water to wash the organic layer until pH is 6-7, so that washed water and an organic phase b are obtained. By the preparation process, nitrile solvents such as acetonitrile and propionitrile are avoided while low-toxicity solvents such as dichloromethane hardly soluble in water are adopted, conception ingenuity is achieved, solvent recycling is realized, and accordingly production cost is reduced, and environment pollution is abated.
3 - chloro -5 - trifluoromethyl pyridine compounds and intermediates method (by machine translation)
-
Paragraph 0086; 0087; 0088; 0089; 0090; 0091; 0092-0094, (2017/07/20)
The invention discloses a 3 - chloro -5 - trifluoromethyl pyridine compound and preparation method of the midbody. The invention of the formula 3 a compound represented by the preparation method, comprising the following steps: organic solvent and water in the mixed solvent, under the action of the phase transfer catalyst, shown as 2 shown with the metal cyanide compounds of the substitution reaction, carbonized 3 compound of formula; further comprises the following steps: in the solvent, under the effect of the fluorination reagent, shown as 1 shown in the fluorination reaction of the compound, prepared states like the type 2 compound of formula; and can also be further comprises the following steps: under the action of the hydrogen and ethanol, shown as 3 shown in the Pinner reaction compound, then hydrolyzing the ester reaction, carbonized 4 compounds are shown. The invention of 3 - chloro -5 - trifluoromethyl pyridine compound preparation method of low cost, high production safety, simple operation, high yield, it is suitable for industrial production. (by machine translation)
A 2 - cyano - 3 - chloro - 5 - trifluoro methyl pyridine synthesis method (by machine translation)
-
Paragraph 0032; 0034, (2017/11/04)
The invention discloses a 2 - cyano - 3 - chloro - 5 - trifluoro methyl pyridine synthesis method, which belongs to the technical field of organic synthesis. The method includes the steps of: (1) to 2, 3 - dichloro - 5 - trifluoro methyl pyridine as raw material, in the solvent system is added in the catalyst, by fluorination synthesis of 2 - fluoro - 3 - chloro - 5 - trifluoro methyl pyridine, (2) in the step 1 of the 2 - fluoro - 3 - chloro - 5 - trifluoro methyl pyrrole cyanide reagent carbonitriding after adding, after the water washing, after the distillation, shall be 2 - cyano - 3 - chloro - 5 - trifluoro methyl pyridine. The purity of the product can reach 99.5%, the yield can be 90%, the reaction condition during the mild, easy to operate, and is suitable for large-scale production. (by machine translation)
Homogenous suspension of immunopotentiating compounds and uses thereof
-
Page/Page column 73; 74, (2016/09/12)
The present invention generally relates to homogeneous suspensions of small molecule immune potentiators (SMIPs) that are capable of stimulating or modulating an immune response in a subject in need thereof. The homogeneous suspensions may be used in combinations with various antigens or adjuvants for vaccine therapies.
"Nanorust"-catalyzed benign oxidation of amines for selective synthesis of nitriles
Jagadeesh, Rajenahally V.,Junge, Henrik,Beller, Matthias
, p. 92 - 96 (2015/02/19)
Organic nitriles constitute key precursors and central intermediates in organic synthesis. In addition, nitriles represent a versatile motif found in numerous medicinally and biologically important compounds. Generally, these nitriles are synthesized by traditional cyanation procedures using toxic cyanides. Herein, we report the selective and environmentally benign oxidative conversion of primary amines for the synthesis of structurally diverse aromatic, aliphatic and heterocyclic nitriles using a reusable "nanorust" (nanoscale Fe2O3)-based catalysts applying molecular oxygen.
Pyridine C-region analogs of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists
Ryu, Hyungchul,Seo, Sejin,Lee, Jee-Young,Ha, Tae-Hwan,Lee, Sunho,Jung, Aeran,Ann, Jihyae,Kim, Sung-Eun,Yoon, Suyoung,Hong, Mannkyu,Blumberg, Peter M.,Frank-Foltyn, Robert,Bahrenberg, Gregor,Schiene, Klaus,Stockhausen, Hannelore,Christoph, Thomas,Frormann, Sven,Lee, Jeewoo
, p. 101 - 108 (2015/03/05)
A series of pyridine derivatives in the C-region of N-((6-trifluoromethyl-pyridin-3-yl)methyl) 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides were investigated as hTRPV1 antagonists. The SAR analysis indicated that 6-difluorochloromethyl pyridine derivatives were the best surrogates of the C-region for previous leads. Among them, compound 31 showed excellent antagonism to capsaicin as well as to multiple hTRPV1 activators. It demonstrated stronganalgesic activity in the formalin test in mice with full efficacy and it blocked capsaicin-induced hypothermia in vivo.
COMPOUNDS AND COMPOSITIONS AS TLR ACTIVITY MODULATORS
-
Page/Page column 181, (2009/10/22)
The invention provides a novel class of compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with Toll-Like Receptors, including TLR7 and TLR8. In one aspect, the compounds are useful as adjuvants for enhancing the effectiveness of a vaccine (formula I) wherein: X3 is N; X4 is N Or CR3; X5 is -CR4=CR5.
2-AMINOPYRIDINE ANALOGS AS GLUCOKINASE ACTIVATORS
-
Page/Page column 76, (2008/12/04)
Provided are compounds that are useful in the treatment and/or prevention of diseases mediated by deficient levels of glucokinase activity, such as diabetes mellitus. Also provided are methods of treating or preventing diseases and disorders characterized by underactivity of glucokinase or which can be treated by activating glucokinase.
SUBSTITUTED NITROGEN-CONTAINING SIX-MEMBERED AMINO-HETEROCYCLES AS VANILLOID-1 RECEPTOR ANTAGONISTS FOR TREATING PAIN
-
Page/Page column 56, (2010/02/11)
The present invention provides a compound of formula (I): Y-J-NH-Z wherein: Y is a quinoline or isoquinoline optionally substituted with one or two substituents independently chosen from hydroxy, halogen, haloC1-4alkyl, C1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, nitro and amino; J is pyridine, pyridazine, pyrazine, pyrimidine or triazine optionally substituted with one or two substituents independently chosen from hydroxy, halogen, haloC1-4alkyl, C1-4alkyl, C3-5cycloalkyl, C1-4alkoxy, hydroxyC1-4alkyl, cyano, hydroxy, C1-4cycloalkoxy, C1-4alkylthio, haloC1-4alkoxy, nitro, Q, (CH2)pQ, NR2R3, -(CH2)pNR2R3 and -O(CH2)pNR2R3; wherein J is substituted at positions meta to each other by NH and Y; and Z is phenyl or pyridyl optionally substituted with one or two substituents independently selected from halogen, haloC1-4alkyl, C1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, nitro and amino; Q is phenyl, a five-membered heterocyclic ring containing one, two, three or four heteroatoms chosen from O, N and S, at most one heteroatom being O or S, or a six-membered heterocyclic ring containing one, two or three nitrogen atoms, optionally substituted by C1-4alkyl; each R2 and R3 is chosen from H and C1-4alkyl, or R2 and R3, together with the nitrogen atom to which they are attached, may form a six-membered ring optionally containing an oxygen atom or a further nitrogen atom, which ring is optionally substituted by C1-4alkyl or Q; p is 1, 2 or 3; or a pharmaceutically acceptable salt thereof; pharmaceutical compositions comprising it; its use in methods of therapy; use of it for manufacturing medicaments; and methods of using it to treat diseases requiring administration of a VR1 antagonist such as pain, cough, GERD and depression.
