5663-56-9Relevant articles and documents
Method for synthesizing α - isopropyl -3 and 4 -methoxyacetonitrile
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Paragraph 0005-0006; 0020-0022; 0027-0029; 0034-0036, (2021/09/29)
The invention belongs to the technical field of organic synthesis, and particularly discloses a synthesis method α - isopropyl -3 and 4 -methoxyacetonitrile. To 3, 4 - dimethoxyphenyl acetic acid as a raw material, 2 - (3, 4 - dimethoxyphenyl) acetamide is formed through acylation reaction, and 3, 4 -methoxyphenyl acetonitrile are obtained by dehydration, and α - isopropyl -3 and 4 -methoxyacetonitrile are formed by alkylation reaction. The starting materials are cheap and easily available. The method avoids the use of highly toxic crisis reagents, is mild in reaction conditions, simple in post-treatment, short in synthetic route and high in yield.
Substrate Profiling of the Cobalt Nitrile Hydratase from Rhodococcus rhodochrous ATCC BAA 870
Mashweu, Adelaide R.,Chhiba‐Govindjee, Varsha P.,Bode, Moira L.,Brady, Dean
, (2020/01/13)
The aromatic substrate profile of the cobalt nitrile hydratase from Rhodococcus rhodochrous ATCC BAA 870 was evaluated against a wide range of nitrile containing compounds (>60). To determine the substrate limits of this enzyme, compounds ranging in size from small (90 Da) to large (325 Da) were evaluated. Larger compounds included those with a biaryl axis, prepared by the Suzuki coupling reaction, Morita–Baylis–Hillman adducts, heteroatomlinked diarylpyridines prepared by Buchwald–Hartwig crosscoupling reactions and imidazo[1,2a]pyridines prepared by the Groebke–Blackburn–Bienaymé multicomponent reaction. The enzyme active site was moderately accommodating, accepting almost all of the small aromatic nitriles, the diarylpyridines and most of the biaryl compounds and Morita–Baylis–Hillman products but not the Groebke–Blackburn–Bienaymé products. Nitrile conversion was influenced by steric hindrance around the cyano group, the presence of electron donating groups (e.g., methoxy) on the aromatic ring, and the overall size of the compound.
AN IMPROVED PROCESS FOR THE SYNTHESIS OF IVABRADINE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS
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Page/Page column 17; 18, (2019/11/12)
: Disclosed herein is an improved process for the preparation of Ivabradine and pharmaceutically acceptable salts thereof. The invention more particularly disclosesthe synthesis of key intermediates viz.,(S)-N-[(4,5-dimethoxybenzocydobut-l-yl)-methyl]-N- (methyl)amine hydrochloride of Formula-II and 3-(3-Iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzapin-2-one of Formula-III, and its use in industrial synthesis of Ivabradine and pharmaceutically acceptable salts thereof.
Ti-superoxide catalyzed oxidative amidation of aldehydes with saccharin as nitrogen source: Synthesis of primary amides
Kamble, Rohit B.,Mane, Kishor D.,Rupanawar, Bapurao D.,Korekar, Pranjal,Sudalai,Suryavanshi, Gurunath
, p. 724 - 728 (2020/01/23)
A new heterogeneous catalytic system (Ti-superoxide/saccharin/TBHP) has been developed that efficiently catalyzes oxidative amidation of aldehydes to produce various primary amides. The protocol employs saccharin as amine source and was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, catalyst reusability and operational simplicity are the main highlights. A possible mechanism and the role of the catalyst in oxidative amidation have also been discussed.
Synthesis of β-hydroxyamides through ruthenium-catalyzed hydration/transfer hydrogenation of β-ketonitriles in water: Scope and limitations
González-Fernández, Rebeca,Crochet, Pascale,Cadierno, Victorio
, p. 90 - 101 (2019/06/18)
A cascade process for the straightforward one-pot conversion of β-ketonitriles into β-hydroxyamides is presented. The process, that proceeds in water employing the arene-ruthenium(II) complex [RuCl2(η6-p-cymene){P(4-C6H4F)2Cl}] as catalyst in combination with sodium formate, involves the initial hydration of the β-ketonitrile substrates to generate the corresponding β-ketoamide intermediates, which subsequently undergo the transfer hydrogenation (TH) of the carbonyl group. Employing a family of forty different β-ketonitriles, featuring diverse substitution patterns, the scope and limitations of the process have been established.
Pd(OAc)2-catalyzed lactonization of arylacetamides involving oxidation of C-H bonds
Uemura, Takeshi,Igarashi, Takuya,Noguchi, Moe,Shibata, Kaname,Chatani, Naoto
supporting information, p. 621 - 623 (2015/05/20)
The reaction of arylacetamides that contain a quinolin-8-ylmethylamine as the directing group with PhI(OAc)2, in the presence of Pd(OAc)2 as the catalyst, results in lactonization to give γ-lactones, the formation of which involves activation of the ortho C-H bonds, with concomitant cleavage of the directing group.
Synthesis, characterization and cardioprotective activity of some novel benzotriazole and pyrazole derivatives
Gudaparthi, Vijayalakshmi,Bharathi,Panda, Jagadeesh
experimental part, p. 5323 - 5330 (2012/07/28)
A series of N-(1-(1H-benzo[d]) [1,2,3]triazol-1-yl)-2,2-dimethyl propyl)-2-(substituted phenyl) acetamide derivatives and methyl 5-((4- (2,5-disubstituted phenyl) furan-2 carboxylate derivatives are prepared from different substituted aryl carboxylic acids, phenyl acetic acid and cinnamic acid, respectively. All the synthesized compounds are investigated for cardioprotective activity by ischemia reperfusion method, while all the compounds show significant activity.
Discovery and biological evaluation of novel cyanoguanidine P2X7 antagonists with analgesic activity in a rat model of neuropathic pain
Perez-Medrano, Arturo,Donnelly-Roberts, Diana L.,Honore, Prisca,Hsieh, Gin C.,Namovic, Marian T.,Peddi, Sridhar,Shuai, Qi,Wang, Ying,Faltynek, Connie R.,Jarvis, Michael F.,Carroll, William A.
experimental part, p. 3366 - 3376 (2010/04/03)
We disclose the design of a novel series of cyanoguanidines that are potent (IC50 ? 10-100 nM) and selective (≥100-fold) P2X7 receptor antagonists against the other P2 receptor subtypes such as the P2Y2, P2X4, and P2X3. We also found that these P2X7 antagonists effectively reduced nociception in a rat model of neuropathic pain (Chung model). Particularly, analogue 53 proved to be effective in the Chung model, with an ED50 of 38 μmol/kg after intraperitoneal administration. In addition compound 53 exhibited antiallodynic effects following oral administration and maintained its efficacy following repeated administration in the Chung model. These results suggest an important role of P2X7 receptors in neuropathic pain and therefore a potential use of P2X7 antagonists as novel therapeutic tools for the treatment of this type of pain.
Study of the microwave-assisted hydrolysis of nitriles and esters and the implementation of this system in rapid microwave-assisted Pd-catalyzed amination
Van Baelen, Gitte,Maes, Bert U.W.
, p. 5604 - 5619 (2008/09/21)
Microwave-assisted hydrolysis of benzonitriles and methyl benzoates has been studied using a toluene/concd aq KOH two phase system in the presence and absence of phase transfer catalyst. Conditions to allow and avoid smooth hydrolysis could be identified. Based on the latter, the first microwave protocol which allows the rapid Pd-catalyzed amination of aliphatic amines with chlorobenzenes containing sensitive functional groups has been developed.
Antihypertensive dihydropyridines with 1,4,4-trisubstitution
Kukla,Breslin,Gill
, p. 223 - 228 (2007/10/02)
Dihydropyridines with 1,4,4-trisubstitution were synthesized and tested for antihypertensive activity in a spontaneously hypertensive rat model. This substitution pattern on the dihydropyridine nucleus differs markedly from that found most active in the structure-activity relationship established for nifedipine-like compounds. However, some were found to significantly lower blood pressure at testing doses (30 mg/kg, ip and 100 mg/kg, po) for up to 24 h. Methyl 1,4-dihydro-4,4-dimethyl-1-pyridinepropanoate (2-1), for example, lowered blood pressure 71 mmHg at 30 mg/kg, ip and the effect endured for greater than 24 h. Unlike prototypical dihydropyridines such as nifedipine, these compounds did not seem to have any effect on calcium channels.
