- PROCESS FOR PREPARATION OF LASMIDITAN
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The present invention relates to a process for the preparation of lasmiditan, a compound of formula I, or pharmaceutically acceptable salts thereof, the process comprising reacting a compound of formula IX with N-methoxymethylamine or salt thereof to obtain a compound of formula VII; reacting the compound of formula VII with a compound of formula XIV to obtain lasmiditan or salts thereof.
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Paragraph 0162
(2020/06/01)
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- Preparation method of 2-amino substituted six-membered nitrogen-containing heterocycle complex
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The invention discloses a preparation method of a 2-amino substituted six-membered nitrogen-containing heterocycle complex. The preparation method comprises the following steps: mix 2-fluorine substituted six-membered nitrogen-containing heterocycle complex and amidine hydrochloride salt compound, and then react under the action of a alkaline substance to obtain a 2-amino substituted six-memberednitrogen-containing heterocycle complex. Preferably, the 2-amino substituted six-membered nitrogen-containing heterocycle complex is a 2-amino pyridine compound, a 2-aminopyrimidine compound or a 2-aminopyrazine compound. Compared with the prior art, the method has the advantages of simple synthesis conditions, less reaction steps, mild reaction conditions, low cost of the catalyst used, less waste discharge and good functional group tolerance.
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Paragraph 0061; 0062
(2019/02/08)
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- AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS
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In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.
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Paragraph 0257
(2018/03/25)
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- Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride
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Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of a high yield, high chemoselectivity and wide substrate adaptability. The results suggest that other N-heterocycles containing fluorine substituents can also complete the reaction via these reaction conditions and yield the target products.
- Li, Yibiao,Huang, Shuo,Liao, Chunshu,Shao, Yan,Chen, Lu
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supporting information
p. 7564 - 7567
(2018/11/02)
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- Non-deprotonative primary and secondary amination of (hetero)arylmetals
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Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl-as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or Erecting groups. This one-pot transformation allows unprecedented functional group tolerance and it is wellsuited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper (l) salt is required.
- Zhou, Zhe,Ma, Zhiwei,Behnke, Nicole Erin,Gao, Hongyin,Kürti, László
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supporting information
p. 115 - 118
(2017/05/16)
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- Efficient synthesis of aminopyridine derivatives by copper catalyzed amination reactions
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A copper(i) catalyzed amination reaction utilizing aqueous ammonia and operating under mild conditions is presented. This method was employed for the efficient synthesis of various aminopyridine derivatives bearing electron withdrawing and electron donating groups. The Royal Society of Chemistry 2010.
- Elmkaddem, Mohammed K.,Fischmeister, Cedric,Thomas, Christophe M.,Renaud, Jean-Luc
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supporting information; experimental part
p. 925 - 927
(2010/06/12)
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- Direct synthesis of primary arylamines via C-N cross-coupling of aryl bromides and triflates with amides
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Aryl halides and triflates are coupled with primary amides to give the corresponding arylamines in the presence of a palladium catalyst, a suitable ligand, and a base. The catalyst system performs well for a large number of different substrates at 100-150 °C without solvent, and with low catalyst levels (0.12 mol % Pd). Nicotinamide might be useful as a nitrogen source in the Pd-catalyzed amination reaction.
- Romero,Harrak,Basset,Orúe,Pujol
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experimental part
p. 1951 - 1956
(2009/07/11)
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- Cooperative effect of a classical and a weak hydrogen bond for the metalInduced construction of a self-assembled β-turn mimic
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A novel metal-induced template for the self-assembly of two independent phosphane ligands by means of unprecedented multiple noncovalent interactions (classical hydrogen bond, weak hydrogen bond, metal coordination, π-stacking interaction) was developed and investigated. Our results address the importance and capability of weak hydrogen bonds (WHBs) as important attractive interactions in selfassembling processes based on molecular recognition. Together with a classical hydrogen bond, WHBs may serve as promoters for the specific self-assembly of complementary monomeric phosphane ligands into supramolecular hybrid structures. The formation of an intermolecular C-H...N hydrogen bond and its persistence in the solid state and in solution was studied by X-ray crystal analysis, mass spectrometry and NMR spectroscopy analysis. Further evidence was demonstrated by DFT calculations, which gave specific geometric parameters for the proposed conformations and allowed us to estimate the energy involved in the hydrogen bonds that are responsible for the molecular recognition process. The presented template can be regarded as a new type of self-assembled β-turn mimic or supramolecular pseudo amino acid for the nucleation of β-sheet structures when attached to oligopeptides.
- Laungani, Andy C.,Keller, Manfred,Slattery, John M.,Krossing, Ingo,Breit, Bernhard
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scheme or table
p. 10405 - 10422
(2010/04/05)
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- Synthesis of (NH)m(NMe)4-m-bridged calix[4]pyridines and the effect of NH bridge on structure and properties
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(Chemical Equation Presented) The (NH)m(NMe)4-m- bridged calix[4]pyridines (m = 1-4) 19-23 were synthesized in excellent yields from deprotection of N-allyl groups of (NAllyl)m(NMe) 4-m-bridged calix[4]pyridine derivatives 8 and 15-18, which were prepared in moderate yields by macrocyclic 2+2 and 1+3 coupling reactions between simple diamino- and dibromo-substituted fragments. In the solid state, (NH)m(NMe)4-m-bridged calix[4]pyridines adopted different 1,3-alternate conformations due to mainly the formation of varied conjugation systems of bridging NH units with their neighboring pyridines. In solution, all (NH)m(NMe)4-m-bridged calix[4]pyridines were very fluxional and the rates of interconversion of various conformational structures were very rapid relative to the NMR time scale. While (NH)4-bridged calix[4]pyridine 23 formed the strongest conjugation system, (NH) 2(NMe)2-bridged calix[4]pyridine 21 acted as a selective fluorescence probe in the recognition of zinc(II) ion in solution with the dramatic enhancement of fluorescence intensity.
- Zhang, En-Xuan,Wang, De-Xian,Huang, Zhi-Tang,Wang, Mei-Xiang
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supporting information; experimental part
p. 8595 - 8603
(2010/03/05)
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- INHIBITORS OF JAK2 KINASE
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Compounds inhibiting the bioactivity of the protein tyrosine kinase JAK2 are provided, along with methods of using the compounds in the treatment of malconditions wherein inhibition of JAK2 is medically indicated. Methods of preparation are also provided
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Page/Page column 27
(2009/03/07)
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- Self-assembly of bidentate ligands for combinatorial homogeneous catalysis based on an A-T base-pair model
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The odd couple: Inspired by the principle of DNA base pairing a conceptually new approach for the generation of a heterobidentate-ligand library based on self-assembly through hydrogen-bonding is realized. From a 4 x 4 library a catalyst that shows outstanding activity and excellent regioselectivity could be identified (see scheme; FGR = functional group, Do = donor group). (Chemical Equation Presented)
- Breit, Bernhard,Seiche, Wolfgang
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p. 1640 - 1643
(2007/10/03)
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- Hydroformylation
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The present invention relates to a process for hydroformylating in the presence of a catalyst comprising at least one complex of a metal of transition group VIII with mono-phosphorus compounds which are capable of dimerizing via noncovalent bonds as ligands, to such catalysts and to their use.
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- 6-phenyl-pyridin-2-ylamine derivatives
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The present invention relates to certain 6-phenyl-pyridin-2-ylamine derivatives that exhibit activity as nitric oxide synthase (NOS) inhibitors, to pharmaceutical compositions containing them and to their use in the treatment and prevention of central nervous system disorders.
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- peri-Substituted Imidazopyridines. A New Reductive Elimination Reaction
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A new reductive elimination reaction of 3,5-disubstituted imidazopyridines (3) with hydrazine is reported.Thus on treatment of the 3,5-dibromo (7a), 5-bromo-3-nitro (7b), and 3,5-dinitro (4) derivatives with hydrazine hydrate in hot ethanol, the bromine and nitro groups are replaced by hydrogen.A mechanism based on the conjugated relationship of these peri-substituents is proposed and used to explain the reported conversion of 1,3,5-trichloro-2,4,6-trinitrobenzene (9) into 1,3-dichloro-4,6-dinitrobenzene (10).A variety of other 3-nitro-5-substituted imidazopyridines (15)-(18) is described, but these could not be cyclised to 1,2,4-triazacyclopentindenes.The 3-amino-5-methoxycarbonyl derivative (19a) cyclises to the triazacyclopentindenone (20) with sodium methoxide.
- Rees, Charles W.,Smith, David I.
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p. 1159 - 1164
(2007/10/02)
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- Substituent Effects on the Isomer Ratios in the Rearrangement of Some 2- and 4-Nitraminopyridines
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The preparation, and rearrangement in 92percent sulfuric acid, of 4-X-2-nitramino- (1), 2-X-4-nitramino- (2), and 6-X-2-nitramino-pyridines (3) is reported (X=H,Me,MeO,Br,Cl,CO2H).The product isomer ratios can be explained by differential electronic stabilization of the appropriate ? complexes for aromatic nitration and steric effects seem relatively unimportant.Deuteration had no effect on the product distribution
- Deady, Leslie W.,Korytsky, Olga L.,Rowe, Jeffrey E.
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p. 2025 - 2034
(2007/10/02)
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