54243-43-5Relevant academic research and scientific papers
BI-ARYL DIHYDROOROTATE DEHYDROGENASE INHIBITORS
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Page/Page column 208, (2021/04/17)
Disclosed are compounds, compositions and methods for treating diseases, disorders, or medical conditions that are affected by the modulation of DHODH. Such compounds are represented by Formula I as follows: Formula I wherein R1, R2, R3, and Q are defined herein.
TBK/IKK INHIBITOR COMPOUNDS AND USES THEREOF
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Paragraph 1162; 1163, (2017/01/23)
The present invention relates to compounds of Formula I and pharmaceutically acceptable compositions thereof, useful as TBK/IKKε inhibitors.
3-azabicyclo[3.1.0]hex-1-ylamines by Ti-mediated intramolecular reductive cyclopropanation of α-(N-allylamino)-substituted N,N-dialkylcarboxamides and carbonitriles
Gensini, Martina,Kozhushkov, Sergei I.,Yufit, Dmitrii S.,Howard, Judith A. K.,Es-Sayed, Mazen,De Meijere, Armin
, p. 2499 - 2507 (2007/10/03)
A variety of tris- and monoprotected derivatives with the 1-amino-3-azabicyclo[3.1.0]hexane and 1-amino-3-azabicy- clo[4.1.0]heptane skeleton 10 have been synthesized by intramolecular reductive cyclopropanation of α-(N-allylamino)-substituted N,N-dialkylcarboxamides 6, 8, and 9. Starting from derivatives of the naturally occurring amino acid serine (4a, 4b), the enantiomerically pure compounds 10a and 10b were obtained with endo/exo ratios of 2.5:1 (a) and 2:1 (b), in 26 and 30% overall yields, respectively. The unprotected bicyclic amines 11aa, 11ab, 11ba, and 11ad have been prepared by palladium-catalyzed hydrogenative deprotection of 10aa, 10ab, 10ba and 10ad, respectively, under acidic conditions, in 91, 95, 96, and 99% yields, respectively. X-ray crystal structure analyses of 10aa and 10ad in each case found an equatorial position of the N-benzyl group on the heterocycle and a common boat conformation for the 3-azabicyclo[3.1.0]hexane and 3-azabicyclo[4.1.0]heptane skeletons as a whole. One-step preparations of the bicyclic diamiries 11ac (41% yield) and 14a (48% yield) have been performed by application of the Kulinkovich-de Meijere procedure to the nitriles 12a and 12b. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Gas Phase Thermolysis of Allyl Cyanomethyl Amine, Diallyl Cyanomethyl Amine, Diethyl Cyanomethyl Amine, and Diethyl Propargyl Amine
Martin, Gonzalo,Ascanio, Julian,Rodriguez, Jesus
, p. 99 - 108 (2007/10/02)
The title amines were pyrolyzed in a stirred-flow reactor at 380 - 510 deg C, pressures of 8 - 15 torr and residence times of 0.3 - 2.4 s, using toluene as carrier gas.The substrates with an allyl group yielded propene and iminonitriles as reaction products.HCN is formed by decomposition of the iminonitriles.The first-order rate coefficients for propene formation fit the Arrhenius equations.Allyl cyanomethyl amine: k(s-1) = 1013.29 +/- 0.35exp(-189 +/- 5 kJ/mol RT) Diallyl cyanomethyl amine: k(s-1) = 1013.00 +/- 0.20exp(-183 +/- 3 kJ/mol RT) Diethyl cyanomethyl amine gave a 20:1 gas mixture of ethylene and ethane, plus HCN.The liquid product fraction contained mainly N-ethyl methanaldimine.The first-order rate coefficients for ethylene formation followed the Arrhenius equation k(s-1) = 1015.30 +/- 0.24exp(-226 +/- 3 kJ/mol RT) Diethyl propargyl amine decomposed cleanly into allene and N-ethyl ethanaldimine.The first-order rate coefficients for allene formation fit the Arrhenius equation k(s-1) = 1012.84 +/- 0.30exp(-168 +/- 4 kJ/mol RT).The results suggest that the above allyl and propargyl amines decompose unimolecularly by mechanisms involving six-center cyclic transition states.For diethyl cyanomethyl amine, a nonchain free radical mechanism is proposed.
SYNTHESE D'IMINES LINEAIRES NON-STABILISEES PAR REACTIONS GAZ-SOLIDE SOUS VIDE(1).
Guillemin, Jean-Claude,Denis, Jean-Marc
, p. 4431 - 4446 (2007/10/02)
Unstabilized imines are synthetized in gram-scale by vacuum dehydrochlorination of N-chloroalkylamines and by vacuum dehydrocyanation of α-aminonitriles on solid base.All the new compounds are characterized at low temperature by 1H, 13C NMR and IR spectroscopy.
