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classificationCPCAdditional http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C2601-08
classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C67-475
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filingDate 2009-12-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 2013-01-27-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber RU-2011130895-A
titleOfInvention METHODS AND INTERMEDIATE COMPOUNDS FOR PRODUCING A MACROCYCLIC INHIBITOR OF HEPATITIS C VIRUS PROTEASE
abstract 1. The method of obtaining compound (VIII), starting from a cichonidine salt (XXa), which undergoes an amide formation reaction with N-methyl-hexenamine (NMHA) (XIX) to give a bicyclic lactone amide (XVIII), in which the lactone group is opened to obtain the desired product (VIII) as shown in the diagram below, wherein R 1 is C 2 alkyl. The method of claim 1, wherein R is methyl. A process according to claim 1 or 2, wherein the amide formation reaction is carried out in the presence of an amide-binding reagent in a reaction inert solvent, optionally in the presence of a base. The method according to claim 3, wherein the solvent contains halogenated hydrocarbons, such as dichloromethane (DCM) or chloroform, ethers, such as tetrahydrofuran (THF) or 2-methyltetrahydrofuran (MeTHF), alcohols, such as methanol or ethanol, hydrocarbon solvents, such as toluene or xylene, dipolar aprotic solvents, such as DMF, DMA, acetonitrile, or mixtures thereof. 5. The method according to claim 3, in which T-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ), N-isopropoxy-carbonyl-2-isopropoxy-1,2-dihydroquinoline (IIDQ) is used as the amide binder of the substance, N , N, N ', N'-tetramethyl-O- (7-azabenzotriazol-1-yl) uronium hexafluorophosphate (HATU), benzotriazol-1-yl-hydroxy-tris-pyrrolidino-phosphonium hexafluorophosphate, CDI, 1-ethyl-3- ( 3-dimethylaminopropyl) carbodiimide (EDCI) or its hydrochloride, dicyclohexylcarbodiimide (DCC), 1,3-diisopropylcarbodiimide, or O-benzotriazole-N, N, N ', N'-tetramethyl-uronium hexafluorophosphate (HBTU), possibly in the presence of a catalyst e.g. an example of 1-hydroxybenzotriazole (HOBt) or 4-dimethylaminopyridine (DMAP) .6. The method of claim 3, wherein tertiary is used as an optional base.
priorityDate 2008-12-23-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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