http://rdf.ncbi.nlm.nih.gov/pubchem/patent/NZ-700642-A
Outgoing Links
Predicate | Object |
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assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_b09f893b262cefd50c5e76c4b85d1c0a |
classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D233-58 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D233-56 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61K31-4164 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D263-16 |
classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D233-56 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-4164 |
filingDate | 2012-11-15-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_95d34b75a0fb3a0bd83a28d1350937fb http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_550f4dc60023c41acdb58f6d50801176 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_9a7435fce459fac10585fc1cd7c342f1 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_93524ce33f89a7859f07ca354f433389 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_55ceb44dbafd3cb4cd71a2faf22821d4 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_473d53307949e338a07ea61b17817b7b |
publicationDate | 2016-04-29-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationNumber | NZ-700642-A |
titleOfInvention | Method for preparation of medetomidine with chloroacetone |
abstract | The technical problem of the invention relates to a method for the preparation of medetomidine starting from 1-bromo-2,3-dimethylbenzene and chloroacetone. Medetomidine is the compound of formula (XX) and is an alpha2 adrenergic agonist, which is currently being used as a veterinary sedative and analgesic and is evaluated as anesthetic. The solution to the problem involves a method for the preparation of a compound of formula (XX); the method comprises four steps, the four steps are a step (Q1), a step (Q2), a step (N) and a step (M1); compound of formula (XX) is prepared in step (M1); step (M1) comprises a reaction (M1-reac); reaction (M1-reac) is a reaction between a compound of formula (XXI); a reagent (M-reag) and a reagent (M-A) in a solvent (M-solv); reagent (M-reag) is selected from the group consisting of p-toluenesulfonylmethyl isocyanide, trifluoromethanesulfonylmethyl isocyanide, methanesulfonylmethyl isocyanide, benzenesulfonylmethyl isocyanide, and 4-acetamidobenzenesulfonylmethyl isocyanide, or mixtures thereof; reagent (M-A) is selected from the group consisting of ammonia, sulfamic acid, p-toluenesulfonamide, benzenesulfonamide, 4-acetamidobenzenesulfonamide, tritylamine, formamide, urea, urotropine, ethyl carbamate, and acetamide, or mixtures thereof; solvent (M-solv) is selected from the group consisting of N,N-dimethylformamide, C1-6 alkanol, formamide, 1,2-dimethoxyethane, NMP, toluene, acetonitrile, propionitrile, ethyl carbamate, N,N-dimethylacetamide, water, and acetamide, or mixtures thereof; compound of formula (XXI) is prepared in step (N); step (N) comprises a reaction (N-reac); reaction (N-reac) is a reaction of a compound of formula (XXII) with a catalyst (N-cat); catalyst (N-cat) is selected from the group consisting of acetic acid, formic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, camphorsulfonic acid, HCl, HBr, H2SO4, HNO3, H3PO4, HClO4, BCl3, BBr3, BF3OEt2, BF3SMe2, BF3THF, MgCl2, MgBr2, MgI2, AlCl3, Al(O-C1-4 alkyl)3, SnCl4, TiCl4, Ti(O-C1-4 alkyl)4, ZrCl4, Bi2O3, BiCl3, ZnCl2, PbCl2, FeCl3, ScCl3, NiCl2, Yb(OTf)3, Yb(Cl)3, GaCl3, AlBr3, Ce(OTf)3, LiCl, Cu(BF4)2, Cu(OTf)2, NiBr2(PPh3)2, NiBr2, NiCl2, Pd(OAc)2, PdCl2, PtCl2, InCl3, acidic inorganic solid substance, acidic ion exchange resin, and carbon treated with inorganic acid, or mixtures thereof; step (Q1) comprises a reaction (Q1-reac); reaction (Q1-reac) is a reaction of a compound of formula (XXV) with a reagent (Q1-reag) to provide a reaction product of reaction (Q1-reac); R1 is Br, Cl, or I; reagent (Q1-reag) is selected from the group consisting of lithium, magnesium, aluminum, zinc, calcium, propylmagnesium chloride, propylmagnesium bromide, and butyllithium, or mixtures thereof; step (Q2) comprises a reaction (Q2-reac); reaction (Q2-reac) is a reaction of the reaction product of reaction (Q1-reac) with chloroacetone; compound of formula (XXII) is prepared by the reaction (Q2-reac). |
priorityDate | 2012-06-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
type | http://data.epo.org/linked-data/def/patent/Publication |
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