BR112023022040A2 - Método para a síntese do sal catalisador de carbeno n-heterocíclico da fórmula 1 - Google Patents

Método para a síntese do sal catalisador de carbeno n-heterocíclico da fórmula 1

Info

Publication number
BR112023022040A2
BR112023022040A2 BR112023022040A BR112023022040A BR112023022040A2 BR 112023022040 A2 BR112023022040 A2 BR 112023022040A2 BR 112023022040 A BR112023022040 A BR 112023022040A BR 112023022040 A BR112023022040 A BR 112023022040A BR 112023022040 A2 BR112023022040 A2 BR 112023022040A2
Authority
BR
Brazil
Prior art keywords
synthesis
formula
heterocyclic carbene
catalyst salt
carbene catalyst
Prior art date
Application number
BR112023022040A
Other languages
English (en)
Inventor
Aviad Cahana
A Farone William
Original Assignee
Xf Tech Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Xf Tech Inc filed Critical Xf Tech Inc
Publication of BR112023022040A2 publication Critical patent/BR112023022040A2/pt

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2269—Heterocyclic carbenes
    • B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/009—Preparation by separation, e.g. by filtration, decantation, screening
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/16—Reducing
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/45—Monoamines
    • C07C211/47—Toluidines; Homologues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C241/02—Preparation of hydrazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines
    • C07C243/22—Hydrazines having nitrogen atoms of hydrazine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/20—Diazonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/06—Hydrogenosulfates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

a presente invenção refere-se à síntese dos sais de um catalisador de carbeno n-heterocíclico (nhc) de triazólio em diversas formas de sal preparadas a partir de 2-metilanilina, cloridrato de 2-metilfenil-hidrazina ou 2-metilfenil-hidrazina. as moléculas preparadas dessa forma são úteis na catálise de reações de carbeno e são vantajosas devido à sua carência de intermediários clorados ou fluorados e à carência de cloro ou flúor na estrutura final.
BR112023022040A 2021-04-22 2022-04-16 Método para a síntese do sal catalisador de carbeno n-heterocíclico da fórmula 1 BR112023022040A2 (pt)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202163178381P 2021-04-22 2021-04-22
PCT/US2022/025147 WO2022225825A1 (en) 2021-04-22 2022-04-16 Methods for synthesis of an advantageous n-heterocyclic carbene catalyst

Publications (1)

Publication Number Publication Date
BR112023022040A2 true BR112023022040A2 (pt) 2023-12-26

Family

ID=83722582

Family Applications (1)

Application Number Title Priority Date Filing Date
BR112023022040A BR112023022040A2 (pt) 2021-04-22 2022-04-16 Método para a síntese do sal catalisador de carbeno n-heterocíclico da fórmula 1

Country Status (9)

Country Link
US (1) US20240059701A1 (pt)
EP (1) EP4326702A1 (pt)
JP (1) JP2024515756A (pt)
KR (1) KR20230172524A (pt)
CN (1) CN117529466A (pt)
AU (1) AU2022263339A1 (pt)
BR (1) BR112023022040A2 (pt)
CA (1) CA3216413A1 (pt)
WO (1) WO2022225825A1 (pt)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966900A (en) * 1969-03-12 1976-06-29 Airwick Industries, Inc. Evaporator system comprising a stabilized pesticidal phosphoric acid ester and method for stabilizing such ester enclosed in an evaporator
TW200400963A (en) * 2002-05-21 2004-01-16 Wyeth Corp R-enantiomers of pyranoindole derivatives and the use thereof for the treatment of hepatitis C virus infection or disease
US8501658B2 (en) * 2006-04-21 2013-08-06 The Regents Of The University Of California Enantioselective reactions catalyzed by chiral triazolium salts
JP5747440B2 (ja) * 2009-02-06 2015-07-15 住友化学株式会社 ヒドラジド化合物及びその有害生物防除用途
US8912341B2 (en) * 2013-01-16 2014-12-16 Northwestern University Enantioselective N-heterocyclic carbene-catalyzed annulation reactions with imidazolidinones

Also Published As

Publication number Publication date
CN117529466A (zh) 2024-02-06
US20240059701A1 (en) 2024-02-22
EP4326702A1 (en) 2024-02-28
AU2022263339A1 (en) 2023-11-09
KR20230172524A (ko) 2023-12-22
JP2024515756A (ja) 2024-04-10
CA3216413A1 (en) 2022-10-27
WO2022225825A1 (en) 2022-10-27

Similar Documents

Publication Publication Date Title
Jawiczuk et al. Decomposition of ruthenium olefin metathesis catalyst
Marrero-Ponce Linear indices of the “molecular pseudograph's atom adjacency matrix”: definition, significance-interpretation, and application to QSAR analysis of flavone derivatives as HIV-1 integrase inhibitors
Lu et al. Facile sulfa-Michael reactions with sodium arylsulfinates in water: the promotion of water on the reaction
Lu Structures of multidrug and toxic compound extrusion transporters and their mechanistic implications
Schulte et al. Highly diastereoselective and general synthesis of primary β-fluoroamines
Takahashi et al. Total Synthesis of (−)-Kaitocephalin Based on a Rh-Catalyzed C–H Amination
BR112014010976A2 (pt) composição polimerizável, artigo ótico obtido a partir da mesma e método para a produção de referido artigo ótico
Huang et al. Constructing a quantitative correlation between N-substituent sizes of chiral ligands and enantioselectivities in asymmetric addition reactions of diethylzinc with benzaldehyde
BRPI0519326A2 (pt) derivados de Ácido 2-arilpropiânico e composiÇÕes farmacÊuticas contendo-os
Adamek et al. 1-(N-Acylamino) alkyl Sulfones from N-Acyl-α-amino Acids or N-Alkylamides
Kusaka et al. Role of ring-constrained γ-amino acid residues in α/γ-peptide folding: single-conformation UV and IR spectroscopy
RU2012146732A (ru) Способ получения карбаматного соединения, карбаматное соединение и способ получения изоцианатного соединения с его применением
BR112023022040A2 (pt) Método para a síntese do sal catalisador de carbeno n-heterocíclico da fórmula 1
Bailey et al. Ring-opening and-expansion of 2, 2′-biaziridine: access to diverse enantiopure linear and bicyclic vicinal diamines
Avenoza et al. Stereoselective synthesis of orthogonally protected α-methylnorlanthionine
Nicoletti et al. α, β, γ-Trifluoroalkanes: A stereoselective synthesis placing three vicinal fluorines along a hydrocarbon chain
Pacios et al. Intramolecular effects and relative stabilities of conformers of gaseous glycine
Kruchinin et al. Ion Pairing of the Neurotransmitters Acetylcholine and Glutamate in Aqueous Solutions
Blasius et al. Recognition in Chiral Ionic Liquids: The Achiral Cation Makes the Difference!
Hamilton et al. Bromo-cyclobutenaminones as new covalent UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) inhibitors
Lei et al. A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles
Van Praet et al. One-pot consecutive reductive amination synthesis of pharmaceuticals: from biobased glycolaldehyde to hydroxychloroquine
BRPI0409013A (pt) processos para preparação de um produto de reação, de uma composição farmacêutica, de uma composição agroquìmica, de uma composição de limpeza, de uma composição de tinta e de um refrigerador ou lubrificante
Villavicencio et al. All-hydrocarbon staples and their effect over peptide conformation under different force fields
SG163550A1 (en) Process for the synthesis of sulfonyl halides and sulfonamides from sulfonic acid salts