AR126248A1 - A PROCESS FOR THE PREPARATION OF BICYCLIC ANTHRANYLIC DIAMIDES OF FORMULA (I) AND INTERMEDIATE THEREOF - Google Patents

A PROCESS FOR THE PREPARATION OF BICYCLIC ANTHRANYLIC DIAMIDES OF FORMULA (I) AND INTERMEDIATE THEREOF

Info

Publication number
AR126248A1
AR126248A1 ARP220101674A ARP220101674A AR126248A1 AR 126248 A1 AR126248 A1 AR 126248A1 AR P220101674 A ARP220101674 A AR P220101674A AR P220101674 A ARP220101674 A AR P220101674A AR 126248 A1 AR126248 A1 AR 126248A1
Authority
AR
Argentina
Prior art keywords
formula
salt
compound
group
alkyl
Prior art date
Application number
ARP220101674A
Other languages
Spanish (es)
Inventor
Sanjay Maruti Madurkar
Yuvraj Navanath Kale
Govind Tomar
Dipak Jaysing Dhawade
Pranab Kumar Patra
Alexander Gunther Maria Klausener
Original Assignee
Pi Industries Ltd
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 Pi Industries Ltd filed Critical Pi Industries Ltd
Publication of AR126248A1 publication Critical patent/AR126248A1/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La presente invención proporciona un proceso para la preparación de diamidas antranílicas bicíclicas de la fórmula (I) o de sales de la misma, en donde, R¹, R², Rᵃ, Rᵇ y R³ son como se describen en la descripción. Más particularmente, la presente invención se refiere a un proceso de preparación de diamidas antranílicas bicíclicas de la fórmula (I), que comprende la etapa de preparación de un 2-(5-(2-cianoprop-1-en-1-il)-1H-pirazol-1-il)acetato sustituido de la fórmula (VII) o de sales del mismo haciendo reaccionar un 2-(5-formil-1H pirazol-1-il)acetato sustituido de la fórmula (VIII) o de sales del mismo con un (1-cianoetil)fosfonato sustituido de la fórmula (IX) o de sales del mismo. La invención se refiere además a un proceso de preparación de compuestos intermedios de la fórmula (Z) o de sales del mismo, que son útiles en la preparación del compuesto de la fórmula (I) o de sales del mismo. Reivindicación 1: Un proceso de preparación del producto intermedio de la fórmula (Z) o una sal del mismo, en donde, R se selecciona del grupo que consiste en OR⁶ y NHRᵃRᵇ; R⁶ se selecciona del grupo que consiste en hidrógeno, alquilo C₁-C₄, haloalquilo C₁-C₄ y alquenilo C₂-C₄; Rᵃ y Rᵇ se seleccionan independientemente del grupo que consiste en hidrógeno, alquilo C₁-C₆, alquenilo C₂-C₆, cicloalquilo C₃-C₆, haloalquilo C₁-C₆, halocicloalquilo C₃-C₆ y cicloalquil C₃-C₆-alquilo C₁-C₆; R¹ y R¹ᵃ se seleccionan independientemente del grupo que consiste en hidrógeno, halógeno, alquilo C₁-C₄, haloalquilo C₁-C₄, alquenilo C₂-C₄ y cicloalquilo C₃-C₆; que comprende las etapas de: a) hacer reaccionar un acetonitrilo sustituido (R¹CH₂-CN) de la fórmula (X) con un fosforocloridato de la fórmula (XI) o una sal del mismo, en presencia de una base adecuada, un reactivo adecuado y un disolvente adecuado, para obtener un cianometilfosfonato (sustituido) de la fórmula (IX) o una sal del mismo, en donde, R⁴ y R⁵ se seleccionan cada uno independientemente del grupo que consiste en alquilo C₁-C₄, haloalquilo C₁-C₄ y alquenilo C₂-C₄; o R⁴ y R⁵ junto con el átomo de O al que están unidos pueden formar un anillo de 5 - 8 miembros; y R¹ es como se define en el presente documento anteriormente; b) condensar el compuesto de la fórmula (IX) o una sal del mismo con un compuesto de la fórmula (VIII) o una sal del mismo, en presencia de una base adecuada y un disolvente adecuado para obtener un compuesto de la fórmula (VII) o una sal del mismo, en donde, R⁶ se selecciona del grupo que consiste en alquilo C₁-C₄, haloalquilo C₁-C₄ y alquenilo C₂-C₄; R¹ y R¹ᵃ son como se definen en el presente documento anteriormente; c) ciclar el compuesto de la fórmula (VII) o una sal del mismo en presencia de una base adecuada y un disolvente adecuado para obtener un compuesto de la fórmula (VI) o una sal del mismo, en donde, R¹, R¹ᵃ y R⁶ son como se definen en el presente documento anteriormente; d) hidrolizar el compuesto de la fórmula (VI) o una sal del mismo en presencia de un reactivo hidrolizante adecuado y un disolvente adecuado para obtener un compuesto de la fórmula (V) o una sal del mismo, en donde R¹ y R¹ᵃ son como se definen en el presente documento anteriormente; e) amidar el compuesto de la fórmula (VI) o el compuesto de la fórmula (V) o una sal de los mismos con una amina (NHRᵃRᵇ) de la fórmula (II) para obtener un compuesto de la fórmula (XII) o una sal del mismo, en donde, R¹, R¹ᵃ, Rᵃ y Rᵇ son como se definen en el presente documento anteriormente. Reivindicación 5: Un proceso de preparación de un compuesto de la fórmula (Ia) o una sal del mismo, en donde, R¹ se selecciona del grupo que consiste en metilo, trifluorometilo o halógeno; Rᵃ se selecciona del grupo que consiste en metilo, etilo, n-propilo, iso-propilo, n-, iso- o terc-butilo; y Rᵇ se selecciona del grupo que consiste en hidrógeno o metilo; que comprende las etapas de: a) hacer reaccionar un acetonitrilo (CH₃CH₂-CN) de la fórmula (Xa) con un fosforocloridato de la fórmula (XIa) o una sal del mismo, en presencia de una base adecuada, un reactivo adecuado y un disolvente adecuado, para obtener un cianometilfosfonato (sustituido) de dietilo de la fórmula (IXa) o una sal del mismo, en donde R¹ es como se define en el presente documento anteriormente; b) condensar el compuesto de la fórmula (IXa) o una sal del mismo con un compuesto de la fórmula (VIIIa) o una sal del mismo, en presencia de una base adecuada y un disolvente adecuado, para obtener un compuesto de la fórmula (VIIa) o una sal del mismo, en donde R¹ es como se define en el presente documento anteriormente; c) ciclar el compuesto de la fórmula (VIIa) o una sal del mismo en presencia de una base adecuada y un disolvente adecuado, para obtener un compuesto de la fórmula (VIa) o una sal del mismo, en donde R¹ es como se define en el presente documento anteriormente; d) hidrolizar el compuesto de la fórmula (VIa) o una sal del mismo en presencia de un reactivo hidrolizante adecuado y un disolvente adecuado, para obtener un compuesto de la fórmula (Va) o una sal del mismo, en donde R¹ es como se define en el presente documento anteriormente; opcionalmente, e) amidar el compuesto de la fórmula (VIa) o el compuesto de la fórmula (Va) o una sal de los mismos con una amina adecuada [(CH₃)₂CH-NH₂] de la fórmula (IIa), para obtener un compuesto de la fórmula (XIIa) o una sal del mismo, en donde R¹, Rᵃ y Rᵇ son como se definen en el presente documento anteriormente; f) acoplar el compuesto de la fórmula (Va) o una sal del mismo con un compuesto de la fórmula (IVa) o una sal del mismo, en presencia de un reactivo de acoplamiento adecuado, una base adecuada y un disolvente adecuado, para obtener un compuesto de la fórmula (IIIa) o una sal del mismo, en donde R¹ es como se define en el presente documento anteriormente; y g) amidar el compuesto de la fórmula (IIIa) o una sal del mismo con una amina adecuada [(CH₃)₂CH-NH₂] de la fórmula (IIa), para obtener un compuesto de la fórmula (Ia) o una sal del mismo, en donde R¹, Rᵃ y Rᵇ son como se definen en el presente documento anteriormente; opcionalmente, h) acoplar el compuesto de la fórmula (XIIa) o una sal del mismo, con un compuesto de la fórmula (IVa) o una sal del mismo, en presencia de un reactivo adecuado, una base adecuada y un disolvente adecuado, para obtener un compuesto de la fórmula (Ia) o una sal del mismo, en donde R¹, Rᵃ y Rᵇ son como se definen en el presente documento anteriormente. Reivindicación 12: Un compuesto de la fórmula (IIIA) en donde, R¹ y R¹ᵃ se seleccionan independientemente del grupo que consiste en hidrógeno, halógeno, alquilo C₁-C₄, haloalquilo C₁-C₄, alquenilo C₂-C₄ y cicloalquilo C₃-C₆; R² se selecciona del grupo que consiste en halógeno, CHF₂, CF₃, OCF₂H, OCH₂CF₃, y; en donde A representa CRᶜRᶜ, NRᶜ, O o S(O)₀₋₂; Rᶜ se selecciona del grupo que consiste en hidrógeno y alquilo C₁-C₄; R³ se selecciona del grupo que consiste en hidrógeno, halógeno, alquilo C₁-C₄ y haloalquilo C₁-C₄; R⁶ se selecciona del grupo que consiste en hidrógeno y alquilo C₁-C₄; n es un número entero, seleccionado desde 1 hasta 3.The present invention provides a process for the preparation of bicyclic anthranilic diamides of formula (I) or salts thereof, wherein, R¹, R², Rᵃ, Rᵇ and R³ are as described in the description. More particularly, the present invention relates to a process for preparing bicyclic anthranilic diamides of the formula (I), which comprises the step of preparing a 2-(5-(2-cyanoprop-1-en-1-yl) -Substituted 1H-pyrazol-1-yl)acetate of formula (VII) or salts thereof by reacting a substituted 2-(5-formyl-1H pyrazol-1-yl)acetate of formula (VIII) or salts thereof with a substituted (1-cyanoethyl)phosphonate of the formula (IX) or salts thereof. The invention further relates to a process for preparing intermediate compounds of formula (Z) or salts thereof, which are useful in the preparation of the compound of formula (I) or salts thereof. Claim 1: A process of preparing the intermediate product of formula (Z) or a salt thereof, wherein, R is selected from the group consisting of OR⁶ and NHRᵃRᵇ; R⁶ is selected from the group consisting of hydrogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl and C₂-C₄ alkenyl; Rᵃ and Rᵇ are independently selected from the group consisting of hydrogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₃-C₆ halocycloalkyl and C₃-C₆ cycloalkyl-C₁-C₆ alkyl; R¹ and R¹ᵃ are independently selected from the group consisting of hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl and C₃-C₆ cycloalkyl; comprising the steps of: a) reacting a substituted acetonitrile (R¹CH₂-CN) of the formula (X) with a phosphorochloridate of the formula (XI) or a salt thereof, in the presence of a suitable base, a suitable reagent and a suitable solvent, to obtain a (substituted) cyanomethylphosphonate of the formula (IX) or a salt thereof, wherein, R⁴ and R⁵ are each independently selected from the group consisting of C₁-C₄ alkyl, C₁-C₄ haloalkyl and alkenyl C₂-C₄; or R⁴ and R⁵ together with the O atom to which they are attached can form a 5-8 membered ring; and R¹ is as defined herein above; b) condense the compound of the formula (IX) or a salt thereof with a compound of the formula (VIII) or a salt thereof, in the presence of a suitable base and a suitable solvent to obtain a compound of the formula (VII ) or a salt thereof, wherein, R⁶ is selected from the group consisting of C₁-C₄ alkyl, C₁-C₄ haloalkyl and C₂-C₄ alkenyl; R¹ and R¹ᵃ are as defined herein above; c) cyclizing the compound of the formula (VII) or a salt thereof in the presence of a suitable base and a suitable solvent to obtain a compound of the formula (VI) or a salt thereof, where, R¹, R¹ᵃ and R⁶ are as defined herein above; d) hydrolyzing the compound of the formula (VI) or a salt thereof in the presence of a suitable hydrolyzing reagent and a suitable solvent to obtain a compound of the formula (V) or a salt thereof, where R¹ and R¹ᵃ are as are defined herein above; e) amidate the compound of the formula (VI) or the compound of the formula (V) or a salt thereof with an amine (NHRᵃRᵇ) of the formula (II) to obtain a compound of the formula (XII) or a salt thereof, wherein, R¹, R¹ᵃ, Rᵃ and Rᵇ are as defined herein above. Claim 5: A process of preparing a compound of formula (Ia) or a salt thereof, wherein, R¹ is selected from the group consisting of methyl, trifluoromethyl or halogen; Rᵃ is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-, iso- or tert-butyl; and Rᵇ is selected from the group consisting of hydrogen or methyl; comprising the steps of: a) reacting an acetonitrile (CH₃CH₂-CN) of the formula (Xa) with a phosphorochloridate of the formula (XIa) or a salt thereof, in the presence of a suitable base, a suitable reagent and a suitable solvent, to obtain a (substituted) diethyl cyanomethylphosphonate of the formula (IXa) or a salt thereof, wherein R¹ is as defined herein above; b) condense the compound of the formula (IXa) or a salt thereof with a compound of the formula (VIIIa) or a salt thereof, in the presence of a suitable base and a suitable solvent, to obtain a compound of the formula ( VIIa) or a salt thereof, where R¹ is as defined herein above; c) cyclizing the compound of the formula (VIIa) or a salt thereof in the presence of a suitable base and a suitable solvent, to obtain a compound of the formula (VIa) or a salt thereof, where R¹ is as defined herein above; d) hydrolyzing the compound of the formula (VIa) or a salt thereof in the presence of a suitable hydrolyzing reagent and a suitable solvent, to obtain a compound of the formula (Va) or a salt thereof, where R¹ is as defined herein above; optionally, e) amidate the compound of the formula (VIa) or the compound of the formula (Va) or a salt thereof with a suitable amine [(CH₃)₂CH-NH₂] of the formula (IIa), to obtain a compound of the formula (XIIa) or a salt thereof, wherein R¹, Rᵃ and Rᵇ are as defined herein above; f) coupling the compound of the formula (Va) or a salt thereof with a compound of the formula (IVa) or a salt thereof, in the presence of a suitable coupling reagent, a suitable base and a suitable solvent, to obtain a compound of formula (IIIa) or a salt thereof, wherein R¹ is as defined herein above; and g) amidate the compound of the formula (IIIa) or a salt thereof with a suitable amine [(CH₃)₂CH-NH₂] of the formula (IIa), to obtain a compound of the formula (Ia) or a salt thereof , where R¹, Rᵃ and Rᵇ are as defined herein above; optionally, h) coupling the compound of the formula (XIIa) or a salt thereof, with a compound of the formula (IVa) or a salt thereof, in the presence of a suitable reagent, a suitable base and a suitable solvent, to obtain a compound of the formula (Ia) or a salt thereof, wherein R¹, Rᵃ and Rᵇ are as defined herein above. Claim 12: A compound of the formula (IIIA) wherein, R¹ and R¹ᵃ are independently selected from the group consisting of hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl and C₃-C₆ cycloalkyl; R² is selected from the group consisting of halogen, CHF₂, CF₃, OCF₂H, OCH₂CF₃, and; where A represents CRᶜRᶜ, NRᶜ, O or S(O)₀₋₂; Rᶜ is selected from the group consisting of hydrogen and C₁-C₄ alkyl; R³ is selected from the group consisting of hydrogen, halogen, C₁-C₄ alkyl and C₁-C₄ haloalkyl; R⁶ is selected from the group consisting of hydrogen and C₁-C₄ alkyl; n is an integer, selected from 1 to 3.

ARP220101674A 2021-06-28 2022-06-27 A PROCESS FOR THE PREPARATION OF BICYCLIC ANTHRANYLIC DIAMIDES OF FORMULA (I) AND INTERMEDIATE THEREOF AR126248A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IN202111028885 2021-06-28

Publications (1)

Publication Number Publication Date
AR126248A1 true AR126248A1 (en) 2023-10-04

Family

ID=82703044

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP220101674A AR126248A1 (en) 2021-06-28 2022-06-27 A PROCESS FOR THE PREPARATION OF BICYCLIC ANTHRANYLIC DIAMIDES OF FORMULA (I) AND INTERMEDIATE THEREOF

Country Status (4)

Country Link
AR (1) AR126248A1 (en)
TW (1) TW202317562A (en)
UY (1) UY39833A (en)
WO (1) WO2023275705A1 (en)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3728256B1 (en) 2017-12-20 2024-10-02 PI Industries Ltd. Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same
EP3927685A4 (en) * 2019-02-22 2022-11-23 PI Industries Ltd. A process for the synthesis anthranilic diamide compounds and intermediates thereof
WO2021010492A1 (en) * 2019-07-17 2021-01-21 Ono Pharmaceutical Co., Ltd. Compound having kdm5 inhibitory activity and pharmaceutical use thereof
AR123052A1 (en) * 2020-07-27 2022-10-26 Pi Industries Ltd A PESTICIDALLY ACTIVE MIXTURE COMPRISING THE PYRAZOLOPYRIDINE COMPOUND ANTHRANILAMIDE, ITS OXIDES OR SALTS THEREOF

Also Published As

Publication number Publication date
UY39833A (en) 2023-01-31
WO2023275705A1 (en) 2023-01-05
TW202317562A (en) 2023-05-01

Similar Documents

Publication Publication Date Title
HRP20191303T1 (en) Pyrrolo [1,2,f][1,2,4]triazines useful for treating respiratory syncitial virus infections
EA200701076A1 (en) ANTRANYLAMIDE INSECTICIDES
CY1117428T1 (en) PHARMACEUTICAL UNIONS
RU2009124304A (en) Derivatives of azabicyclooctane, a method for their production and their use as inhibitors of dipeptidyl peptidase IV
RU2012104214A (en) ANTIVIRAL COMPOUNDS AND METHODS FOR PRODUCING AND USING THEM
ECSP045317A (en) PYRIDINOILPIPERIDINS AS AGONISTS OF 5-HT1F
AR029717A1 (en) DERIVATIVES OF THE PRO-PHARMACO OF 4-PHENYL-PYRIDINE
MA22252A1 (en) NOVEL 4-BENZYLISOXAZOLE DERIVATIVES, PROCESS FOR PRODUCING THE SAME, AND HERBICIDE COMPOSITION CONTAINING THEM
ECSP034475A (en) DERIVATIVES OF 4-PHENYL-PIRIDIN AS ANTAGONISTS OF THE NEUROQUININE RECEIVER-1
TW200301678A (en) α -Cyanoacrylates
AR087915A1 (en) N- (3- (2-AMINO-6,6-DIFLUOR-4,4A, 5,6,7,7A-HEXAHYDRO-CYCLOPENTA- [E] [1,3] OXAZIN-4-IL) -PENYL) - AMIDAS AS INHIBITORS OF THE BACE1
AR058779A1 (en) DERIVATIVES OF TIAZOL AND OXAZOL AS INHIBITORS OF PTP-1B, PHARMACEUTICAL COMPOSITIONS
AR075367A1 (en) GLUCOSILCERAMIDE SINTASA INHIBITORS
MX2019007721A (en) Fused heterocyclic compound having oxime group or salts thereof, agricultural/horticultural insecticide containing said compounds, and method for using said insecticide.
AR124008A1 (en) BICYCLIC 1,4-DIAZEPANONES AND ITS THERAPEUTIC USES
CL2022000904A1 (en) Process for the preparation of compounds represented by formulas iv, vii and ia; and a polymorph of the compound of formula ia (div. sol. 202001814).
AR127801A1 (en) PYRAZOLE-PYRIMIDINE HERBICIDAL COMPOUNDS
AR042002A1 (en) SUBSTITUTED BENZOXAZINONAS, OBTAINING PROCESS AND USES FOR TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES.
AR119790A1 (en) ISOXAZOLINE COMPOUNDS AND THEIR USE AS PEST CONTROL AGENTS
AR126248A1 (en) A PROCESS FOR THE PREPARATION OF BICYCLIC ANTHRANYLIC DIAMIDES OF FORMULA (I) AND INTERMEDIATE THEREOF
JP2021514984A (en) 10- (di (phenyl) methyl) -4-hydroxy-8,9,9a, 10-tetrahydro-7H-pyrrolo [1', 2': 4 as an inhibitor of orthomyxovirus replication to treat influenza , 5] Pyrazino [1,2-b] pyridazine-3,5-dione derivatives and related compounds
AR069030A1 (en) DERIVATIVES OF 1,2,4-TRIAZOL AMINO AND ISOXAZOLES, PHARMACEUTICAL COMPOSITIONS THAT INCLUDE THEM AND USES OF THE SAME IN THE TREATMENT OF GASTROINTESTINAL DISORDERS AND SNC
JP2690816B2 (en) Quinolinyl oxadiazole herbicide
ES2601849T3 (en) Phosphonate syntheses for the synthesis of phosphonate derivatives that show better bioavailability
AR126733A1 (en) NICOTINAMIDE RIPK1 INHIBITORS

Legal Events

Date Code Title Description
FB Suspension of granting procedure