DESC:FORM 2

THE PATENT ACT, 1970
(39 of 1970)

COMPLETE SPECIFICATION
(See section 10, rule 13)

“AN IMPROVED PROCESS FOR PREPARATION OF 2-AMINO-5-CHLORO-N-3-DIMETHYL BENZAMIDE”

Laurus Labs Limited, an Indian company of DS-1, IKP Knowledge Park, Genome Valley, Turkapally, Shameerpet Mandal, Medchal-Malkajgiri district, Hyderabad-500 078, Telangana, INDIA

THE FOLLOWING SPECIFICATION PARTICULARLY DESCRIBES THE INVENTION AND THE MANNER IN WHICH IT IS TO BE PERFORMED.

FIELD OF THE INVENTION

The present invention relates to an improved process for preparation of 2-amino-5-chloro-N-3-dimethylbenzamide of Formula IV, an intermediate for preparation of chlorantraniliprole or a salt thereof.

BACKGROUND OF THE INVENTION

Chlorantraniliprole is a class of anthranilic-diamide insecticide derivative compounds and is chemically known as 3-Bromo-N-[4-chloro-2-methyl-6-(methyl carbamoyl) phenyl]-1-(3-chloro-2-pyridine-2-yl)-1H-pyrazole-5-carboxamide, it has the following structure:

Chlorantraniliprole

Chlorantraniliprole is being developed world-wide by DuPont belonging to a new class of selective insecticides featuring a novel mode of action to control a range of pests belonging to the order Lepidoptera and some other Coleoptera, Diptera and Isoptera species.

PCT application Number: 2008/010897 (“the ‘897 publication”) discloses a process for preparation of compound of Formula IV, as follows:

Chinese application Number: 103539694 (“the ‘694 publication”) discloses a process for preparation of compound of Formula IV, as follows:

The ‘897 and ‘694 applications disclosed preparation of compound of Formula IV in three stage process from either 2-amino-3-methyl benzoic acid/ester of Formula I and the process involves isolation of intermediate products of Formula II and Formula III as solid, which makes the process lengthy as it involves multiple steps of solvent extractions, isolation and drying steps and this leads to low yield of the Formula IV from the starting compound of Formula I.

Further other known literatures for ex:WO2006/062978, CN111134128A, CN103109816B, CN112457209Aand CN103694219A discloses preparation of this compound of Formula IV but all the literatures involves the same processing strategies,isolation of intermediates as mentioned under the ‘897 and ‘978 publications.

Chlorantraniliprole is one of the important insecticide available in the market. As all the reported processes involves isolation of each intermediate products of Formula II and Formula III as solid in the preparation of Formula IV, which involves increasing the reactor occupancyand additional process steps such as use of multiple solvent systems for each stage, isolation of each stage by filtration, drying and testing of each intermediate; hence, the reported processes requires excessreactor occupancy and excess manufacturing time and this creates extra burden to the final cost of the material.The compound of Formula IV is the key cost contributor in the preparation of chlorantraniliprole and to reduce the manufacturing cost of the chlorantraniliprole it is desirable to reduce the manufacturing cost of the intermediates involved in the process.

Hence, it’s important to develop a simple and cost effective improved process for preparation of pure chlorantraniliprole or its intermediates with high yield, which is readily amenable to large scale production and free from its impurities.

The main object of the present invention is to provide a simple, cost effective,high yield process for the preparation of compound of Formula IV with avoiding the aforementioned problems. Further, the present invention relates to conversion of the compound of Formula IV to chlorantraniliprole or a salt thereof.

SUMMARY OF THE INVENTION

Accordingly, the present invention provides an improved process for preparation of compound of Formula IV. Further, the present invention providesan improved process for preparation of compound of chlorantraniliprole through preparing the compound of Formula IV.

In accordance with one embodiment, the present invention provides an improved process for preparation of compound of Formula IV, comprising:

Formula IV
a) reacting a compound of Formula I with a source of chloride in a suitable solvent to obtain a compound of Formula II,

Formula I Formula II
b) reacting the compound of Formula II with phosgene or its derivative and a suitable baseto obtain a compound of Formula III, and

Formula III
c) reacting the compound of Formula III with a source of monomethyl amine to obtain a compound of Formula IV.

In accordance with another embodiment, the present invention provides an improved process for preparation of compound of Formula IV, comprising:
a) reacting a compound of Formula I with a source of chloride in a suitable solvent to obtain a compound of Formula II,
b) reacting the compound of Formula II with phosgene or its derivative and a suitable baseto obtain a compound of Formula III, and
c) reacting the compound of Formula III with a source of monomethyl amine to obtain a compound of Formula IV; wherein the steps a) to c) are carried out in one-pot reaction.

In accordance with another embodiment, the present invention provides an improved process for preparation of compound of Formula IV, comprising:
a) reacting a compound of Formula I with a source of chloride in a suitable solvent to obtain a compound of Formula II,
b) reacting the compound of Formula II with phosgene or its derivative and a suitable baseto obtain a compound of Formula III, and
c) reacting the compound of Formula III with a source of monomethyl amine to obtain a compound of Formula IV; wherein the steps b) and c) are carried out in one-pot reaction.

In accordance with another embodiment, the present invention provides an improved process for preparation of compound of Formula IV, comprising:
a) reacting a compound of Formula I with a source of chloride in a suitable solvent to obtain a compound of Formula II,
b) reacting the compound of Formula II with phosgene or its derivative and a suitable base to obtain a compound of Formula III,
c) reacting the compound of Formula III with a source of monomethyl amine to obtain a compound of Formula IV,
d) adding water to the step c) reaction mass,
e) optionally, concentrating the solution at below 50°C,
f) optionally, adding an organic solvent to the step e) reaction mass, and
g) filtering the compound of Formula IV.

In accordance with another embodiment, the present invention provides an improved process for preparation of compound of Formula IV, comprising:
a) reacting a compound of Formula I with a source of chloride in a suitable solvent to obtain a compound of Formula II,
b) adding water and a suitable base to the step a) reaction mass,
c) optionally, concentrating the solution at below 50°C,
d) filtering the compound of Formula II,
e) reacting the compound of Formula II with phosgene or its derivative and a suitable base to obtain a compound of Formula III, and
f) reacting the compound of Formula III with a source of monomethyl amine to obtain a compound of Formula IV.

In accordance with another embodiment, the present invention provides an improved process for preparation of compound of Formula IV, comprising:
a) reacting a compound of Formula I with a source of chloride in a suitable solvent to obtain a compound of Formula II,
b) adding water and a suitable base to the step a) reaction mass,
c) optionally, concentrating the solution at below 50°C,
d) filtering the compound of Formula II,
e) reacting the compound of Formula II with phosgene or its derivative and a suitable base in a suitable solvent to obtain a reaction solution of compound of Formula III,
f) reactingthesolution of compound of Formula III of step e) with a source of monomethyl amine,
g) adding water to the step f) reaction mass,
h) optionally, concentrating the solution at below 50°C,
i) optionally, adding an organic solvent to the step h) reaction mass, and
j) isolating the compound of Formula IV.

In accordance with another embodiment, the present invention provides an improved process for preparation of chlorantraniliprole, comprising:

Chlorantraniliprole

a) preparing a compound of Formula IV according to processes described as above, and
b) converting the compound of Formula IV in to chlorantraniliprole.

In accordance with another embodiment, the present invention provides a composition comprising chlorantraniliprole, prepared by the process of the present invention and/or at least one excipient.

DETAILED DESCRIPTION OF THE INVENTION

The present invention encompasses an improved process for the preparation of compound of Formula IV with high product yield and quality, wherein the improvements involve use of one-pot process without isolating intermediate compounds in a single solvent system and avoids multiple solvent systems andcumbersome isolations such as time consuming solvent workups, drying and necessity of analyzing the compounds at each stage.

In accordance with one embodiment, the present invention provides an improved process for preparation of compound of Formula IV, comprising:

Formula IV
a) reacting a compound of Formula I with a source of chloride in a suitable solvent to obtain a compound of Formula II,

Formula I Formula II
b) reacting the compound of Formula II with phosgene or its derivative and a suitable base to obtain a compound of Formula III, and

Formula III
c) reacting the compound of Formula III with a source of monomethyl amine to obtain a compound of Formula IV.

In a preferred embodiment, the present invention provides an improved process for preparation of compound of Formula IV, wherein the steps a) to c) are carried out in one-pot reaction and without isolating the intermediates II and III as solid.

In another preferred embodiment, the present invention provides an improved process for preparation of compound of Formula IV, wherein the steps b) and c) are carried out in one-pot reaction and without isolating the intermediate III as solid.

The term "one-pot" as used in this application means a process uses a strategy to improve the efficiency of a chemical reaction whereby a reactant is subjected to successive chemical reactions in just one solvent/reactor. This is much desired by chemists because avoiding a lengthy separation process and purification of the intermediate chemical compounds can save time and resources, improves the efficiency of a chemical reaction, and offers better chemical yield.

The source of chloride used in aforementioned step a) is selected from the group consisting of but not limited to sulfuryl chloride, N-chlorosuccinimide, chlorine gas, metal chloride-H2O2 in acid aqueous medium, HCl-H2O2, m-chloroperbenzoic acid/HCl, acetyl chloride and the like; preferably Sulfuryl chloride or N-Chlorosuccinimide; more preferably Sulfuryl chloride.

The suitable solvent used in aforementioned step a) is selected from the group consisting of but not limited to amides, esters, ketones, nitriles, ethers, halogenated hydrocarbons, aromatic hydrocarbons and the like and mixtures thereof. The amides include, but are not limited to dimethylacetamide, dimethylformamide, N-methylpyrrolidone and the like and mixtures thereof; esters include, but are not limited to ethyl acetate, methyl acetate and the like and mixtures thereof; ketones include, but are not limited to acetone, methyl isobutyl ketone, methyl ethyl ketone and the like and mixtures thereof; nitriles include, but are not limited to acetonitrile, propionitrile and the like and mixtures thereof; ethers include, but are not limited to tetrahydrofuran, methyl tetrahydrofuran, dimethyl ether, diisopropyl ether, methyl tertiary butyl ether, 1,4-dioxane and the like and mixtures thereof; halogenated hydrocarbons include, but are not limited to methylene chloride, ethylene chloride, chloroform and the like and mixtures thereof; aromatic hydrocarbons include, but are not limited to toluene, xylene and the like and mixture thereof; preferably ethyl acetate, acetonitrile or methylene chloride; more preferably methylene chloride.

The reaction of a Formula I with a source of source of chloride is carried out at a temperature of about 25°C to reflux temperature; preferably at about 30°C to about 45°C.

After completion of the step a) reaction, the step a) solution advantageously processed to next step by adding a phosgene or its derivative and a suitable base in a suitable solvent to the step a) solution without isolating the compound of Formula II as solid. Alternatively the resultant compound of formula II may be isolated as a solid by conventional techniques and processed for further stages.

In another embodiment, after completion of the step a) reaction the resultant compound of formula II may be isolated as a solid by adding water to the reaction mass and followed by adjusting pH of the reaction mass to above 7 with a suitable base,optionally concentrating the reaction mass under vacuum at below 50°C. Then the compound of Formula II can be isolated from reaction mass by conventional techniques such as solvent extraction, solvent precipitation, crystallization, concentrated by subjecting the solution to heating, decantation or filtration; preferably by filtering the solids.

The phosgene or its derivative as used in the aforementioned step b) is selected from phosgene as in gaseous form or as in liquid form consisting of but not limited tophosgene, diphosgene, triphosgene, bromophosgeneand the like; preferably triphosgene.

The suitable base used in aforementioned step b) is selected from the group consisting of but not limited to inorganic bases selected from alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide and the like; alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate and the like; alkali metal bicarbonates such as sodium bicarbonate, potassium bicarbonate and the like; organic bases selected from the group comprising of triethylamine, isopropyl ethylamine, diisopropyl amine, diisopropyl ethylamine, N-methyl morpholine, piperidine, 2-picoline, 3-picoline and the like and mixtures thereof; preferably an inorganic base such as sodium carbonate, sodium bicarbonate or potassium bicarbonate; more preferably sodium bicarbonate.

Optionally the step b) is carried out in presence of a suitable second solvent. The suitable second solvent used in aforementioned step b) is selected from the group consisting of but not limited to amides, esters, ketones, nitriles, ethers, halogenated hydrocarbons, aromatic hydrocarbons and the like and mixtures thereof. The amides include, but are not limited to dimethylacetamide, dimethylformamide, N-methylpyrrolidone and the like and mixtures thereof; esters include, but are not limited to ethyl acetate, methyl acetate and the like and mixtures thereof; ketones include, but are not limited to acetone, methyl isobutyl ketone, methyl ethyl ketone and the like; nitriles include, but are not limited to acetonitrile, propionitrile and the like; ethers include, but are not limited to tetrahydrofuran, methyl tetrahydrofuran, dimethyl ether, diisopropyl ether, methyl tertiary butyl ether, 1,4-dioxane and the like; halogenated hydrocarbons include, but are not limited to methylene chloride, ethylene chloride, chloroform and the like; aromatic hydrocarbons include, but are not limited to toluene, xylene and the like and mixture thereof.The suitable second solvent used in aforementioned step b) is same as the solvent used in step a) of the aforesaid process; preferably ethyl acetate, acetonitrile or methylene chloride; more preferably methylene chloride.

The reaction of Formula II with phosgene or its derivative is carried out at a temperature of about 0°C to reflux temperature; preferably at about 20°C to about 40°C.

After completion of the step b) reaction, the step b) solution advantageously processed to next step by adding a source of monomethylamine to the step b) solution without isolating the compound of Formula III as a solid.

The source of monomethylamine used in aforementioned step c) is selected from the group consisting of aqueous methyl amine, methyl amine in solvent, methyl amine gas and the like; preferably aqueous methyl amine or methyl amine gas.

Optionally the step c) is carried out in presence of a suitable acid ora suitable base. The suitable acid optionally used in aforementioned step c) is selected from the group consisting of acetic acid, formic acid, methanoic acid and the like.The suitable base optionally used in aforementioned step c) is selected from the group consisting of but not limited to inorganic bases selected from alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide and the like; alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate and the like; alkali metal bicarbonates such as sodium bicarbonate, potassium bicarbonate and the like; organic bases selected from the group comprising of triethylamine, isopropyl ethylamine, diisopropyl amine, diisopropyl ethylamine, N-methyl morpholine, piperidine, pyridine, 2-picoline, 3-picoline and the like and mixtures thereof.

The reaction of a Formula III with a source of monomethylamine is carried out at a temperature of about 25°C to reflux temperature; preferably at about 30°C to about 45°C.

After completion of the step c) reaction, optionally water may be added to the reaction mass and optionally concentrating the reaction mass under vacuum at below 50°C, then the compound of Formula IV can be isolated from reaction mass by conventional techniques such as solvent extraction, solvent precipitation, crystallization, concentrated by subjecting the solution to heating, decantation or filtration.

In another embodiment, the present invention provides an improved process for the preparation of chlorantraniliprole or a salt thereof, comprising preparing the compound of Formula IV as process described above, and converting the compound of Formula IV in to chlorantraniliprole or a salt thereof by any process known in the art for example WO2006/062978 or by the process described in the present specification.

In another embodiment, the present invention provides a composition comprising chlorantraniliprole, prepared by the process of the present invention and/or at least one excipient.

The present invention provides chlorantraniliprole and its intermediates, obtained by the above process, as analyzed using high performance liquid chromatography (“HPLC”) with the conditions are tabulated below:

Column Zorbax RX-C8
Mobile phase Mobile phase-A: Buffer and Acetonitrile
Mobile phase-B: Acetonitrile and water
Flow rate 1.0 mL/min
Elution Gradient
Detection 250 nm
Injection volume 20µL
Run time 75 min
Mode Time (min) Mobile phase-A
(% v/v) Mobile phase-B
(% v/v)
0 80 20
40 55 45
65 20 80
70 80 20

EXAMPLES

The following non-limiting examples illustrate specific embodiments of the present invention. They are not intended to be limiting the scope of the present invention in any way.

EXAMPLE-1:

Preparation of compound of Formula II

Compound of Formula I (100 gm) and methylene chloride (800 mL) were added in to a round bottom flask and stir for 10-20 min at 25-35°C. To the reaction mass was added Sulfuryl chloride (142.9 gm) was added slowly at 25-35°C and stir for 6 hrs at same temperature. After completion of the reaction, to the reaction mass was added water (700 mL) at same temperature. pH of the reaction mass was adjusted to 6-7 with aq sodium hydroxide solution at 10°C to 15°C. The reaction mass was concentrated under vacuum at 45-55°C. Then the reaction mass was allowed to cool to 25-35°C, filtered and washed with water (100 mL) and dried the wet material under vacuum at 60-65°C to obtain title compound. Wt: 120 gm; Purity by HPLC: 99.3%.

EXAMPLE-2:

Preparation of compound of Formula IV

Triphosgene (80 gm) and methylene chloride (700 mL) were added in to a round bottom flask at 25-35°C and stir for 10-20 min at same temperature. To the reaction mass was added compound of Formula II (100 gm) and sodium bicarbonate (135.7 gm) at 25-35°C and stir for 6 hrs at same temperature. After completion of the reaction, reaction mass was allowed to cool to 10-15°C and was added 40% aqueous monomethylamine (63 gm) at same temperature. Further, reaction mass was heated to 25-35°C and stir for 3 hrs at same temperature. After completion of the reaction, to the reaction mass was added water (600 mL) and concentrated under vacuum at 45-55°C. Then the reaction mass was allowed to cool to 25-35°C, was added methanol (100 mL) and stir for 2-3 hrs at same temperature. Filtered the solids and washed the wet cake with water (100 mL) and dry the wet material initially at 25-35°C for 60 min, then dry at 60-75°C for 6 hr to obtain title compound. Wt: 104 gm; Purity by HPLC: 99.5%.

EXAMPLE-3:

Preparation of compound of Formula IV

Compound of Formula I (100 gm) and methylene chloride (800 mL) were added in to a round bottom flask and stir for 10-20 min at 25-35°C. To the reaction mass was added Sulfuryl chloride (142.9 gm) was added slowly at 25-35°C and stir for 6 hrs at same temperature. After completion of the reaction, reaction mass was allowed to cool to 10-15°C and was added Triphosgene (53.8 gm) and sodium bicarbonate (277.2 gm) at same temperature. Reaction mass was heated to 25-35°C and stir for 6 hrs at same temperature. After completion of the reaction, reaction mass was allowed to cool to 10-15°C and was added 40% aqueous monomethylamine (61.6 gm) at same temperature. Further, reaction mass was heated to 25-35°C and stir for 3 hrs at same temperature. After completion of the reaction, to the reaction mass was added water (600 mL) and concentrated under vacuum at 45-55°C. Then the reaction mass was allowed to cool to 25-35°C, was added methanol (100 mL) and stir for 2-3 hrs at same temperature. Filtered the solids and washed the wet cake with water (100 mL) and dry the wet material initially at 25-35°C for 60 min, then dry at 60-75°C for 6 hr to obtain title compound. Wt: 100 gm.

EXAMPLE-4:

Preparation of Chlorantraniliprole

3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (100 gm), compound of Formula IV (68.95 gm) and acetonitrile (500 ml) were added in to a round bottom flask at 25-35°C and stir for 15 min at same temperature and was added 3-picoline (80 gm) at same temperature. Reaction mass was allowed to cool to -3±3°C and was added mesyl chloride (45.44 gm) at same temperature. Reaction mass was heated to 30±5°C and allowed to stir for 3 hrs at same temperature. After complete the reaction, water (100 ml) was added to the reaction mass and allowed to cool to 0±5°C and stir for 3 hrs at same temperature. Filtered the solids and washed with water (100 ml), dried the wet material under vacuum at 60-70°C to obtain title compound. Wt.: 146 gm.

It will be understood that various modifications may be made to the embodiments disclosed herein. Therefore the above description should not be constructed as limiting, but merely as exemplifications of preferred embodiments. For example, the functions described above and implemented as the best mode for operating the present invention are for illustration purposes only. Other arrangements and methods may be implemented by those skilled in the art without departing from the scope and spirit of this invention. Moreover, those skilled in the art will envision other modifications within the scope and spirit of the specification appended hereto.
,CLAIMS:WE CLAIM:

1. An improved process for preparation of compound of Formula IV, comprising:

Formula IV
a) reacting a compound of Formula I with a source of chloride in a suitable solvent to obtain a compound of Formula II,

Formula I Formula II
b) reacting the compound of Formula II with phosgene or its derivative and a suitable base to obtain a compound of Formula III, and

Formula III
c) reacting the compound of Formula III with a source of monomethyl amine to obtain a compound of Formula IV.

2. The process as claimed in claim 1, wherein the steps a) to c) are carried out in one-pot reaction without isolating the intermediates of Formula II and Formula III as solid.

3. The process as claimed in claim 1, wherein the steps b) and c) are carried out in one-pot reaction without isolating the intermediate of Formula III as solid.

4. The process as claimed in claim 1, wherein in the source of chloride is selected from the group consisting of sulfuryl chloride, N-chlorosuccinimide, chlorine gas, metal chloride-H2O2 in acid aqueous medium, HCl-H2O2, m-chloroperbenzoic acid/HCl and acetyl chloride.

5. The process as claimed in claim 1, wherein in the suitable solvent is selected from the group consisting of dimethylacetamide, dimethylformamide, N-methylpyrrolidone, ethyl acetate, methyl acetate, acetone, methyl isobutyl ketone, methyl ethyl ketone, acetonitrile, propionitrile, tetrahydrofuran, methyl tetrahydrofuran, dimethyl ether, diisopropyl ether, methyl tertiary butyl ether, 1,4-dioxane, methylene chloride, ethylene chloride, chloroform, toluene, xylene and mixture thereof.

6. The process as claimed in claim 1, wherein in the phosgene or its derivative is selected from the group consisting of phosgene, diphosgene, triphosgene and bromophosgene.

7. The process as claimed in claim 1, wherein in the suitable base is selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, potassium bicarbonate, triethylamine, isopropyl ethylamine, diisopropyl amine, diisopropyl ethylamine, N-methyl morpholine, piperidine, 2-picoline, 3-picoline and mixtures thereof.

8. The process as claimed in claim 1, wherein in the source of monomethyl amine is selected from the group consisting of aqueous methyl amine, methyl amine in solvent and methyl amine gas.

9. The process as claimed in claim 1, wherein in the source of chlorideissulfuryl chloride; the solvent is ethyl acetate, acetonitrile or methylene chloride; wherein the phosgene or its derivative is triphosgene; wherein the base is sodium carbonate, sodium bicarbonate or potassium bicarbonate; and wherein the source of monomethyl amine is aqueous methyl amine or methyl amine gas.

10. An improved process for preparation of compound of Formula IV, comprising:

Formula IV

a) reacting a compound of Formula I with a source of chloride in a suitable solvent to obtain a compound of Formula II,

Formula I Formula II
b) adding water and a suitable base to the step a) reaction mass,
c) optionally, concentrating the solution,
d) isolating the compound of Formula II,
e) reacting the compound of Formula II with phosgene or its derivative and a suitable base in a suitable solvent to obtain a reaction solution of compound of Formula III,

Formula III
f) reacting thesolution of compound of Formula III of step e) with a source of monomethyl amine,
g) adding water to the step f) reaction mass,
h) optionally, concentrating the solution,
i) optionally, adding an organic solvent to the step h) reaction mass, and
j) isolating the compound of Formula IV.

11. The process as claimed in claim 10, wherein the source of chlorideissulfuryl chloride; wherein the solvent in step a) and e) is ethyl acetate, acetonitrile or methylene chloride; wherein the base in step b) is sodium hydroxide; wherein the phosgene or its derivative is triphosgene; wherein the base in step e) is sodium carbonate, sodium bicarbonate or potassium bicarbonate; wherein the source of monomethyl amine is aqueous methyl amine or methyl amine gas; and wherein the organic solvent in step i) is methanol, ethanol or isopropanol.

Dated this 28th day of December, 2021

Rajeshwari H. – IN/PA-358
Agent for the Applicant
of Rajeshwari & Associates