The origin of a common compound about 1533519-84-4

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 1533519-84-4, The chemical industry reduces the impact on the environment during synthesis 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, I believe this compound will play a more active role in future production and life.

Ethanol 535g was first added to a 1L four-necked flask at room temperature.Compound IV (106.9 g, 0.4 mol) was added with stirring and compound Vb (66.9 g, 0.22 mol) was added.Slowly warm up to 50-55C under nitrogen protection. The solid dissolves completely.Potassium bicarbonate 48 g was added in portions over 60-80 minutes. After the addition, the reaction is incubated at 50-55C for 2-3 hours.The disappearance of the TLC monitoring point indicates the end of the reaction.After the reaction was completed, insoluble material was removed by hot filtration, and the resulting filtrate was slowly cooled to -5C.A large number of white solids precipitated, and 100 ml of deionized water was added dropwise to the reaction flask over 1-2 hours to crystallize sufficiently.And remove inorganic salts. After deionized water is added, it is crystallized at -5C for 2 hours and filtered.The filter cake was washed with 100 ml of 95% ice-cold ethanol. The resulting compound (IIIa) was vacuum-dried,Dry at a temperature of 50-55C for 24 hours. 127.2 g of compound (IIIa) was obtained in a yield of 94%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Xin Donggang Pharmaceutical Co., Ltd.; Yan Jianbo; Ma Liangxiu; Lin Yi; Hong Huabin; (16 pag.)CN107739344; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Share a compound : 1533519-84-4

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, A new synthetic method of this compound is introduced below., Formula: C15H13N3S

Ethanol 535g was first added to a 1L four-necked flask at room temperature.Compound IV (106.9 g, 0.4 mol) was added with stirring and Compound Va (47.3 g, 0.22 mol) was added.Slowly warm up to 50-55C under nitrogen protection. The solid dissolves completely.Potassium bicarbonate 48 g was added in portions over 60-80 minutes. After the addition, the reaction is incubated at 50-55C for 2-3 hours.The disappearance of the TLC monitoring point indicates the end of the reaction.After the reaction was completed, insoluble material was removed by hot filtration, and the resulting filtrate was slowly cooled to -5C.A large number of white solids precipitated, and 100 ml of deionized water was added dropwise to the reaction flask over 1-2 hours to crystallize sufficiently.And remove inorganic salts. After deionized water is added, it is crystallized at -5C for 2 hours and filtered.The filter cake was washed with 100 ml of 95% ice-cold ethanol. The resulting compound (IIIa) was vacuum-dried,Dry at a temperature of 50-55C for 24 hours. 124.5 g of compound (IIIa) was obtained with a yield of 92%.

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Xin Donggang Pharmaceutical Co., Ltd.; Yan Jianbo; Ma Liangxiu; Lin Yi; Hong Huabin; (16 pag.)CN107739344; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The important role of 1533519-84-4

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, belongs to triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C15H13N3S

[0254] Charge dimethylformamide (2.63 kg ¡À 5% <> 2.8 L ¡À 5%) to a reactor. Heat the dimethylformamide to a temperature between 27C and 35C. Charge Compound 5 (1.0 kg ¡À 1%) to the same reactor in portions whilst maintaining the temperature between 27C and 35C. Add methyl bromoacetate (0.6008 / M x 100 kg ¡À 1% <> 0.3620 / M x 100 L ¡À 1%) to the reaction mixture whilst maintaining the temperature between 27C and 35C, e.g., between 28C and 33C, where M is the purity of the methyl bromoacetate by GC in % area. The methyl bromoacetate addition is slightly exothermic. [0255] Stir the mixture for at least 10 minutes and not more than 20 minutes, at a temperature between 27C and 35C, e.g., between 28C and 33C. [0256] Add to the reaction mixture sodium bicarbonate (0.314 kg ¡À 1%) in portions whilst maintaining the temperature between 27C and 35C, over a period of at least 30 minutes and not more than 70 minutes. During the portion additions of sodium bicarbonate gaseous carbon dioxide is released. [0257] Stir the mixture for at least 1 hour and not more than 4 hours, at a temperature between 27C and 35C, e.g., between 28C and 33C. Cool the reaction mixture to a temperature between 5C and 10C, and then sample for HPLC analysis. [0258] The reaction is considered complete if the content of Compound 5 is below 0.50% area by HPLC, preferentially below 0.20% area by HPLC. If reaction completion is not achieved after the second sample, heat the reaction mixture to a temperature between 27C and 35C. Add methyl bromoacetate (0.0172 / M x 100 kg ¡À 1% <> 0.0103 / M x 100 L ¡À 1%) to the reaction mixture whilst maintaining the temperature between 27C and 35C, e.g., between 28C and 33C. Stir the mixture for at least 30 minutes and not more than 2 hours, at a temperature between 27C and 35C, e.g., between 28C and 33C, then sample for HPLC analysis. [0259] If reaction is complete, add to the reaction mixture over at least 15 minutes, while maintaining the temperature between 5C and 20C, ozonated deionised water (9.0 L ¡À 5%). During the addition the gaseous carbon dioxide can be released. The ozonated deionised water addition is slightly exothermic. Stir the mixture for at least 30 minutes while maintaining the temperature between 5C and 10C. [0260] Add to the mixture, over at least 10 minutes, while maintaining the temperature between 5C and 20C, a solution previously prepared by dissolution of sodium bicarbonate (0.105 kg ¡À 1%) in ozonated deionised water (1.47 L ¡À 5%), until a pH of the mixture between 6.7 and 8.0, e.g., between 6.9 and 7.3. Stir the suspension for at least 60 minutes while maintaining the temperature between 5C and 10C. Filter the suspension. Wash the wet cake with ozonated deionised water (2.0 L ¡À 5%) previously cooled to a temperature between 5C and 10C, twice. [0261] Wash the wet cake with a mixture of ethyl acetate (0.09 kg ¡À 5% <> 0.1 L ¡À 5%) and isopropyl alcohol (0.79 kg ¡À 5% <> 1.0 L ¡À 5%) previously cooled to a temperature between 0C and 5C, twice. [0262] Dry the wet cake under vacuum at a temperature below 45C, until the water content (by Karl Fischer analysis) is lower than, or equal to, 0.5% w/w, preferentially lower than, or equal to, 0.1%) w/w, the content of ethyl acetate by GC is lower than, or equal to, 200 ppm, the content of isopropyl alcohol by GC is lower than, or equal to, 600 ppm and the content of dimethylformamide by GC is lower than, or equal to, 10000 ppm.

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; GUNIC, Esmir; GALVIN, Gabriel; WO2014/8295; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Introduction of a new synthetic route about 1533519-84-4

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

Related Products of 1533519-84-4,Some common heterocyclic compound, 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, molecular formula is C15H13N3S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 8. Preparation of methyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate [073] To a round bottom flask added 4-(4-cyclopropyl-l-yl)-4H-l, 2,4-triazole-3-thiophenol (54.0 g), acetone/water (500 mL/25 mL), methyl chloroacetate (17.8 mL) and potassium carbonate (33.5 g) to form a mixture, the mixture was heated to about 40C, after stirred for about 6 hours, the mixture was cooled to room temperature (about 19C), then was added water (about 400 mL), stirred for about 5 minutes followed by removing acetone, filtered, the filter cake was washed with water and dried in vacuum at about 50C for about 12 hours to obtain methyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate 65.0 g, yield 90%. LC-Ms: m/z (ESI): 402 (M+H)+, 1H MR (400 MHz, CDC13): delta 8.54 (d, J=8.0 Hz, 1 H), 8.32 (s, 1 H), 7.66 (m, 1 H), 7.54 (m, 1 H), 7.34-7.41 (m, 5 H), 7.23 (m, 1 H), 7.10 (m, 2H), 4.30 (dd, J=8.0, 12 Hz, 2 H), 2.43 (m, 1 H), 1.17 (m, 2 H), 0.86 (m, 2 H).

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CHEN, Weiqiang; LUO, Jian; LIU, Lixue; FAN, Yuping; WO2014/198241; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Brief introduction of 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione

According to the analysis of related databases, 1533519-84-4, the application of this compound in the production field has become more and more popular.

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1533519-84-4 as follows. Application In Synthesis of 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Example 10. Preparation of phenyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate [075] To a round bottom flask added 4-(4-cyclopropyl-l-yl)-4H-l,2,4-triazole-3-thiophenol (40.0 g), acetone (600 mL) and triethylamine (16.6 g) to form a mixture at room temperature, after stirred for 20 min, the mixture was cooled to 0C, then was added drop wise a solution of phenyl chloroacetate in isopropanol (33.8 g of phenyl chloroacetate was dissolved in 200 mL of acetone), during the addiction the mixture was maintained at about 0C, after the addition, the mixture was warm to 20C, after stirred for about 2 hours, the reaction was complete, filtered, and the filter cake was washed with acetone (100 mL), after filtration, the filter cake was added purified water (700 mL) to give a slurry, the slurry was stirred for 1 hour, then the purified water was removed by vacuum filtration, the filter cake was dried in vacuum at about 50C for about 24 hours to obtain phenyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate, yield 90% the HPLC purity(area) 99.2%.

According to the analysis of related databases, 1533519-84-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CHEN, Weiqiang; LUO, Jian; LIU, Lixue; FAN, Yuping; WO2014/198241; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some scientific research about 1533519-84-4

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, its application will become more common.

Electric Literature of 1533519-84-4,Some common heterocyclic compound, 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, molecular formula is C15H13N3S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of the compound of Formula (5) (30 g, 112.22 mmol) in N,N-dimethylformamide (94 mL) was charged sodium bicarbonate (18.39 g, 218.96 mmol) to provide a suspension. 1,2-Bis(chloroacetoxy)ethane (compound of Formula (4-A)) (11.77 g, 54.74 mmol) was then charged and the mixture stirred at room temperature for 72 hours. Following the completion of the reaction, the reaction mixture was poured into ice water (250 mL) over 10 minutes to form a slurry, which was warmed to room temperature and stirred for 1 hour. The product was then collected by filtration, washed with cold (0-5 C.) water (2*60 mL), and suction dried for 45 minutes to provide a damp cake. A new flask was charged with the damp cake along with dichloromethane (300 mL) and stirred at room temperature for 30 minutes to afford a clear, biphasic solution. The organic phase was removed and washed with water (2*120 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo at 30-35 C. The foamy solid was then dried in vacuo at room temperature for 24 hours to afford the compound of Formula (3-A) as a foamy light yellow solid (quantitative yield, HPLC purity=99.35 area %). 1H-NMR (CDCl3, 300 MHz) delta: 0.75-0.94 (4H, m), 1.10-1.22 (4H, m), 2.41 (2H, tt, J=5.64 Hz, 8.47 Hz), 4.08 (ABq, 4H, DeltadeltaAB=0.05, JAB=16.36 Hz), 4.34 (4H, s), 7.29-7.43 (6H, m), 7.57 (2H, apparent dt, J=1.23 Hz, 7.64 Hz), 7.66 (2H, apparent dt, J=1.23 Hz, 7.60 Hz), 8.28 (2H, s), 8.53 (2H, d, J=8.35 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, its application will become more common.

Reference:
Patent; Apotex Inc.; Bodhuri, Prabhudas; Green, Melanie R. A.; Karadeolian, Avedis; Weeratunga, Gamini; Gorin, Boris; (33 pag.)US2018/258057; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Brief introduction of 1533519-84-4

According to the analysis of related databases, 1533519-84-4, the application of this compound in the production field has become more and more popular.

Electric Literature of 1533519-84-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1533519-84-4 as follows.

The compound of Formula (4-B) (2.1 g, 6.53 mmol), the compound of Formula (5) (5.33 g, 19.92 mmol), sodium bicarbonate (2.19 g, 26.12 mmol) and N,N-dimethylformamide (10 mL) were combined in a flask and the resulting suspension was stirred at room temperature for 6 days. The reaction mixture (containing ?18 mol % of the compound of Formula (5) by 1H-NMR) was then poured onto ice water (60 mL) over 10 minutes whereupon a suspension formed. The formed suspension was stirred for 30 minutes during which time the solution was warmed to room temperature. The solid product was then collected by filtration, washed with water (4*8 mL), and suction dried for 15 minutes to provide a damp cake. A new flask was charged with the damp cake along with dichloromethane (75 mL), and the mixture stirred at room temperature for 30 minutes to afford a biphasic solution. The organic phase was removed and washed with water (3*30 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo at 30-35 C. to afford the compound of Formula (3-B) (5.78 g; 86% yield from the compound of Formula (4-B); HPLC purity=92 area %) as a light yellow foamy solid. 1H-NMR (CDCl3, 300 MHz) delta: 0.75-0.90 (6H, m), 1.15 (6H, d, J=8.50 Hz), 2.33-2.46 (3H, m), 3.96-4.20 (6H, m), 4.21-4.39 (4H, m), 5.27-5.36 (1H, m), 7.29-7.36 (6H, m), 7.36-7.43 (3H, m), 7.50-7.59 (3H, m), 7.59-7.68 (3H, m), 8.23 (1H, s), 8.25 (2H, s), 8.48-8.56 (3H, m).

According to the analysis of related databases, 1533519-84-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Apotex Inc.; Bodhuri, Prabhudas; Green, Melanie R. A.; Karadeolian, Avedis; Weeratunga, Gamini; Gorin, Boris; (33 pag.)US2018/258057; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some tips on 1533519-84-4

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, A new synthetic method of this compound is introduced below., Quality Control of 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Ethanol 620g was first added to a 1L four-necked flask at room temperature.Compound IV (106.9 g, 0.4 mol) was added with stirring and compound Vc (57 g, 0.22 mol) was added.Slowly warming to 50-55C under nitrogen protection, completely dissolved solids,Potassium bicarbonate 48 g was added in portions over 60-80 minutes. After the addition, the reaction is incubated at 50-55C for 2-3 hours.The disappearance of the raw material point monitored by TLC represents the end of the reaction.After the reaction was completed, insoluble material was removed by hot filtration, and the resulting filtrate was slowly cooled to -5C.A large number of white solids precipitated, and 100 ml of deionized water was added dropwise to the reaction flask over 1-2 hours to crystallize sufficiently.And remove inorganic salts. After deionized water is added, it is crystallized at -5C for 2 hours.Filter and filter cake washed with 100 ml of 95% ice-cold ethanol.The resulting compound (IIIb) was dried under vacuum and dried at a temperature of 50-55C for 24 hours.124 g of compound (IIIb) was obtained in a yield of 86%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Zhejiang Xin Donggang Pharmaceutical Co., Ltd.; Yan Jianbo; Ma Liangxiu; Lin Yi; Hong Huabin; (16 pag.)CN107739344; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Brief introduction of 1533519-84-4

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, A new synthetic method of this compound is introduced below., HPLC of Formula: C15H13N3S

Acetonitrile 600g is first added to a 1L four-neck flask at room temperature.Compound IV (106.9 g, 0.4 mol) was added with stirring.Compound Vc (57.9 g, 0.22 mol) was added. Slowly warm up to 50-55C under nitrogen protection.The solid was completely dissolved and 48g of potassium bicarbonate was added portionwise over 60-80 minutes.After the addition, the reaction was incubated at 50-55C for 3-4 hours. The disappearance of the raw material at TLC indicated that the reaction was complete.After the reaction was completed, insoluble material was removed by hot filtration, and the resulting filtrate was slowly cooled to -5C.A large number of white solids precipitated, and 50 ml of deionized water was added dropwise to the reaction flask over 1-2 hours to crystallize sufficiently.And remove inorganic salts. After deionized water is added, it is crystallized at -5C for 2 hours and filtered.The filter cake was washed with 100 ml of 95% glacial acetonitrile. The resulting compound (IIIc) was vacuum-dried,Dry at a temperature of 50-55C for 24 hours. 120.3 g of compound (IIIc) was obtained with a yield of 83%.

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Xin Donggang Pharmaceutical Co., Ltd.; Yan Jianbo; Ma Liangxiu; Lin Yi; Hong Huabin; (16 pag.)CN107739344; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 1533519-84-4

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C15H13N3S

[0254] Charge dimethylformamide (2.63 kg ¡À 5% <> 2.8 L ¡À 5%) to a reactor. Heat the dimethylformamide to a temperature between 27C and 35C. Charge Compound 5 (1.0 kg ¡À 1%) to the same reactor in portions whilst maintaining the temperature between 27C and 35C. Add methyl bromoacetate (0.6008 / M x 100 kg ¡À 1% <> 0.3620 / M x 100 L ¡À 1%) to the reaction mixture whilst maintaining the temperature between 27C and 35C, e.g., between 28C and 33C, where M is the purity of the methyl bromoacetate by GC in % area. The methyl bromoacetate addition is slightly exothermic. [0255] Stir the mixture for at least 10 minutes and not more than 20 minutes, at a temperature between 27C and 35C, e.g., between 28C and 33C. [0256] Add to the reaction mixture sodium bicarbonate (0.314 kg ¡À 1%) in portions whilst maintaining the temperature between 27C and 35C, over a period of at least 30 minutes and not more than 70 minutes. During the portion additions of sodium bicarbonate gaseous carbon dioxide is released. [0257] Stir the mixture for at least 1 hour and not more than 4 hours, at a temperature between 27C and 35C, e.g., between 28C and 33C. Cool the reaction mixture to a temperature between 5C and 10C, and then sample for HPLC analysis. [0258] The reaction is considered complete if the content of Compound 5 is below 0.50% area by HPLC, preferentially below 0.20% area by HPLC. If reaction completion is not achieved after the second sample, heat the reaction mixture to a temperature between 27C and 35C. Add methyl bromoacetate (0.0172 / M x 100 kg ¡À 1% <> 0.0103 / M x 100 L ¡À 1%) to the reaction mixture whilst maintaining the temperature between 27C and 35C, e.g., between 28C and 33C. Stir the mixture for at least 30 minutes and not more than 2 hours, at a temperature between 27C and 35C, e.g., between 28C and 33C, then sample for HPLC analysis. [0259] If reaction is complete, add to the reaction mixture over at least 15 minutes, while maintaining the temperature between 5C and 20C, ozonated deionised water (9.0 L ¡À 5%). During the addition the gaseous carbon dioxide can be released. The ozonated deionised water addition is slightly exothermic. Stir the mixture for at least 30 minutes while maintaining the temperature between 5C and 10C. [0260] Add to the mixture, over at least 10 minutes, while maintaining the temperature between 5C and 20C, a solution previously prepared by dissolution of sodium bicarbonate (0.105 kg ¡À 1%) in ozonated deionised water (1.47 L ¡À 5%), until a pH of the mixture between 6.7 and 8.0, e.g., between 6.9 and 7.3. Stir the suspension for at least 60 minutes while maintaining the temperature between 5C and 10C. Filter the suspension. Wash the wet cake with ozonated deionised water (2.0 L ¡À 5%) previously cooled to a temperature between 5C and 10C, twice. [0261] Wash the wet cake with a mixture of ethyl acetate (0.09 kg ¡À 5% <> 0.1 L ¡À 5%) and isopropyl alcohol (0.79 kg ¡À 5% <> 1.0 L ¡À 5%) previously cooled to a temperature between 0C and 5C, twice. [0262] Dry the wet cake under vacuum at a temperature below 45C, until the water content (by Karl Fischer analysis) is lower than, or equal to, 0.5% w/w, preferentially lower than, or equal to, 0.1%) w/w, the content of ethyl acetate by GC is lower than, or equal to, 200 ppm, the content of isopropyl alcohol by GC is lower than, or equal to, 600 ppm and the content of dimethylformamide by GC is lower than, or equal to, 10000 ppm.

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; GUNIC, Esmir; GALVIN, Gabriel; WO2014/8295; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics