Category: Triazoles

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. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., Product Details of 7343-33-1

A mixture of K2C03 (29.19 g, 211.2 mmol), 3-bromo-1H-1,2,4-triazole (25 g, 169.0 mmol) and 2-chloropyrazine (19.36 g, 169.0 mmol) inNMP (130 mL) was heated at 125 ¡ãC for 6 hrs. The reaction was quenched with water (300 mL) and stined for lh. The solids were collected, washed with water, ether and dried to give 2-(3-bromo-1,2,4-triazol-1-yl)pyrazine (32 g, 83.8percent). ?H NMR (300 MHz, CD3OD+CDC13) oe 9.40 – 9.05 (m, 2H), 8.70 (d, J = 2.5 Hz, 1H), 8.56 (dd, J = 2.5, 1.5 Hz, 1H) ppm. ESI-MS m/z calc. 224.97, found 226.29 (M+1)+; Retention time: 0.75 minutes

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; VERTEX PHARMACEUTICALS INCORPORATED; DAVIES, Robert, J.; CAO, Jingrong; COCKERILL, Meghan, Elise; COLLIER, Philip, Noel; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GAO, Huai; GOLDMAN, Brian, Anthony; GREY, Ronald, Lee; GRILLOT, Anne-laure; GU, Wenxin; HENDERSON, James, A.; IRARRAZAVAL, Raul Eduardo, Krauss; KOLPAK, Adrianne, Lynn; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MALTAIS, Francois; MESSERSMITH, David; PIERCE, Albert, Charles; PEROLA, Emanuele; RYU, Elizabeth Jin-Sun; SYKEN, Joshua; WANG, Jian; (706 pag.)WO2016/197009; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Methyl-1H-1,2,4-triazole

The solution of compound 1 (30 g, 0.13 mol) in THF (1.5 L) was cooled to -78 C. Then a solution of vinyl magnesium in THF (508 mL, 1N, 0.51 mol) was added dropwise to the above solution maintained below -40 C. The mixture was stirred for 3 hrs at -78 C before being quenched with saturated aqueous NH4Cl solution. The layers were separated, the aqueous layer was extracted with EtOAc (3¡Á500 mL) and the combined organic layer was washed with brine and concentrated. The crude product was purified by silica gel column chromatography to obtain compound 2 (5 g, 17%). Compound 2 (4.0 g, 17.2 mmol) was dissolved in freshly prepared NaOMe (20 mL). CuI (3.2 g, 17.2 mmol) was added to the above solution. The mixture was stirred at 110 C under microwave for 3 hrs. After the mixture was completed, the mixture was added EtOAc and H2O, then the suspension was filtered, the filtrate was separated. The organic layer was concentrated to give crude product which was purified by column chromatography to give compound 3 (1.8 g, 45%). A mixture of compound 3 (0.7 g, 3.8 mmol) and 3-methyl-1,2,4-triazole (6.4 g, 76.8 mmol) was added copper powder (0.49 g, 7.68 mmol) and KOH (0.43 g, 7.68 mmol). The mixture was heated tomelt at 170-175 C under N2. After the starting material was consumed completely, the mixture was added EtOAc and H2O, then the suspension was filtered, the filtrate was separated. The organic layer was concentrated to give crude product which was purified by column chromatography to give compound 4 (0.23 g, 26%). A solution of compound 4 (0.23 g, 1 mmol) in THF (12 mL) was cooled to -10 C, EtMgBr (0.47 g, 3.5 mmol)was added dropwise at -10 C followed by the addition of pyridine(0.3 mL). The slurry was cooled to -45 C, and the ethyl 2-chloro-2-oxoacetate (0.55 g, 4 mmol) was added dropwise at -45 C. The slurry was allowed to -10 C and stirred at this temperature for 1h. After the reaction was completed, the mixture was quenched with IPA (2mL) and H2O (20 mL). The mixture was extracted with EtOAc, the organic layer was washed with brine and concentrated to give crude product which was purified by column chromatographyto give compound 5 (0.17 g, 52%). A solution of compound 5 (0.17 g, 0.52mmol) in MeOH (5 mL) was added NaOH (0.041 g, 1.03 mmol) and H2O (2mL). The mixture was stirred at 25 C for 6 hrs and then added 1N HCl to adjusted pH 6, the mixture was concentratedto give compound 6 (0.29 g) as crude product.

The synthetic route of 7170-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tuyishime, Marina; Lawrence, Rae; Cocklin, Simon; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 228 – 234;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 1338226-21-3, A common heterocyclic compound, 1338226-21-3, name is 3-(Chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one, molecular formula is C4H6ClN3O, its 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.

2-(tert-Butyl)-4-chloro-5-methylphenol (CAS: 30894-16-7, 250 mg), 3-(chloromethyl)-4- methyl-1H-1,2,4-triazol-5(4H)-one (CAS: 1338226-21-3; 279 mg), potassium carbonate (348 mg) and potassium iodide (20.9 mg) were combined in acetone (10.0 mL) at rt under an argon atmosphere. The mixture was then heated to reflux for 3 hours and was then kept at rt for another16 hours. TLC showed no residual starting material at that time. The reaction mixture was then poured into ice/water and the aqueous layer was extracted twice with ethyl acetate. The organic layers were washed once with brine, dried over Na2SO4, filtered and evaporated. The crude material was purified by flash chromatography on silica gel with 0% to 70% ethyl acetate in heptane as an eluent to provide the title compound as a colorless solid (60 mg). MS (mlz):310.2 [MH]?.

The synthetic route of 1338226-21-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; LUEBBERS, Thomas; MARTIN, Rainer E.; MATTEI, Patrizio; NEIDHART, Werner; RICHTER, Hans; RUDOLPH, Markus; PINARD, Emmanuel; (450 pag.)WO2017/37146; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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. Product Details of 956317-36-5

Compound (R)-I will be implemented in Preparation Example 1 -1 (5.54g, 20mmol, ee> 99%) is placed dichloro Methane (100 mL) and added triethylamine (12g, 120mmol), stirred for 1 hour at room temperature, mixing, Cooled to 0 C, the acid chloride solution prepared above was added dropwise to the mixture was slowly warmed to room temperature, After stirring for 16 hours. After completion of the reaction, adding 50mL of dichloromethane was added a saturated aqueous Aqueous sodium hydroxide (40 ml), the aqueous layer separated, the organic phase was washed with aqueous saturated sodium chloride, Dried over anhydrous magnesium sulfate to give a brown oil, ethyl acetate: n-heptane (volume ratio 5: 1) Decolorization and recrystallization to give a pale yellow waxy solid 7.4g, namely compound 10 in 95% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 956317-36-5, its application will become more common.

Reference:
Patent; CR Double-Crane Pharmaceuticals Co., Ltd; Liu, Kaixiang; Ma, Hongmin; Li, Kai; (22 pag.)CN105367506; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, 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. category: Triazoles

A mixture of 7-bromo-5-nitroisoquinolin-1(2H)-one (293b, 4.00 g, 14.9 mmol), 1,4-dimethyl-1H-1,2,3-triazole (2.17 g, 22.3 mmol), palladium acetate (334 mg, 1.49 mmol), CatacXiumA (butyl di-1-adamantylphosphine) (1.10 g, 2.97 mmol), and potassium acetate (7.30 g, 74.3 mmol) in 2-methyl-2-butanol (100 mL) was degassed with nitrogen, and heated at 120 C. in a sealed tube overnight. After cooling down room temperature, the reaction mixture was partitioned between ethyl acetate (300 mL) and water (300 mL). The organic phase was separated, washed with brine (1*300 mL), dried over sodium sulfate, concentrated to dryness, and purified by silica gel chromatography (eluting with a gradient of 0%-10% methanol in ethyl acetate), affording 7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one (293c, 2.55 g, 60% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) delta 11.95 (br. s., 1H), 8.57 (s, 2H), 7.55 (d, J=5.38 Hz, 1H), 6.98 (d, J=7.34 Hz, 1H), 4.00 (s, 3H), 2.29 (s, 3H). MS: 284 [M-1].

The synthetic route of 60166-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; EDWARDS, Martin Paul; KUMPF, Robert Arnold; KUNG, Pei-Pei; MCAPLINE, Indrawan James; NINKOVIC, Sacha; RUI, Eugene Yuanjin; SUTTON, Scott Channing; TATLOCK, John Howard; WYTHES, Martin James; Zehnder, Luke Raymond; US2014/179667; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7343-33-1,Some common heterocyclic compound, 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, molecular formula is C2H2BrN3, 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.

Method 1: Diacetoxycopper (2.30 g, 12.7 mmol), 3,5-difluorophenyl-boronic acid (1.60 g, 10.1 mmol), 3-bromo-1H-1,2,4-triazole (1.25 g, 8.4 mmol) and 4A molecular sieve (150mg) were mixed in DCM (50 mL), and pyridine (1.3 mL, 16.90 mmol) was added. The mixture was stined at RT under air for 3 days. LCMS showed that no starting material remained and desired product was formed. The reaction was filtered through a plug of Celite via suction and the solid was washed with additional DCM (200m1). The combined organic layer was washed with 0.1 N aqueous HC1 three times (50 ml x 3) and brine (200 ml). The organic layer was concentrated and purified on silica gel (120 g column, dry loading method on Celite) using 10-90percent EtOAc:Hexanes to afford 1.23 g (50percent) of desired product JW-lc. ?H NMR (400 MHz, DMSO-d6) oe 9.40 (s, 1H), 7.78 – 7.61 (m, 2H), 7.41 (tt, J = 9.3, 2.3 Hz, 1H) ppm. ESI-MS m/z calc. 258.95566, found 260.05 (M+1)+; Retention time: 0.8 minutes.

The synthetic route of 7343-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; DAVIES, Robert, J.; CAO, Jingrong; COCKERILL, Meghan, Elise; COLLIER, Philip, Noel; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GAO, Huai; GOLDMAN, Brian, Anthony; GREY, Ronald, Lee; GRILLOT, Anne-laure; GU, Wenxin; HENDERSON, James, A.; IRARRAZAVAL, Raul Eduardo, Krauss; KOLPAK, Adrianne, Lynn; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MALTAIS, Francois; MESSERSMITH, David; PIERCE, Albert, Charles; PEROLA, Emanuele; RYU, Elizabeth Jin-Sun; SYKEN, Joshua; WANG, Jian; (706 pag.)WO2016/197009; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 342617-08-7, 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 342617-08-7 as follows.

Step 2: [3-(3-Bromophenyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate A slurry of 3-(3-bromophenyl)-1H-1,2,4-triazole (58.5 g; 261 mmol; Step 1 above), anhydrous K2CO3 (43.2 g; 313 mmol), and chloromethylpivalate (45 mL; 313 mmol) in dry MeCN (250 mL) was heated to 80 C. (Note 1) for 1 hour. The mixture was cooled, solid was collected by filtration and the filtrate was concentrated in vacuo. Residue from the filtaret was combined with the filtered solid and the whole was stirred with water approximately 20 minutes. Solid was collected by filtration, washed with water (*3) and recrystallized from MeOH/water, affording the title compound as a colorless solid. LC/MS (method E) tR 0.88 min, m/z 338, 340 (M+H, Br isotopes).

According to the analysis of related databases, 342617-08-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smithkline Beecham Corporation; US2011/124559; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 103755-58-4,Some common heterocyclic compound, 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, molecular formula is C9H9N3O, 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.

General procedure: 1-Azido-4-methylbenzenes 1 (0.3 mmol), propargyl alcohol 2 (0.36 mmol), CuI (0.03 mmol),NaAsc (0.06 mmol), and 2 mL solvent were added to a 15 mL pressure tube. The tube was thensealed, and the mixture was stirred at 80 C for 5 hours. After the reaction completed, the abovesystem was added with KMnO4 (0.75 mmol) and Na2CO3 (0.45 mmol), and stirred at 80 C for 8h until the reaction completed. Then, Ag2O (0.03 mmol) and K2S2O7 (0.6 mmol) were added tothe tube and the mixture was conducted at 100 C for 24 h until the transformation finished byTLC analysis. H2O (25 mL) was added to the mixture and the system was extracted with EtOAc (3¡Á 20 mL). The combined organic layer was washed with brine (3 ¡Á 5 mL), dried with Na2SO4, andconcentrated under reduced pressure to afford the crude product. Purification by columnchromatography on silica gel with EtOAc-PE (1:3) afforded the desired product 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, its application will become more common.

Reference:
Article; Han, Chunmei; Dong, Suping; Zhang, Wensheng; Chen, Zhen; Synlett; vol. 29; 5; (2018); p. 673 – 677;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 423165-07-5, A common heterocyclic compound, 423165-07-5, name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, molecular formula is C13H22N4, its 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.

General procedure: To an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C.

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:
Article; Viveka, T. Lakshmi; Sharada, L. Nalanda; Asian Journal of Chemistry; vol. 30; 9; (2018); p. 2029 – 2034;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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