Triazoles

Reference of 288-36-8, 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 288-36-8 as follows.

Example 120: Preparation of 4,5-dibromo-lH-pi,2,31triazoleRr Br. BrN^ NH *” ‘ \V NVNH To a solution of IH-[1, 2,3]triazole (1.26 ml, 21.7 mmol) in water (10 ml) at 5tfC, was added bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at 5CPC for 1.5 hours. The white solid (2.375 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (1.83 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (375 mg) was isolated via filtration and washed with water (5ml). The white solids were combined and dried to give 4,5-dibromo- IH-[1, 2,3]- triazole (4.92 g, 93percent yield). M.p. 194.7C.

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA LIMITED; WO2007/96576; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, belongs to Triazoles compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 16681-70-2, Recommanded Product: 1H-[1,2,3]Triazole-4-carboxylic acid

Step 2: Tert-butyl 4-(2-(N-methyl-1H-1,2,3-triazole-4-carboxamido)ethyl)piperidine-1-carboxylate To 1H-1,2,3-triazole-4-carboxylic acid (150 mg, 1.327 mmol) and tert-butyl 4-(2-(methylamino)ethyl)piperidine-1-carboxylate (step 1) (322 mg, 1.327 mmol) in DMF (6 ml) was added DIPEA (0.695 ml, 3.98 mmol) and 50% T3P in DMF (1.549 ml, 2.65 mmol). The resulting orange solution was stirred for 4 hrs. The mixture was diluted with EtOAc (200 ml) and washed with 1M HCl (2*50 ml). The organics were dried (MgSO4) and concentrated under reduced pressure. The crude residue in was dissolved in DCM and applied to a 12 g silica cartridge eluting with 0-100% EtOAc/iso-hexane. The product fractions were concentrated to give tert-butyl 4-(2-(N-methyl-1H-1,2,3-triazole-4-carboxamido)ethyl)piperidine-1-carboxylate as a gum. LCMS: Rt=1.01 mins; MS m/z 338.5 [M+H]+; Method 2minLowpHv01

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, 1H-[1,2,3]Triazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Novartis AG; Legrand, Darren Mark; Furminger, Vikki; Thomson, Christopher; Hughes, Owen Rhys; Stanley, Emily; US2014/171403; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, 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. Application In Synthesis of Methyl 1H-1,2,4-triazole-3-carboxylate

EXAMPLE 3 A mixture of methyl 1,2,4-triazole-3-carboxylate (26.4 g, 0.21 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (60.2 g, 0.19 mole) was melted and then 1.1 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 3 hours, while maintaining the temperature of the reaction mixture at 105+-5¡ã C. And then, the reaction mixture was crystallized with 300.8 ml of methanol to give 58.6 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 80percent).

The synthetic route of 4928-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 59660-30-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 59660-30-9 name is (4-Methyl-4H-[1,2,4]triazol-3-yl)methanol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of (4-methyl-l,2,4-triazol-3-yl)methanol (45.83 mg, 0.41 mmol), 5-[4- (trifluoromethoxy)phenyl]-3H-oxazolo[4,5-b]pyridin-2-one (60 mg, 0.20 mmol), PPI13 (106.26 mg, 0.41 mmol) and DIAD (81.92 mg, 0.41 mmol) in THF (3 mL) was stirred at 20 C under N2 for 16 hours. The reaction was diluted with sat.NH4Cl (10 mL), and the mixture was extracted with EtOAc (10 mL x 2). Then the combined organic phase was washed with brine (10 mL), dried over Na2SC>4, filtered and concentrated to give the crude product. The crude product was purified by Prep-HP LC (Waters Xbridge (150 mm x 25 mm, 5 muiotaeta) A = H20 (10 mM NH4HCO3) and B = CH3CN; 32 – 47% B over 8 minutes) to give the impure product. The impure product was triturated from z-Pr20 (10 mL) and purified by Prep-HP LC (Waters Xbridge (150 mm x 25 mm, 5 muiotatauiota) A = H20 (10 mM NH4HCO3) and B = CH3CN; 33 – 63% B over 6 minutes) to give the product (16.59 mg, 41.1 muiotatauiotaomicron, 20% yield) as a solid. 1H NMR (DMSO-c 400MHz) deltaH = 8.48 (s, 1H), 8.14 (d, 2H), 7.88 (d, 1H), 7.81 (d, 1H), 7.48 (d, 2H), 5.30 (s, 2H), 3.79 (s, 3H). LCMS Rt = 1.10 min in 2.0 min chromatography, MS ESI calcd. for CnHnFjNsOs [M+H]+ 392.1, found 391.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (4-Methyl-4H-[1,2,4]triazol-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Formula: C3H5N3

General procedure: Methyl 2,6-difluoro-4-{[(4-iodophenyl)sulfonyl]amino}benzoate (4.5 g, 9.9 mmol) was dissolved in N-methylpyrrolidone (90 ml), and 1,2,3-triazole (1.50 g, 21.7 mmol), copper(I) iodide (1.20 g, 6.30 mmol), potassium phosphate (6.0 g, 28 mmol), and trans-N,N?-dimethylcyclohexane-1,2-diamine (1.50 g, 10.5 mmol) were added thereto, followed by stirring at 145 C. for 12 hours in the presence of nitrogen gas. After cooling to room temperature, the reaction solution was diluted with water, followed by extraction with ethyl acetate (150 ml¡Á5). The extraction liquids were combined, washed with saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. Then, the solvent was removed. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=2:1 to 1:1) to obtain methyl 2,6-difluoro-4-({[4-(1H-1,2,3-triazol-1-yl)phenyl]sulfonyl}amino)benzoate (M-17) (650 mg, 17%) and methyl 2,6-difluoro-4-({[4-(2H-1,2,3-triazol-2-yl)phenyl]sulfonyl}amino)benzoate (M-18) (800 mg, 20%). The title compound (252 mg, 4%) was obtained as a white solid by subjecting methyl 2,5-difluoro-4-[(4-iodophenyl)sulfonylamino]benzoate (7.00 g, 15.5 mmol) and 4-methyl-1H-triazole (2.50 g, 30.1 mmol) to the same methods as in Examples 15 to 18. [1338] 1H NMR (400 MHz, DMSO-d6): delta 11.18 (s, 1H), 8.67 (s, 1H), 8.15 (m, 2H), 8.06 (m, 2H), 7.68-7.63 (m, 1H), 7.34-7.29 (m, 1H), 3.80 (s, 3H), 2.33 (s, 3H)

The synthetic route of 27808-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. Recommanded Product: 5-Bromo-1H-1,2,4-triazole

An HMPA (45.01 mL) solution of 3-bromo-1H-1,2,4-triazole (4.439 g, 30 mmol) was treated with 1,3,5-trifluorobenzene (approximately 39.62 g, 300.0 mmol) and potassium carbonate (approximately 4.146 g, 30.00 mmol). The reaction mixture was stirred in a Q-tube at 112 ¡ãC overnight. To the reaction mixture was added ethyl acetate and brine. The organic phase was dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure. The crude material was purified by silica gel chromatography (80 g column; 20percent ethyl acetate/heptane). The desired fractions were concentrated to dryness under reduced pressure to yield 3-bromo-1-(3,5-difluorophenyl)-1,2,4-triazole (5.7 g, 21.92 mmol, 73percent). 1H MR (400 MHz, OMSO-de) delta 9.39 (s, 1H), 7.77 – 7.57 (m, 2H), 7.39 (tt, J = 9.3, 2.3 Hz, 1H) ppm. ESI-MS m/z calc. 258.95566, found 260.05 (M+l)+; Retention time: 0.8 minutes

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7343-33-1, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BETHIEL, Randy Scott; CAO, Jingrong; COLLIER, Philip, N.; DAVIES, Robert J.; DOYLE, Elisabeth; FRANTZ, James Daniel; GOLDMAN, Brian Anthony; GREY, Ronald Lee; GRILLOT, Anne-laure; GU, Wenxin; KOLPAK, Adrianne Lynne; KRAUSS, Paul Eduardo; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MESSERSMITH, David; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; WANG, Jian; (491 pag.)WO2018/106646; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 288-36-8, name is 1H-1,2,3-Triazole, A new synthetic method of this compound is introduced below., category: Triazoles

[0260] Bromine (11.59 g, 73.35 mmol) was added dropwise to a 0 C solution of 2H-l,2,3-triazole (5.00 g, 72.46 mmol) in water (50 mL), and the resulting solution was allowed to warm to room temperature and stir overnight. The precipitate was collected by filtration and dried to afford 4,5- dibromo-2H-l ,2,3-triazole (8.00 g, 49%) as a white solid. MS (ESI, pos. ion) m/z 228, 226, 230 [M+H]+.

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; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 49607-51-4,Some common heterocyclic compound, 49607-51-4, name is 1-Methyl-1H-1,2,4-triazol-3-amine, molecular formula is C3H6N4, 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.

4-chloro-7-isothiocyanate-7-de (acetamide)colchicine (54 mg, 0.12 mmol) was dissolved in DMF (1 mL). 3-amino-1-methyl-1H-1,2,4-triazole (15 mg, 0.12×1.2mmol) was added, and stirred at 80 degrees C overnight. The solvent was distilled off after the reaction. Chloroform was added and washed with saturated sodium bicarbonate solution, dried with magnesium sulfate and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (Biotage Isolera One, SANP 25 g, chloroform/methanol) to obtain title compound (a yellow solid, 42 mg, 65.8percent) .

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

Reference:
Patent; CHIBA UNIVERSITY; YAKULTHONSHA COMPANY LIMITED; TAKAYAMA, HIROMITSU; YASOBU, NAOKO; KITAJIMA, MARIKO; YAEGASHI, TAKASHI; MATSUZAKI, TAKESHI; NAGAOKA, MASATO; HASHIMOTO, SHUSUKE; NISHIYAMA, HIROYUKI; SUGIMOTO, TAKUYA; ONO, MASAHIRO; (176 pag.)JP5829520; (2015); B2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 288-36-8 name is 1H-1,2,3-Triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), Cs2CO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dimethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-5, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. Data for A-5: 1HNMR (500 MHz, DMSO-d6) d 12.98 (br s , IH), 8.04 (s, 2H), 7.72-7.45 (m, 3H), 2.41 (s, 3H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-1,2,3-Triazole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; COLEMAN, Paul, J.; SCHREIER, John, D.; WO2010/48014; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 7411-23-6, The chemical industry reduces the impact on the environment during synthesis 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life.

In a 50 mL round bottomed flask sodium hydride (60% dispersion in mineral oil) (132 mg, 3.31 mmol) was added to a colorless solution of 3,5-dibromo- lH-l,2,4-triazole (Int-1, 500 mg, 2.2 mmol) in DMF (7 ml). The resulting suspension was stirred at room temp during 30 min and 3,3,3-trifluoropropyl 4-methylbenzenesulfonate (591 mg, 2.2 mmol) solved in DMF (3 ml) was added and the reaction was stirred at 40C over night. The reaction mixture was poured into 50 mL H20 and extracted with EtOAc (3 x 50 mL). The organic layers were washed with sat NaCl (3 x 50 mL), dried over MgS04 and concentrated in vacuo. The title compound was isolated as a light yellow liquid (288 mg, 40.5 % yield). MS (ES+) m/z: 323.8 [(M+H)+].

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, 3,5-Dibromo-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics