Category: Triazoles

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. 288-88-0, name is 1H-1,2,4-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 288-88-0

(1) Sodium hydride (60% dispersion in mineral oil, 13.8 g, 345 mmol) was washed with hexane and suspended in DMF (150 ml). At an ice bath temperature, 1,2,4-triazole (total; 20.7 g, 300 mmol) was added thereto in four divisions. After stirring for 30 minutes, to the mixture was added tritylchloride (total; 83.7 g, 300 mmol) in seven divisions and additionally added DMF (50 ml). After stirring for 1.5 hours at room temperature, to the reaction mixture was added water (600 ml). The precipitated crystal was collected by filteration, washed with water, dissolved in CHCl3(800 ml) and dried. The solvent was evaporated. The obtained residue was chromatographed on silica gel (ethyl acetate: CHCl3= 1: 2, v/v). The fraction of the objective was concentrated to give 1-trityl-1H-1,2,4-triazole (43.9 g). Yield: 47%.

The synthetic route of 288-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1219607; (2002); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 23579-79-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 3,5-dibromo-l-methyl-lH-l,2,4-triazole (CAS 23579-79-5; 1 g, 4.15 mmol) at r.t. in DMF (15 ml) under an argon atmosphere was added pyrrolidine (310 mg, 360 mu, 4.36 mmol). The mixture was heated to 125C for 1 day. The mixture was cooled to r.t., diluted with EtOAc and washed with H20. The aqueous phase was back extracted with EtOAc. The combined organics were washed with H20 and brine, dried over MgS04, filtered and con- centrated. The crude product was purified by silica gel chromatography using a CH2Cl2/MeOH 9: 1 as eluent, providing the title compound (451 mg, 44%) as brown oil. MS: M = 231.1 (M+H)+

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; LERNER, Christian; WO2014/72261; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 135242-93-2, These common heterocyclic compound, 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, 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.

To a mixture of (1 -methyl-1 H-1 ,2, 4-triazol-3-yl)methanol (400 mg, 3.54 mmol) and iodobenzene diacetate (1 .25 g, 3.89 mmol) in dichloromethane (1 0 mL) was added TEMPO ((2,2,6,6-tetramethylpiperidin-1 -yl)oxyl) (56 mg, 354 muetaiotaomicronIota). The mixture was stirred at 1 5- 20C for 2h. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate = 1 :2) to give 1 -methyl-1 H-1 ,2,4-triazole-3- carbaldehyde (300 mg, 2.70 mmol, 76% yield).1H NMR (chloroform-c 400 MHz) delta 1 0.01 (s, 1 H), 8.1 9 (s, 1 H), 4.06 (s, 3H).

Statistics shows that (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol is playing an increasingly important role. we look forward to future research findings about 135242-93-2.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (270 pag.)WO2018/7249; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 60166-43-0, A common heterocyclic compound, 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, molecular formula is C4H7N3, 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.

A mixture of 7-bromo-5-nitroisoquinolin-1(2H)-one (2b, 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 potassiumacetate (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 to room temperature, the reaction mixture was partitioned between ethyl acetate (300 mL) and water (300 mL). The organic phase was separated, washed with brine (300 mL), dried over sodium sulfate, concentrated to dryness, and purified by silica gel chromatography(eluting with a gradient of 0%-i 0% methanol in ethyl acetate), affording 7-(i 4-dimethyl- iH-i,2,3-triazol-5-yl)-5-nitroisoquinolin-i(2H)-one (2c, 2.55 g, 60%) as a solid. 1H NMR (400 MHz, DMSO-d6) oe 11.95 (br. s., 1 H), 8.57 (5, 2H), 7.55 (d, J=5.38 Hz, 1 H), 6.98 (d, J=7.34 Hz, iH), 4.00 (5, 3H), 2.29 (5, 3H). MS: 284 [M-i].

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; PFIZER INC.; KUMPF, Robert Arnold; KUNG, Pei-Pei; SUTTON, Scott Channing; WYTHES, Martin James; (138 pag.)WO2015/193768; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1157938-97-0, name is 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1157938-97-0

To a solution of diisopropylamine (11 g) in dry THF (100 ml) 1.6 M solution of butyllithium in hexane (63 ml) was slowly added at -78 C. under nitrogen atmosphere. The mixture was allowed to warm up to -30 C., then re-cooled to -78 C. before propionitrile (5.4 g) was slowly added (exothermic reaction, cooling). The mixture was stirred at this temperature for ca. 15 min, 1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (10 g) was added, the reaction mixture warmed up to -20 C. within ca. 1 hr and finally poured on aqueous solution of phosphate buffer (pH 7). The aqueous phase was extracted 3 times with ethylacetate (300 ml) and the combined organic phase was twice with water, dried with sodium carbonate, filtered and evaporated under reduced pressure providing the title compound: 9 g. The analytical data were identical with published in U.S. Pat. No. 6,300,353 and WO99/45008 for (2S,3R)-enantiomer.

According to the analysis of related databases, 1157938-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Carbo-Design LLC; US2011/87030; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 16681-70-2, A common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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.

M. (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid 3-methyl-butyl ester (R4=H; R7=-(CH2)2-CH(CH3)2) (2S,4R)-4-Amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid (76 mg, 242 mumol) in MeCN (0.4 mL, 8 mmol) and 4 M HCl in 1,4-dioxane (242 muL, 969 mumol) was combined with 3-methyl-butan-1-ol (0.5 mL) at 60 C. The resulting mixture was stirred until solid precipitation was observed (~30 minutes). The solvent was evaporated under vacuum and the solids were azeotroped in toluene and dried under vacuum. 1,2,3-Triazole-4-carboxylic acid (0.0274 g, 0.242 mmol), DIPEA (169 muL, 969 mumol) and HATU (92 mg, 242 mumol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with the dried solids, predissolved in DMF (0.2 mL) and DIPEA (0.5 eq.). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product was purified by preparative HPLC and lyophilized to yield the title compound (28 mg; purity 95%). MS m/z [M+H]+ calc’d for C27H34N4O4, 479.26. found 479.4.

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 25537-64-8,Some common heterocyclic compound, 25537-64-8, name is 4,5-Dibromo-1-methyl-1,2,3-triazole, molecular formula is C3H3Br2N3, 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.

Butyl lithium 1.6M in hexanes (3.89 mL, 6.23 mmol) was added dropwise over 5min to a solution of 4,5-dibromo-l-methyl-lH-l,2,3-triazole (1 g, 4.15 mmol) in THF (20 mL) at – 75 C, maintaining the temperature <-70C. The resulting mixture was then stirred for 1 hr at - 78C. DMF (1.607 mL, 20.76 mmol) was then added and the mixture stirred for 30 min before being allowed to warm to room temperature. The reaction was quenched with 1M HCl (10 mL) and extracted with ether (3x50 mL). The combined organics were washed with brine (20 mL), dried over sodium sulphate, filtered and concentrated in vacuo. Purification was by silica gel chromatography (eluted with 0-50% ethyl acetate/isohexane) to give 4-bromo-l -methyl- 1H- l,2,3-triazole-5-carbaldehyde as a white solid (M+H30 207.9; LCMS method 2). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,5-Dibromo-1-methyl-1,2,3-triazole, its application will become more common. Reference:
Patent; IRM LLC; NOVARTIS AG; TELLEW, John Edward; WANG, Xia; WAN, Yongqin; XIE, Yun Feng; PAN, Shifeng; JIANG, Jiqing; XIE, Yongping; HUNT, Thomas Anthony; EDWARDS, Lee; BEATTIE, David; HEALY, Mark Patrick; WEST, Ryan; LISTER, Andrew Stuart; WO2012/138648; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 15294-81-2, 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 15294-81-2 as follows.

Iodomethane (1.819 mL, 29.1 mmol) was added cautiously to a suspension of 4,5- dibromo-lH-l,2,3-triazole (4.4 g, 19.40 mmol) and potassium carbonate (5.36 g, 38.8 mmol) in THF (20 mL) at room temperature. The resulting mixture was stirred overnight. The reaction was poured into water (50 mL) and extracted with ethyl acetate (3×100 mL). The combined organics were washed with brine (50 mL), dried over sodium sulphate, filtered and concentrated in vacuo. Purification was by silica gel chromatography (eluted with a 0-50percent ethyl acetate/isohexane) to give 4,5-dibromo-l-methyl-lH-l,2,3-triazole as a white solid (M+H 239.7; LCMS method 2).

According to the analysis of related databases, 15294-81-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; NOVARTIS AG; TELLEW, John Edward; WANG, Xia; WAN, Yongqin; XIE, Yun Feng; PAN, Shifeng; JIANG, Jiqing; XIE, Yongping; HUNT, Thomas Anthony; EDWARDS, Lee; BEATTIE, David; HEALY, Mark Patrick; WEST, Ryan; LISTER, Andrew Stuart; WO2012/138648; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 3179-31-5,Some common heterocyclic compound, 3179-31-5, name is 1H-1,2,4-Triazole-3-thiol, molecular formula is C2H3N3S, 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.

Step B–Cyclobutylmethyl 1,2,4-Triazol-3-yl Sulfide To a solution of 1,2,4-triazole-3-thiol (20.2 g; 0.20 mol) and sodium methoxide (11.8 g; 0.22 mol) in methanol (250 ml) is added cyclobutylmethyl methanesulfonate (36.4 g; 0.22 mol). The mixture was refluxed for 27 h under dry nitrogen, allowed to cool to 25 C. and filtered. The solid was washed with ethyl acetate and the organic solutions combined and evaporated. The residue was dissolved in water (250 ml) and extracted into ethyl acetate (250 ml) and dichloromethane (100 ml). The extracts were combined, dried (Na2 SO4), filtered and evaporated to afford crude cyclobutylmethyl 1,2,4-triazol-3-yl sulfide (21.8 g; 65%) as a white, sticky solid. NMR -d(CDCl3; 60 MHz) 1.5-2.8 (m), 3.2 (2H, d, J=7 Hz), 8.0 (1H, s) and 12.4 (1H, br s).

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

Reference:
Patent; Rohm and Haas Company; US5308830; (1994); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 4922-98-9, 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 4922-98-9 as follows.

Into a 50-mL round-bottom flask, was placed 3-phenyl-lH-l,2,4-triazol-5-amine (246 mg, 1.54 mmol, 1.00 equiv) in DMF (15 mL), HOBT (311 mg, 2.30 mmol, 1.50 equiv), EDCI (440 mg, 2.30 mmol, 1.50 equiv) and triethylamine (466 mg, 4.61 mmol, 3.00 equiv). Then 6-fluoro-l,2,3,4-tetrahydroquinoline-4-carboxylic acid (300 mg, 1.54 mmol, 1.00 equiv) was added in 2 mins later. The resulting mixture was stirred for 3 h at room temperature (25 ¡ãC). The reaction was then poured into 50 mL of water. The resulting solution was extracted with ethyl acetate (70 mL x 3), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied on a silica gel column and eluted with ethyl acetate/hexane (3/10). The collected fraction was concentrated to give 136.6 mg (26percent) of (5-amino-3- phenyl-lH-l,2,4-triazol-l-yl)(6-fluoro-l,2,3,4-tetrahydroquinolin-4-yl)methanone (17) as an off-white solid. MS (ES, m/z) [M+H]+: 338; HNMR (DMSO-^6, 300MHz ,ppm): delta 8.05- 8.00 (m, 2H), 7.70 (s, 2H), 7.53-7.48(m,3H), 6.89-6.79 (m, 2H), 6.55-6.52 (m, 1H), 5.87 (s, 1H), 4.95 (m, 1H), 3.26-3.18 (m, 2H), 2.23-2.145 (m, 1H), 2.13-2.08 (m, 1H).

According to the analysis of related databases, 4922-98-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE ROCKEFELLER UNIVERSITY; BRESLOW, Jan L.; PONDA, Manish P.; SELNICK, Harold; EGBERTSON, Melissa; (61 pag.)WO2017/123518; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics