Triazoles

288-88-0, Name is 1H-1,2,4-Triazole, 288-88-0, 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.

Example 1; Preparation of l-(4-NitrophenylmethyI)-l,2,4-triazole (i); Preparation of sodium triazole dihydrate; Into a IOOL glass flask were charged 50L of isopropanol and 2.9kg of sodium hydroxide flakes. The reaction mass was heated to 70C. After maintaining for 30min at same temperature lH-l,2,4-triazole (5.0kg) was added to the reaction mass. The reaction mass was maintained at reflux temperature for lhr. Slowly cooled the reaction mass to 30C and maintained for 3hr. The reaction mass was filtered and the wet cake washed with 5L of isopropanol. The wet material was dried at 600C until a constant weight is reached. Yield of sodium 1,2,4-triazole is 6.5kg.

Statistics shows that 1H-1,2,4-Triazole is playing an increasingly important role. we look forward to future research findings about 288-88-0.

Reference:
Patent; NATCO PHARMA LIMITED; PULLA REDDY, Muddasani; SATYASRINIVAS, Hanumara; RADHARANI, Kagitha; VENKAIAH CHOWDARY, Nannapaneni; WO2006/137083; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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.

Intermediate 60: 2,3-Dimethoxy-6-[1 ,2,3]triazol-2-yl-benzoic acid.To a 20 ml microwave vial containing 2-bromo-4,5-dimethoxybenzoic acid (3 g, 1 1 .5 mmol), copper iodide (0.04 g, 0.5 mol%), cesium carbonate (7.5 g, 23 mmol), triazole (1 .33 mL, 23 mmol) and finally (R,R)-(-)-N,N’-dimethyl-1 ,2- cyclohexanediamine ligand (0.36 mL, 2.3 mmol) was added DMF (12 mL). The resulting clumpy yellow slurry was stirred until evenly dispersed then heated to 120 C for 10-20 min using a microwave. At this point the reaction mixture appeared as a blue slurry which was then diluted with 20 mL ether and 20 mL H2O. The resulting solution was thoroughly stirred and transferred to a seperatory funnel then the RBF was subsequently rinsed with 20 mL ether and H2O each. The aqueous layer was separated from the organic layer and acidified to pH 1 with 6 ml_ cone. HCI. The now brown/ lime green aqueous layer was extracted twice with EtOAc. The bright yellow organic layers were combined and dried with Na2SO4 and then cone, into a yellow powder under reduced pressure which was purified by FCC (0-5% MeOH in DCM w/ 0.5% AcOH) to afford 2,3-dimethoxy-6-[1 ,2,3]triazol-2-yl-benzoic acid (60%) and 2,3- dimethoxy-6-[1 ,2,3]triazol-1 -yl-benzoic acid (20%). Data for 2,3-dimethoxy-6- [1 ,2,3]triazol-2-yl-benzoic acid, MS (ESI): mass calculated for CnHnN3O4, 249.23; m/z found 250.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.87 (s, 2H), 7.47 (s, 1 H), 7.18 (s, 1 H), 3.94 (s, 3H), 3.91 (s, 3H).Intermediate 61 : 2,3-Dimethoxy-6-[1 ,2,3]triazol-1 -yl-benzoic acid.The title compound was isolated from the procedure used to prepareIntermediate 60 with a 20% yield. MS (ESI): mass calculated for Cn Hn N3O , 249.23; m/z found 250.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.17 (d, J = 1 .0 Hz, 1 H), 7.82 (d, J = 1 .0 Hz, 1 H), 7.62 (s, 1 H), 7.09 (s, 1 H), 3.95 (s, 3H), 3.91 (s, 3H).

According to the analysis of related databases, 1H-1,2,3-Triazole, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, Name is 1H-1,2,3-Triazole, 288-36-8, 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.

Step 2. Tert-butyl 3-(1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate; A 1000-mL 4-necked round-bottomed flask was charged with a solution of 2H-1,2,3-triazole (30 g, 434.78 mmol, 1.00 equiv) in benzene (500 mL). To this solution was added chlorotrimethylsilane (49.3 g, 456.48 mmol, 1.05 equiv) drop wise 0 C. followed by addition of triethylamine (48.3 g, 478.22 mmol, 1.10 equiv). The resulting solution was stirred for 16 hours at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. The crude product was purified by distillation and the fraction was collected at 140-150 C. affording 2-(trimethylsilyl)-2H-1,2,3-triazole as colorless oil (11 g, 18%). To a solution of 2-(trimethylsilyl)-2H-1,2,3-triazole (6.2 g, 43.97 mmol, 2.74 equiv) in DMF (100 mL) was added tert-butyl 3-(4-nitrophenylsulfonyloxy)piperidine-1-carboxylate (6.2 g, 16.06 mmol, 1.00 equiv). The resulting solution was refluxed for 3 hours. Upon completion, the mixture was cooled down to room temperature and concentrated on a rotary evaporator affording tert-butyl 3-(1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate as brown solid (2.3 g).

Statistics shows that 1H-1,2,3-Triazole is playing an increasingly important role. we look forward to future research findings about 288-36-8.

Reference:
Patent; Kalypsys, Inc; US8080566; (2011); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7411-23-6, 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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) and p-quinonemethide precursor 7 (2.9 mmol) were refluxed for 4 h in DMF (10mL). Products were isolated analogously to compound 4a.

The synthetic route of 3,5-Dibromo-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 584-13-4, name is 4H-1,2,4-Triazol-4-amine, 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 584-13-4, 584-13-4

12.78 grams of sodium hypochlorite solution (36mM available chlorine) was dissolved inthe solution formed by mixing 5 mL glacial acetic acid with 30 mL of deionized water and the solution was cooled to 7 C. To this was added 1.5 g (18 mM) 4-amino-1,2,4-triazole dissolved in 15 mL deionized water. The solution was stirred at 7 C for 4 h followed by standing the final solution two days at room temperature. Yellow and oblong crystal of atrz (Supplemental data, figure S1) was obtained in 75% yield (scheme 1). This is very good for the synthesis of atrz, because the separation of the product, we know, always is the most difficult step during the whole synthetic experiment. In addition, sodium chloride, totally environment friendly, will only be left after atrz is separated from the final solution. Caution: The light, which makes sodium hypochlorite turn into sodium chloride and oxygen, must be obstructed during the whole reaction. Temperature is also very important to the yield of atrz because sodium hypochlorite is very unstable at high temperature (>25 C).Anal. Calcd for C4N8H4: C, 29.24; N, 68.32; H, 2.44. Found: C, 28.93; N, 68.36; H, 2.49. IR(cm-1) = 3111(s), 1489(s), 1368(s), 1315(m), 1176(s).

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, 4H-1,2,4-Triazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li; Wu; Qiu; Zhang; Yang; Journal of Coordination Chemistry; vol. 67; 11; (2014); p. 2016 – 2027;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, Name is 1-Methyl-1H-1,2,3-triazole, 16681-65-5, 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.

l-Methyl-5-tributylstannanyl-lH-[l,2,3]triazole; To a solution of 1 -methyl- lH-[l,2,3]triazole (1.33 g, 16 mmol) in THF (20 mL) at -78 0C, was added dropwise n-BuLi (11 mL,1.6M, 18 mmol). The mixture was stirred at -78 0C for 2 h before addition of Bu3SnCl (4.75 mL, 17.6 mmol). The mixture was stirred at this temperature for 1 h and at r.t. for 1 h. The mixture was concentrated in vacuo and hexanes was added. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo to afford l-methyl-5-tributylstannanyl-lH- [l,2,33triazole (6.12 g, 82% yield) as a yellow syrup.

Statistics shows that 1-Methyl-1H-1,2,3-triazole is playing an increasingly important role. we look forward to future research findings about 16681-65-5.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/108591; (2006); 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. 16681-65-5

Step 3: (S)-Methyl 3-(1 -methyl- 1H- 1 ,2,3-triazol-5-yl)-5-(phenyl(tetrahydro- 2H-pyran-4-yl)methyl)-5H-pyrido [3,2-bjindole-7-carboxylateA dry, N2 (g) flushed, 1 dram vial was charged with tetramethylammonium acetate (33.3 mg, 0.250 mmol), bis(triphenylphosphine)palladium dichloride (8.79 mg, 0.0130 mmol) and (S)-methyl 3 -bromo-5 -(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H- pyrido[3,2-b]indole-7-carboxylate (60.0 mg, 0.125 mmol). To this was added 1-methyl- 1H-1,2,3-triazole (20.8 mg, 0.250 mmol). The vial was again flushed with nitrogen. Tothis was added NMP (0.5 mL). The resulting mixture was stirred vigorously under a stream of nitrogen for 10 mm. The vial was placed in a pre-heated oil bath at 95 C and heated at that temperature overnight. The reaction was cooled to room temperature, diluted with EtOAc, washed with water (2X), then brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (100% EtOAc – 1%MeOH/EtOAc) to give 39.5 mg (66%) as an off-white solid. ?H NMR (500MHz, CDC13)o 8.61 (d, J1.6 Hz, 1H), 8.50 (s, 1H), 8.47 (d, J8.2 Hz, 1H), 8.10 (d, J=8.2 Hz, 1H),7.82 (s, 1H), 7.75 (s, 1H), 7.53-7.45 (m, 2H), 7.42-7.35 (m, 2H), 7.35-7.30 (m, 1H), 5.63(d,J10.7 Hz, 1H), 4.11-4.03 (m, 4H), 3.98 (s, 3H), 3.86 (dd,J=11.7, 3.0 Hz, 1H), 3.57(td,J=11.9, 1.7 Hz, 1H), 3.37 (td,J=11.9, 1.9 Hz, 1H), 3.22-3.09 (m, 1H), 2.11-2.01 (m,1H), 1.72-1.59 (m, 1H), 1.50-1.38 (m, 1H), 1.07 (d,J13.1 Hz, 1H). LCMS (M+H) =482.3.

The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, 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 7170-01-6. 7170-01-6

250A. 5-(3-Methyl-lH-l,2,4-triazol-l-yl)isoquinoline: A mixture of 5- bromoisoquinoline (0.500 g, 2.403 mmol), 3-methyl-lH-l,2,4-triazole (0.599 g, 7.21 mmol), K2C03 (0.996 g, 7.21 mmol), and Cul (0.458 g, 2.403 mmol) in MP (5.0 mL) was heated at 150 C overnight. The reaction mixture was cooled to room temperature, filtered through a plug of CELITE, filter cake washed with 10% MeOH/DCM, filtrate absorbed onto silica gel, purified by reverse phase prep. HPLC, and concentrated to give a white solid (80 mg, 16%). XH NMR (400MHz, methanol-d4) delta 9.43 (d, J = 0.7 Hz, 1H), 8.83 (s, 1H), 8.57 (d, J = 6.2 Hz, 1H), 8.35 (d, J = 8.4 Hz, 1H), 7.99 (dd, J = 7.3, 1.1 Hz, 1H), 7.90 – 7.81 (m, 2H), 2.55 (s, 3H) ppm. MS (ESI) m/z: 211 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3-Methyl-1H-1,2,4-triazole.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; SMITH, II, Leon M.; ORWAT, Michael J.; JEON, Yoon; CORTE, James R.; WO2014/160668; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, A common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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.

Method B: 2-Fluoro-6-[1 ,2,3]triazol-2-yl-benzoic acid. To a 2 L, 3- necked, round-bottomed flask equipped with an overhead mechanical stirrer, thermocouple probe, heating mantle, reflux condenser, and nitrogen inlet were added 2-fluoro-6-iodobenzoic acid (127.6 g, 480 mmol), copper iodide (4.57 g, 24 mmol), and Cs2C03 (312.6 g, 959 mmol). To these solids were added dioxane (640 mL), then water (2.6 mL, 144 mmol), then 1 H-1 ,2,3-triazole (55.6 mL, 959 mmol), and finally frans-1 ,2-dimethylcyclohexane-1 ,2-diamine (15.1 mL, 96 mmol). The mixture was then warmed to 60 C for 30 min, then to 83 C for 30 min, and then to 100 C for 3 h. After the 3 h at 100 C, the mixture was cooled and then 1 L of MTBE and 1 L of water were added. After vigorous mixing, the layers were separated and the bottom aqueous layer was acidified to pH 1 .72 with -148 mL of concentrated hydrochloric acid. The aqueous was then extracted twice with EtOAc. The combined organic layers were dried over Na2S04, filtered, and concentrated to provide a dark oil. The oil was stirred overnight in EtOAc (450 mL) and the resulting precipitate was removed by filtration. The mother-liquors were concentrated to a brown solid (106.21 g, 75 wt% by quantitative HPLC, 79.7 g, 80%). 1H NMR (400 MHz, DMSO-d6): 8.22 – 8.13 (bs, 2H), 7.84-7.80 (m, 1 H), 7.74 – 7.65 (m, 1 H), 7.50 – 7.41 (m, 1 H).

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, A common compound: 288-36-8, name is 1H-1,2,3-Triazole, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

2H-1,2,3-Triazole (760 mg, 11 mmol) was added to a suspension of 2,3-dichloro-5-nitro-pyridine (965 mg, 5 mmol) and anhydrous potassium carbonate (1.03 g, 7.5 mmol) in THF (50 mL), and the mixture was stirred overnight at room temperature. The mixture was diluted with EtOAc (100 mL), washed with water and brine, and the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica chromatography (hexane: EtOAc = 5:1 to 1:1) to give the title compound (505 mg, 44%). ?H NMR (400 MHz, DMSO-d6): 9.39 (d, 1H), 9.15 (d, 1H), 8.34 (s, 2H).

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, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CORNELL UNIVERSITY; CHILDREN’S MEDICAL CENTER CORPORATION; DANA-FARBER CANCER INSTITUTE, INC; GRAY, Nathanael, S.; SCOTT, David, A.; HATCHER, John; DU, Guangyan; MELNICK, Ari, M.; GABAS, Lorena, Fontan; CASALENA, Gabriella; US, Ilkay; WU, Hao; QIAO, Qi; (178 pag.)WO2018/165385; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics