Tag: M.W=0-100

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

288-88-0, 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, 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.

2-(2H-1.2,3-triazol-2-yl>5-methylbenzoic acid (A-3)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), CsCO3 (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 1200C 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 Na2SO^ filtered and concentrated. The residue was purified by gradient elution on Sitheta2 (0 to 10% MeOH in water with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-3, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. Data for A-3 : 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.

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

Reference:
Patent; MERCK & CO., INC.; WO2008/8518; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

41253-21-8, Adding some certain compound to certain chemical reactions, such as: 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, 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 41253-21-8.

At room temperature, a four-necked bottle was charged with 120 g of acetonitrile, 1,2,4-triazole sodium salt (18.20 g, 0.2 mol), 2,4′-dichloroacetophenone (37.80 g, 0.2 mol) , heating to 80~85 C, heat preservation reaction 1-2h, the reaction is completed, the solvent is evaporated to dryness under reduced pressure, 50g of water is added, extracted with 150g of dichloromethane, washed with water, the solvent is dried, to obtain a white solid qualitative content of 98% The weight yield is 96%.

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 41253-21-8.

Reference:
Patent; Huai’an Guorui Chemical Co., Ltd.; Wu Yaojun; Zhang Pu; Zhao Wei; Jin Yucun; Wang Fengyun; Chen Mingguang; Mao Gengsheng; (6 pag.)CN109535091; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

41253-21-8, 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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, This compound has unique chemical properties. The synthetic route is as follows.

Compound 271; Synthesis of N-(5-(lH-l.Z4-triazol-l-ylV2-f3A5-trimethoxybenzovn phenvPacetamide; As shown in Reaction 1, first, magnesium was added to l-bromo-3,4,5- trimethoxybenzene as a starting material. Then, Compound (VII) derivative was added thereto to obtain a compound [N-(5-fluoro-2-(3,4,5- trimethoxybenzoyl)phenyl)acetamide. Thus obtained compound [N-(5-fluoro-2- (3,4,5-trimethoxybenzoyl)phenyl)acetamide] (36.2mg, 0.1 mmol) was dissolved in DMF (2 ml), and 1,2,4-triazole-Na (28.5 mg) was added thereto at room temperature. The mixture was heated with stirring for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with an EtOAc solution. The organic layer was washed with water, and brine. The extracted organic layer was dried over anhydrous MgSO4, and the solid substance was filtered off. The remaining solvent was removed by vacuum evaporation. The resulting residue was purified by column chromatography (SiO2, n-Hex/EA=2/l?l/l) to obtain Compound 271 (25.6 mg, 65%).1H NMR (CDCl3) delta 10.812 (s, IH), 9.077 (s, IH), 8.788 (s, IH), 8.144 (s, IH), 7.767 (d, J = 8.36 Hz, IH), 7.564 (d, J = 8.52 Hz, IH), 6.956 (s, 2H), 3.954 (s, 3H), 3.879 (s, 6H), 2.264 (s, 3H). MS (ESI) m/z 397 (M+ + H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; WO2008/38955; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-34-2, Adding a certain compound to certain chemical reactions, such as: 7343-34-2, name is 3,5-Dimethyl-4H-1,2,4-triazole, 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 7343-34-2.

General procedure: A mixture of 1 g of 4-chloromethyl-1-(4-chloro-phenyl)-1H-[1,2,3]triazole, 0.5 g of 3,5- dimethyl-1H-[1,2,4]triazole and 1 g of potassium carbonate in 20 ml of DMF were stirred for 2 days. After filtration and evaporation of the solvent the crude product was purified by flash chromatography to form 0.6 g of the title compound (M+H+ 289.7, melting range 153-156 ¡ãC).

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

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; SCHINDLER, Rudolf; LANKAU, Hans-Joachim; HOeFGEN, Norbert; EGERLAND, Ute; LANGEN, Barbara; DOST, Rita; WARD, Simon; (89 pag.)WO2016/25917; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 16681-65-5, name is 1-Methyl-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. 16681-65-5

a 3-Methyl-3 H-1,2,3-triazole-4-carboxaldehyde To a stirred solution of 1-methyl-1 H-1,2,3-triazole (0.500 g, 6.02 mmol) in anhydrous THF (20 ml), cooled to -70 C. under nitrogen, was added dropwise a 1.6 M solution of butyl lithium in hexanes (4.23 ml, 6.77 mmol). The mixture was stirred at this temperature for 1 h, then anhydrous DMF (0.465 ml, 6.02 mmol) was added, and the mixture was allowed to warm to 0 C. over 30 min. Saturated aqueous NH4Cl (25 ml) was then added and the mixture was extracted with ethyl acetate. The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 40% EtOAc/hexane) to give 0.128 g (19%) of the title compound as a yellow oil: 1H NMR (360 MHz, d6-DMSO) delta4.27 (3 H, s), 8.45 (1 H, s), 10.01 (1 H, s); MS (ES+) m/e 144[M+MeOH+H]+, 111[M]+.

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, 16681-65-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Limited; US6255305; (2001); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, These common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, 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.

Compound 10 (62.0 g, 115 mmol), Pd2 (dba) 3 (21.0 g, 22.9 mmol), dppf (14.0 g,25.2mmol), Cs2CO3 (112g, 344mmol),3-Methyl-1H-1,2,4-triazole (21.0 g, 252 mmol) was mixed in toluene (600 mL), stirred and warmed to reflux for 4 hr.After cooling, tap water (600 mL) was added and liquid separation was carried out. The organic phase is dried,Crystallization from petroleum ether gave compound 11 (41.9 g, 77.5%).

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 7170-01-6.

Reference:
Patent; Liu Fengjuan; (8 pag.)CN108623631; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, These common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, 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.

3-Methyl-iH-i,2,4-triazole (375 mg, 4.51 mmol) was placed in a flask with dry DMF (5 mL).Sodium hydride (195 mg, 4.89 mmol) was added and the RM was stirred at room temperature for 15 minutes. tert-Butyl 4-((methylsulfonyl)oxy) pi peridi ne-i -carboxylate (Intermediate C, step 1) (i.OOg, 3.S8mmol) was then added and the RM was stirred at 10000 for 4 hours. The resulting mixture was partitioned between EtOAc and water. The organic phase was washed with water and brine, dried over Mg504, filtered and the solvent wasremoved in vacuo. The product was purified by chromatography on silica eluting with isohexane/( EtOAc:MeOH – 10:1) to afford:Product Step 1 a: tert- Butyl 4-(3-methyl- 1 H- 1,2 ,4-triazol- 1 -yl)piperidine- 1 -carboxylate;1H NMR (400 MHz, DMSO-d6) O 8.40 (iH, 5), 4.48 (iH, m), 4.01 (2H, m), 2.90 (2H, m), 2.22(3H, 5), 1.99 (2H, m), 1.72 (2H, m), 1.40 (9H, 5).Product Step 1 b: tert- Butyl 4-(5-methyl- 1 H- 1,2 ,4-triazol- 1 -yl)piperidine- 1 -carboxylate;1H NMR (400 MHz, DMSO-d6) O 7.79 (iH, 5), 4.45 (iH, m), 4.02 (2H, m), 2.90 (2H, m), 2.41 (3H, 5), 1.82 (2H, m), 1.75 (2H, m), 1.41 (9H, 5).

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 7170-01-6.

Reference:
Patent; NOVARTIS AG; BEATTIE, David; BAETTIG, Urs; LEGRAND, Darren Mark; LISTER, Andrew Stuart; MCKENNA, Jeffrey; PEARCE, David William; SANDHAM, David Andrew; STEWARD, Oliver Ross; THOMSON, Christopher; WO2015/8230; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, The chemical industry reduces the impact on the environment during synthesis 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, I believe this compound will play a more active role in future production and life.

Procedure A To a flask containing 1-methyl-1H-1,2,3-triazole (400 mg, 4.81 mmol, prepared according to PCT Int. Appl., 2008098104) was added THF (25 mL) and the colorless solution was cooled to -50 C. Then, n-BuLi (2.5 M in hexanes, 1.88 mL) was added drop wise which afforded a dark reddish-brown solution. The mixture was allowed to warm gradually to -10 C. over 30 minutes, then a solution of (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (750 mg, 1.58 mmol, Intermediate 49: step b) in THF (5 mL) was introduced at -10 C. The reaction mixture became a dark brown color and was allowed to warm gradually to room temperature. The mixture was stirred for 60 minutes at room temperature, then quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc-THF (?10:2, v/v) 5*50 mL. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to provide a brown foam. Chromatography on silica gel (5% MeOH-DCM increasing to 10% MeOH) provided the title compound as a yellow solid. MS m/e 557.2 [M+H]+. 1H NMR (500 MHz, CDCl3) delta 8.23 (d, J=1.8 Hz, 1H), 7.72 (d, J=8.7 Hz, 1H), 7.49 (d, J=11.5 Hz, 2H), 7.38 (d, J=8.0 Hz, 3H), 7.30 (s, 1H), 7.06 (d, J=5.9 Hz, 1H), 5.99 (s, 1H), 4.33-4.19 (m, 2H), 4.06 (s, 3H), 3.88 (s, 3H), 3.33 (s, 3H), 2.14 (s, 3H). The racemic material was separated into its individual enantiomers using the following conditions: Chiralpack OD column; 80% heptanes: 20% ethanol; wavelength=242 nM to provide the two enantiomers. The first eluting enantiomer was Example 80B and the second eluting enantiomer was Example 80C.

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

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics