Day: January 19, 2021

Adding a certain compound to certain chemical reactions, such as: 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, 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 103755-58-4, Computed Properties of C9H9N3O

General procedure: A 10mL microwave tube was loaded with6a(1.4mmol), paraformaldehyde (4mmol), the appropriate alcohol (4.5mmol) and were irradiated for 20min. The internal temperature reached 150C. The alcohol excess was evaporated under reduced pressure. The residual solid product was purified by column chromatography on silica gel and eluted with an increasing polarity gradient mixture of hexane and ethyl acetate (9/1). For the product 7e was used 5mL of chloroform as solvent.

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, (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jordao, Alessandro K.; Novais, Juliana; Leal, Bruno; Escobar, Ana C.; Dos Santos Junior, Helvecio M.; Castro, Helena C.; Ferreira, Vitor F.; European Journal of Medicinal Chemistry; vol. 63; (2013); p. 196 – 201;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7170-01-6, 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 7170-01-6 as follows.

Example 4; Preparation of Compound C’ from Compound B’ (Example 2); Compound B’ (60.00 g, 0.274 mol) (prepared as in Example 2) was added in portions to a melt of 3-methyl-1,2,4-triazole (113.8 g, 1.369 mol) under argon at 110-120 C. The mixture was heated to about 143 C. and the resulting solution was stirred at 142-44 C. for 17 h. After cooling to 120 C., 1-methyl-2-pyrrolidinone (NMP) (60 mL) was added quickly. The solution was further cooled to about 95 C. and water (300 mL) was added slowly (about 30 min.) keeping the temperature at 85 and 95 C. resulting in crystallization of the product. The slurry was cooled slowly to 0-5 C. and held for about 1 h. The cold slurry was filtered and the cake washed with cold H2O (2¡Á75 mL) then dried in vacuo at 55 C. for 16 h affording 34.5 g Compound C’ as a crystalline, tan solid (54.9%), HPLC AP 98.2. If necessary, the product could be further purified by recrystallization from ethyl acetate. 1H NMR (400 MHz, CDCl3) delta 2.55 (s, 3H), 4.05 (s, 3H), 6.73 (dd, 1H, J=2.9, 2.6), 7.42 (dd, 1H, J=2.9, 2.8), 7.57 (s, 1H), 9.16 (s, 1H), 10.29 (bs, 1H). Anal. Calcd for C11H11N5O: C, 57.63; H, 4.84; N, 30.55. Found: C, 57.37; H, 4.74; N, 30.79.

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293304; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 288-36-8,Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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.

Intermediate 41 : 5-Fluoro-2-[1 ,2,3]triazol-2-yl-benzoic acid.5-Fluoro-2-[1 ,2,3]triazol-2-yl-benzoic acid. To a solution of 5-fluoro-2-iodo- benzoic acid (3.86 g, 14.65 mmol), 2H-[1 ,2,3]triazole (2.5 g, 36.2 mmol), CS2CO3 (8.62 g, 24.5 mmol), trans-N, N’-dimethyl-cyclohexane-1 ,2-diamine (0.4 ml_), Cul (244 mg) and DMF (13 ml_) were added to a microwave ready vessel and heated to 100 C for 10 min. The mixture was cooled, diluted with water, and extracted with EtOAc. The aqueous layer was acidified and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1 %HOAc/DCM) gave the product as a white powder, (2.14 g, 71 %). 1H NMR (400 MHz, CD3OD): 7.91 (s, 2H), 7.76 (dd, J = 8.9, 4.8 Hz, 1 H), 7.59 (dd, J = 8.5, 2.9 Hz, 1 H), 7.49 – 7.42 (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; 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

16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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. COA of Formula: C3H3N3O2

Example 16 (R)-5-(5?-Chloro-2?-fluorobiphenyl-4-yl)-2-(2-hydroxyethyl)-2-hydroxymethyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid (isomers a and b) [0438] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)-propyl]-3-hydroxymethyl-dihydro-furan-2-one (isomer a; 10 mg, 30 mumol, 1.0 eq.) and DIPEA (30 muL, 170 mumol, 5.6 eq.) were dissolved in DMF (200 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 90 mumol, 3.0 eq.), DIPEA (60 muL, 340 mumol, 11.2 eq.) and HATU (15 mg, 40 mumol, 1.3 eq.), were dissolved in DMF (600 muL) and stirred at room temperature for a few minutes. The solutions were then combined and the resulting mixture stirred at room temperature and when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture, the organics were then separated and concentrated in vacuo. The crude residue was dissolved in a 1:1 solution of MeOH and aqueous 2N NaOH (4 mL), and stirred at room temperature for 30 minutes and when the reaction was complete (as determined by LC/MS analysis), the mixture was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer a; 3 mg). LCMS (ESI): calc. C23H24ClFN4O5=490; obs. M+H=491.2. Retention time: 2.04 min. [0440] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)-propyl]-3-hydroxymethyl-dihydro-furan-2-one (isomer b; 30 mg, 52 mumol, 1.0 eq.) and DIPEA (50 muL, 291 mumol, 5.6 eq.) were dissolved in DMF (200 muL). 1H-1,2,3-triazole-4-carboxylic acid (17 mg, 156 mumol, 3.0 eq.), DIPEA (100 muL, 582 mumol, 11.2 equiv.) and HATU (25 mg, 68 mumol, 1.3 eq.), were dissolved in DMF (600 muL) and stirred at room temperature for a few minutes. The solutions were then combined and the resulting mixture was stirred at room temperature; when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture. The organic layer was separated, concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer b; 3.9 mg). LCMS (ESI): calc. C23H24ClFN4O5=490; obs. M+H=491.2. Retention time: 1.99 min. [0441] LC/MS Method: flow rate: 1.5 mL/min; Buffer A: 0.1% TFA/H2O; Buffer B 0.1% TFA/MeCN; gradient elution from 5-100% B over 3.6 minutes, then 100% B for 1.0 minute, detection at 254 nm

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

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/209352; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 61-82-5, 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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 3-amino-1,2,4-triazole or benzimidazole (1.0 mmol), benzaldehyde (1.0 mmol), dimedone (1.0 mmol), and acetonitrile (5 mL) was taken in a round bottom flask and added iodine (10 mol %) and stirred at 80 C for 10 min. After completion of the reaction, as monitored by TLC, the reaction mass was cooled to room temperature and the solid separated was filtered and washed with water and dried at reduced pressure.Data of representative examples

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-1,2,4-Triazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Puligoundla, Ravinder Goud; Karnakanti, Shuklachary; Bantu, Rajashaker; Nagaiah, Kommu; Kondra, Sudhakar Babu; Nagarapu, Lingaiah; Tetrahedron Letters; vol. 54; 20; (2013); p. 2480 – 2483;,
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. 423165-07-5, name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 423165-07-5

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.

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 423165-07-5.

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

Application of 1001401-62-2,Some common heterocyclic compound, 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, molecular formula is C9H7N3O2, 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 4: (2-(2H-l,2,3-Triazol-2-yl)phenyl)((2i?,5i?)-5-hydroxy-2-methylpiperidin-l-yl)methanone (9) A solution of (3R, 6i?)-6-methylpiperidin-3-ol (5.31 g, 46.1 mmol), 2-(2H- 1 ,2,3- triazol-2-yl)benzoic acid (10.5 g, 55.3 mmol), EDC (17.7 g, 92.0 mmol), l-hydroxy-7- azabenzotriazole (12.6 g, 92.0 mmol), and triethylamine (19.3 mL, 138 mmol) in DMF (300 mL) was stirred at 50 C overnight, then diluted with saturated aqueous sodium bicarbonate and extracted 3x with ethyl acetate. The organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel gradient chromatography (0-100% ethyl acetate in hexanes), providing the title compound as a pale yellow solid. LRMS m/z (Mu+Eta) 287.3 found, 287.1 required.

The synthetic route of 1001401-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; LIVERTON, Nigel, J.; SKUDLAREK, Jason, W.; WO2014/176142; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7170-01-6, A common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, molecular formula is C3H5N3, 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 Zn(NO3)2.6H2O (30.0 mg, 0.1 mmol), 3-amino-1,2,4-triazole (8.4 mg, 0.1 mmol), H2bdc (8.3 mg, 0.05 mmol) and HNO3 (0.08 mL) in a mixed solvents of DMA (1.5 mL), MeOH(1.5 mL) and H2O (3 mL) was placed in a glass vial (23 mL) and heated at 100 C for 3 days. Colorless polyhedral crystals were obtained and washed with MeOH (yield: 75% based on ligand).Anal. Calc. (Found) for C12H11Zn2N8O4.5: C, 30.66 (30.62); H, 2.36(2.26); N, 23.84 (23.82)%. Selected IR data (KBr, cm-1): 3413,3337, 3231, 1633, 1588, 1541, 1390, 1404, 1290, 1227, 1067,1013, 885, 830, 746, 583.

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

Reference:
Article; Liu, Jie; Wei, Yuhui; Bao, Fenlin; Li, Guixiang; Liu, Huiyan; Wang, Haiying; Polyhedron; vol. 169; (2019); p. 58 – 65;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 61-82-5,Some common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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 aldehyde (1 mmol), dimedone (1 mmol), 3-amino-1,2,4-triazole (1 mmol), and [C4(H-DABCO)2][HSO4]4 (16 mg) washeated in an oil bath (90 C) under solvent-free conditions. Aftercompletion of the reaction, as identified by TLC, using n-hexane:EtOAc (7:3) as the eluent, 10 mL of water was added and stirredfor 10 min. The catalyst was dissolved in water and the solid wasfiltered off and washed with warm EtOH, to obtain the pure targetmolecule.

The synthetic route of 61-82-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Safari, Niloufar; Shirini, Farhad; Tajik, Hassan; Journal of Molecular Structure; vol. 1201; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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 16681-65-5 as follows. name: 1-Methyl-1H-1,2,3-triazole

To a flask containing 1-methyl-1H-1,2,3-triazole (200 mg, 2.41 mmol, prepared according to PCT Int. Appl., 2008098104) was added THF (20 mL) and the colorless solution was cooled to -40 C. Then, n-BuLi (2.5 M in hexanes, 1.0 mL, 2.5 mmol) was added drop wise which afforded a dark reddish-brown viscous solution. The mixture was stirred at -30 C. for 35 minutes, then a homogeneous THF solution of (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,4-dimethyloxazol-5-yl)methanone (500 mg, 1.05 mmol, in 4 mL THF, Intermediate 51: step b) was introduced at -20 C. The reaction mixture became a dark brown color and was then placed in an ice-water bath and allowed to warm gradually to room temperature. After 45 minutes, the mixture was quenched with aqueous NH4Cl solution and extracted with EtOAc:THF (10:2), 4*50 mL. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to provide a brown oil. Chromatography on silica gel (3% MeOH-DCM increasing to 5% MeOH-DCM) to provide the title compound as a faint amber solid. MS m/e 558.2 [M+H]+. 1H NMR (400 MHz, CDCl3) delta ppm 8.15 (d, J=2.0 Hz, 1H), 7.86 (d, J=8.8 Hz, 1H), 7.54-7.47 (m, 3H), 7.40 (d, J=8.1 Hz, 2H), 7.14 (s, 1H), 4.35 (s, 2H), 4.10 (s, 3H), 4.03 (s, 1H), 3.92 (s, 3H), 2.40 (s, 3H), 1.54 (s, 3H).

According to the analysis of related databases, 16681-65-5, the application of this compound in the production field has become more and more popular.

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