Triazoles

Related Products of 7411-23-6, These common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-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.

A solution of 3,5-dibromo-1H-1,2,4-triazole (250 mg, 1.1 mmol), 2-bromoethyl methyl ether (0.17 mL, 2.2 mmol) and triethylamine (0.46 mL, 3.3 mmol) in DMA (5 mL) was stirred at 55 C for 18 h. The reaction mixture was filtered and the solvent removed in vacuo. The product was purified via silica column chromatography eluting with 0-100% EtOAc in Pet. Ether to yield 3,5-dibromo-1-(2-methoxyethyl)-1,2,4-triazole (260 mg, 0.91 mmol, 83% yield) as a colourless oil. UPLC-MS (ES+, Method A), 1.34 min, m/z 285.9 [M+H]+.

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 138624-97-2, 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. 138624-97-2 name is 1-Benzyl-1H-1,2,4-triazole-3-carboxylic acid, 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 (3R)-3-amino- 1, 8-dimethyl-4,5-dihydro-3H-pyrido [3,4-b] azepine-2,7-dione (15 mg, 0.07 mmol), 1-hydroxybenzotriazole (11 mg, 0.08 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (16 mg, 0.08 mmol) and 1 -benzyl1,2,4-triazole-3-carboxylic acid (17 mg, 0.08 mmol) in N,N-dimethylformamide (3 mL) was stirred at 25 C for 2 h. The mixture was concentrated under reduced pressure and the residue was purified by RP-HPLC (acetonitrile 20-50% / 0.05% ammonium hydroxide in water)afford arbitrarily assigned (R)- 1 -benzyl-N-( 1, 8-dimethyl-2,7-dioxo-2,3 ,4,5 ,7 ,8-hexahydro-1 H-pyrido [3,4-b] azepin-3-yl)- 1 H-i ,2,4-triazole-3-carboxamide (21.2 mg, 76%) as a white solid. ?H NMR (400 MHz, CD3OD) 8.56 (s, 1H), 7.87 (s, 1H), 7.37 – 7.33 (m, 5H), 6.49 (s, 1H), 5.47 (s, 2H), 4.71 – 4.65 (m, 1H), 3.59 (s, 3H), 3.33 (s, 3H), 2.74 – 2.69 (m, 2H), 2.45 – 2.38 (m, 1H), 2.13 – 2.08 (m, 1H). LCMS RT = 0.702mi m/z = 407.1 [M + H]. LCMS (5 to 95% acetonitrile in water + 0.1% formic acid over1.5 mins) retention time 0.702 mi ESI+ found [M+H] = 407.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Benzyl-1H-1,2,4-triazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; (105 pag.)WO2018/73193; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 27808-16-8,Some common heterocyclic compound, 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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-bromo-6-methylpyridine-2-carboxylic acid (408 mg, 1 .89 mmol) was dissolved in a mixture of 1 ,4-Dioxane (2ml_)Water (0.200ml_), then 4-Methyl-1 H-1 ,2,3-triazole (236 mg, 2.84 mmol), cesium carbonate (1 .24 g, 3.78 mmol), Cul (18 mg, 0.09 mmol) and (1 R,2R)-N 1 , N2-dimethylcyclohexane-1 ,2-diamine (54 mg, 0.38 mmol) were added. The mixture was stirred at 120 C for 2 hrs. Reaction mixture was cooled to RT and then water and MTBE were added. After vigorously stirring, the layers were separated and the aqueous one was acidified to pH 2 with HCI 6N. The acidic solution was concentrated and purified by RP on C18 column [eluting H20 (0.1 % HCOOH)/CH3CN from 100:0 to 60:40] affording 6-methyl-3-(4-methyl-2H-1 ,2,3-triazol-2-yl)pyridine-2-carboxylic acid (p95, 274 mg, y= 66% yield) and 6-methyl-3-(4-methyl-1 H-1 ,2,3-triazol-1 -yl)pyridine-2- carboxylic acid (p96, 40 mg, y=10%) as a white solids. P95 MS (/77/z): 219.2 [MH]+ 1 H NMR (MeOD-d4) delta 8.17 (d, 1 H), 7.72 (s, 1 H), 7.54 (br. s., 1 H), 2.62 (br. s., 3 H), 2.38 (s, 3 H) P96 MS (mlz): 219.2 [MH]+ 1 H NMR (MeOD-d4) delta 8.05 (s, 1 H), 7.94 (d, 1 H), 7.62 (d, 1 H), 2.67 (s, 3 H), 2.40 (s, 3 H)

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

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application 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.

A solution of 2-iodobenzoic acid (3.0 g, 12.09 mmol) in DMF (1.0 mL) was treated with 1,2,3-triazole (1.5 g, 21.7 mmol), copper(I) iodide (0.25 g, 1.2 mmol), Cs2CO3 (7.08 g, 21.7 mmol), and trans-N,N?-dimethylcyclohexane-l ,2-diamine (0.31 g, 2.17 mmol). The mixture was heated at 120 CC for 12h. The reaction was cooled to ii, diluted with EtOAc, and filtered through Celite. The residue was purified by gradient elution on Si02 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the title compound.?HNMR (500 MHz, DMSO-d6) 3 13.05 (br s, 1H), 8.12 (s, 2H), 7.81-7.52 (m, 4H) ppm. LRMS m/z (M+H) 190.2 found, 190.2.

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; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (97 pag.)WO2016/100157; (2016); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7411-23-6, A common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, 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 colorless solution of 3,5-dibromo-lH-l,2,4-triazole (lnt-1, 250 mg, 1.1 mmol, Eq: 1) and bromocyclobutane (179 mg, 1.32 mmol) in DMF (3 ml) was added K2CO3 (305 mg, 2.2 mmol). The vial was closed under argon and stirred over night at 120C. The reaction mixture was diluted with 25 mL H20 and extracted with EtOAc (2 x 25 mL). The organic layers were washed with sat NaCl (3 x 25 mL), dried over MgS04 and concentrated in vacuo. The title compound was isolated as a yellow liquid (288 mg, 93 % yield). MS (ES+) m/z: 281.9 [(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; 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

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