Category: Triazoles

These common heterocyclic compound, 39602-93-2, name is 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, 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. COA of Formula: C3H7IN4

To a preweighed Erlenmeyer flask, 1.1726 grams, 5.18 mmoles of 1-methyl-4-amino-1,2,4-triazolium iodide was dissolved in twenty mL of fresh methanol and stirred vigorously with a Teflon stir bar. Silver nitrate, 0.8805 grams, 5.18 mmoles, was dissolved with 15 ml of methanol along with 3 ml of acetonitrile in a separate flask. The silver nitrate solution was added slowly to the vigorously stirred solution containing the 1-methyl-4-amino-1,2,4-triazolium iodide. After the addition of the silver nitrate solution was completed the reaction mixture was allowed to stir for 45 minutes more, then was filtered through a celite plug into a preweighed flask. The celite plug was washed with three five ml aliquots of fresh methanol. The filtrate flask was evacuated to leave a viscous oil which was then redissolved in 15 ml of fresh methanol and layered with 15 ml of diethyl ether, and subsequently placed in a refrigerator at 4¡ã C. After 24 hours the filtrate solution was decanted away from the precipitated viscous oil, which was washed with three 10 ml aliquots of fresh diethyl ether and vacuum dried to a constant weight, 0.7936 g, 4.92 mmoles of 1-methyl-4-amino-1,2,4-triazolium nitrate. Melting point 54-56¡ã C.; DSC onset 200¡ã C.1H NMR (d6-dmso): 4.051 (singlet); 6.991 (broad singlet); 9.079 (singlet); 10.116 (singlet).13C NMR (d6-dmso): 39.208 (singlet); 143.584 (singlet); 145.615 (singlet).

The synthetic route of 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Drake, Greg W.; Hawkins, Tommy; Tollison, Kerri; US7745635; (2010); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H3N3O2

Example 6 2-{(R)-3-(5?-Chloro-2?-fluorobiphenyl-4-O-2-[(1H-[1,2,3]triazole-4-carbonyl)amino]propyl}-2-methylmalonic Acid [0413] 1H-1,2,3-triazole-4-carboxylic acid (3.3 mg, 29 mumol) and HATU (10.5 mg, 28 mumol) were dissolved in DMF (2.0 mL) and stirred for 15 minutes at room temperature. 2-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]-2-methylmalonic acid (12.0 mg, 32 mumol) and DIPEA (9.2 muL, 53 mumol) were added, and the resulting mixture was stirred for 15 minutes at room temperature, at which time LCMS indicated the mass of the desired compound. The mixture was concentrated in vacuo and the residue was purified by preparative HPLC to yield the title compound (5 mg) as a TFA salt. MS m/z [M+H]+ calc’d for C22H20ClFN4O5, 475.11. found 475.

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

These common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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. Safety of 1H-[1,2,3]Triazole-4-carboxylic acid

Example 15 (R)-5-(5?-Chloro-2?-fluorobiphenyl-4-O-2-hydroxymethyl-2-propyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid (isomers a and b) [0434] (R)-4-Amino-5-(5?-chloro-2?-fluorobiphenyl-4-yl)-2-hydroxymethyl-2-propylpentanoic acid (isomer a; 40 mg, 90 mumol, 1.0 eq.) and DIPEA (40 muL, 228 mumol, 2.5 eq.) were dissolved in DMF (200 muL). 1H-1,2,3-triazole-4-carboxylic acid (17 mg, 150 mumol, 1.5 eq.), HATU (45 mg, 120 mumol, 1.5 eq.), and DIPEA (40 muL, 228 mumol, 2.5 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 until LC/MS analysis revealed consumption of starting material. The mixture was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer a; 15.7 mg). LCMS (ESI): calc. C24H26ClFN4O4=488; obs. M+H=489.2. Retention time: 5.03 min. [0436] (R)-4-Amino-5-(5?-chloro-2?-fluorobiphenyl-4-yl)-2-hydroxymethyl-2-propylpentanoic acid (isomer b; 60 mg, 140 mumol, 1.0 eq.) and DIPEA (40 muL, 228 mumol, 1.6 eq.) were dissolved in DMF (300 muL). 1H-1,2,3-triazole-4-carboxylic acid (24 mg, 210 mumol, 1.5 eq.), HATU (57 mg, 150 mumol, 1.0 eq.), and DIPEA (80 muL, 456 mumol, 3.2 eq.) were dissolved in DMF (900 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), the mixture was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer b; 33.7 mg). LCMS (ESI): calc. C24H26ClFN4O4=488; obs. M+H=489.2. Retention time: 4.98 min. [0437] 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 9.6 minutes, then 100% B for 1.0 minute, detection at 254 nm.

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid 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

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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 16681-70-2, Recommanded Product: 16681-70-2

General procedure: To a stirred solution of 680 mg (1 .78 mmol) (3aR,4S,7R,7aS)-8-{[2-(trifluoro-methyl)phenyl]sulfonyl}octahydro-1H-4,7-epiminoisoindole hydrochloride (1 :1 ) (Intermediate 1) in 10 mL DMF were added 301 mg 1 H-1 ,2,3-triazole-4-carboxylic acid (2.66 mmol, 1 .5 eq), 590 mu 4-methylmorpholine (5.3 mmol, 3 eq) and 1 .01 g HATU (2.66 mmol, 1 .5 eq). After stirring for 16 h at RT, the solution was subjected to preparative HPLC to yield 473 mg (60 %) 1 H-1,2,3-triazol-5-yl[(3aR,4S,7R,7aS)-8-{[2-(trifluoromethyl)phenyl]sulfonyl}octahydro-2H-4,7-epiminoisoindol-2-yl]methanone. LC-MS (Method A1 ): Rt = 0.98 min; MS (ESIpos): m/z = 442 [M+H]+ 1 H NMR (400 MHz, DMSO-d6): delta [ppm] = 1 .40 – 1 .65 (m, 4 H) 2.80 – 3.01 (m, 2 H) 3.1 1 (dd, 1 H) 3.44 (dd, 1 H) 3.93 – 4.10 (m, 1 H) 4.23 (br s, 2 H) 4.39 (br s, 1 H) 7.83 – 7.96 (m, 2 H) 7.98 – 8.07 (m, 1 H) 8.23 – 8.29 (m, 1 H) 8.34 (br s, 1 H) 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 0.851 (1 .86), 1 .154 (4.18), 1 .171 (8.33), 1 .189 (4.15), 1 .232 (5.06), 1 .352 (1 .25), 1 .476 (3.05), 1 .498 (3.54), 1.545 (3.32), 1 .568 (2.64), 1.907 (4.52), 1 .987 (16.00), 2.006 (1.15), 2.332 (1 .00), 2.518 (4.20), 2.523 (3.25), 2.673 (1 .07), 2.686 (1 .44), 2.727 (2.10), 2.869 (1.54), 2.888 (4.37), 2.900 (1.51), 2.919 (1.42), 2.936 (1.81), 2.950 (1.59), 3.079 (1.93), 3.098 (1.95), 3.112 (2.32), 3.133 (1.78), 3.418 (1.78), 3.437 (1.88), 3.450 (2.13), 3.469 (1.64), 3.987 (3.57), 3.999 (1.42), 4.017 (5.50), 4.021 (3.40), 4.034 (3.49), 4.052 (1.15), 4.229 (4.91), 7.884 (3.44), 7.886 (3.44), 7.894 (3.96), 7.901 (8.45), 7.905 (3.69), 7.913 (4.08), 7.918 (4.32), 7.932 (1.44), 7.936 (1.00), 8.004 (4.86), 8.010 (4.74), 8.022 (2.59), 8.027 (3.37), 8.256 (4.32), 8.261 (3.10), 8.274 (4.15), 8.279 (3.47), 8.342 (1.47).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SIEBENEICHER, Holger; STEUBER, Holger; TER LAAK, Antonius; NUBBEMEYER, Reinhard; ROTTMANN, Antje; IRLBACHER, Horst; BADER, Benjamin; PETERS, Michaele; WAGENFELD, Andrea; (110 pag.)WO2018/114677; (2018); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 7343-33-1,Some common heterocyclic compound, 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, molecular formula is C2H2BrN3, 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 the intermediate 5 300 mg, potassium carbonate 133 mg and N,N-dimethylformamide 3 mL was added 3-bromo-1H-1,2,4-triazole 132 mg at 0¡ãC. The mixtures were stirred at 0¡ãC for 2.5 hours and to the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layers were washed with water and brine and dried over anhydrous sodium sulfate. The resulting organic layers were concentrated under reduced pressure. The resulting residues were subjected to a silica gel column chromatography to give the following present compound 3 370 mg. H1-NMR (CDCl3) delta: 9.04 (1H, s), 8.81 (1H, br s), 8.73 (1H, d), 8.35 (1H, br s), 8.26 (1H, d), 3.92 (3H, s), 3.81 (2H, q), 1.39 (3H, t).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1H-1,2,4-triazole, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; TANABE, Takamasa; MIZUNO, Hajime; OKAMOTO, Hiroshi; (41 pag.)US2017/135348; (2017); 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. 107534-96-3, name is 3-((1H-1,2,4-Triazol-1-yl)methyl)-1-(4-chlorophenyl)-4,4-dimethylpentan-3-ol, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C16H22ClN3O

For a 1 :1 co-crystal of tebuconazol and 4-hydroxy benzoic acid, 200,1 mg of tebucona- zol, 80,4 mg of 4-hydroxi benzoic acid and 150 muIota ethanol was grinded in a ball mill (Retsch Modell MM301 ) for 10 minutes by using 20 Hz. The crystalline product gave the PXRD in Figure 3 (table 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 107534-96-3.

Reference:
Patent; BASF SE; SAXELL, Heidi, Emilia; ISRAELS, Rafel; SCHAeFER, Ansgar; BRATZ, Matthias; HOeFFKEN, Hans, Wolfgang; BRODE, Ingo; NAUHA, Elisa; NISSINEN, Maija; WO2011/54741; (2011); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, molecular formula is C9H7N3O, 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. HPLC of Formula: C9H7N3O

Weigh 5.73 g (36 mmol) of 2-methyl-8-hydroxyquinoline, 5.19 g (30 mmol)4-(1-1,2,4-triazolyl)benzaldehyde and 100 mL of acetic anhydride,Add to a 250 mL round bottom flask,The reaction is completely dissolved at room temperature,Move to the magnetic heating mixer.Warming up to 145 C,Heating back,TLC tracking.After 5 hours of reaction,Stop the reaction,Cool and stand still,A large amount of yellow solid precipitated in the reaction solution.Atmospheric pressure filtration,Wash the solid three times,drying,Recrystallization of acetonitrile,Obtained a yellow-brown floc product of 5.31g,Yield 49.71%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27996-86-7, its application will become more common.

Reference:
Patent; Fuyang Normal College; Liu Jie; Miao Hui; Qiao Rui; Liu Zhaodi; (18 pag.)CN109206405; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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. Recommanded Product: 1H-[1,2,3]Triazole-4-carboxylic acid

[0838] lH-1,2,3-triazole-4-carboxylic acid (2.3 mg, 20f.tmol) was combined with HATU (7.7 mg, 20 flillOl) in DMF(2 mL) and stirred at room temperature for 15 minutes. Compound3(7.7 mg, 18 flillOl) andDIPEA(9.6 f.LL, 55 f.tmol)werethen added. The solution was stirred at room temperature for15 minutes, at which time LCMS showed reaction completion.The solvent was removed in vacuo and the crude residuewas dissolved in EtOH (2 mL). A solution of IN LiOH (183f.LL, 183 f.tmol) in water was added, and the resulting solutionwas stirred at room temperature for 30 minutes, at which timeLCMS showed reaction completion. The solvent wasremoved in vacuo and the crude residue was purified byreverse phase chromatography to yield Compound a (3 mg) asa TFA salt. MS m/z [M+Ht calc’d for C23H25ClFN50 4 ,490.16. found 488.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-70-2, its application will become more common.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 67545-00-0, name is 4-Amino-1-methyl-1,2,3-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 67545-00-0, name: 4-Amino-1-methyl-1,2,3-triazole

In a microwave vial (35 mL) was added S-129 (0.78 g, 1.82 mmol), amine 11 (0.18 g, 1.82 mmol), Cs2CO3(1.18 g, 3.64 mmol.) and Dioxane (25 mL). The Argon was purged through septum and the reaction mixture was degassed for about 5 min. To this mixture was added Xantphos (103 mg, 0.2 mmol) followed by Pd2(dba)3(162 mg, 0.2 mmol) and purged with Argon again for 5 min. Vial was sealed with the septum and irradiated at 140 C for 3 h. After filtration, the obtained crude was chromatographed (Biotage, 25 g, eluent: DMC-EtOAc: 10-50%) to afford S-6-1 (390 mg, 44%).1H NMR (400 MHz, DMSO-d6): delta 9.61 (bs, 1H), 7.99 (d, J = 7.8 Hz, 1H), 7.46- 7.10 (m, 10H), 6.87 (d, J = 3.9 Hz, 1H), 5.39 (m, 1H), 4.02 (s, 3H), 3.35- 3.23 (m, 2H), 2.32 (s, 3H), 2.23 (m, 2H). FABMS (M+H) calculated for was 489.1815 found 489.1813. LCMS 99%, tR= 7.37 minutes.

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; SOUTHERN RESEARCH INSTITUTE; AUGELLI-SZAFRAN, Corinne, E.; SUTO, Mark; GALEMMO, Robert; MOUKHA-CHAFIQ, Omar; GUPTA, Vandana; ANANTHAN, Subramaniam; (254 pag.)WO2017/106771; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 41253-21-8, 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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

[Step 1] Synthesis of ethyl 2-methyl-2-(1H-1,2,4-triazol-1-yl)propanoate: At room temperature, cesium carbonate (5.0 g, 15 mmol) and sodium 1,2,4-triazol-1-ide (0.58 g, 6.2 mmol) were added to a solution of ethyl 2-bromo-2-methylpropanoate (1.0 g, 5.1 mmol) in DMF (25 mL). The resulting reaction solution was stirred at 50C for 24 hours, and then concentrated under reduced pressure. Water was added to the obtained crude product, and extraction with chloroform was carried out. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, followed by purifying the obtained crude product by silica gel column chromatography (eluent, hexane:ethyl acetate = 7:3 ? 4:6), to obtain 0.84 g (89%) of ethyl 2-methyl-2-(1H-1,2,4-triazol-1-yl)propanoate (hereinafter referred to as Reference Example Compound 40).

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, Sodium 1,2,4-triazol-1-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Toray Industries, Inc.; NISHIMURA, Yutaka; KATO, Yuko; HAYASHI, Shinnosuke; YAMAZAKI, Aiko; YAMAMOTO, Masashi; ASAOKA, Yoshiji; YAMADA, Masateru; YAMADA, Naohiro; EP2832724; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics