Triazoles

6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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. Computed Properties of C8H8N4

To a solution of Intermediate 19 (95mg, 0.29mmol) in acetic acid (ImI) was added A- triazolylaniline (56mg, 0.35mmol) and the solution was stirred at 8O0C over 2 hours. LCMS analysis showed consumption of starting material.Reaction mixture was cooled and the excess acetic acid removed by evaporation under reduced pressure. The residues were treated with sat. aq. Sodium hydrogen carbonate until cessation of effervescence. The resulting precipitate was filtered and the solids obtained dried under vacuum. Purification by preparative chromatography furnished the desired compound as an off- white solid (33mg, 25%)1H NMR (D6-DMSO) 10.24 (IH, bs), 9.27 (IH, s), 8.82 (IH, s), 8.64 (IH, s), 8.36 (IH, s), 8.24 (IH, s), 8.22 (IH, dd, J 9Hz, 1.75Hz), 8.09 (2H, d, J 9Hz), 7.92 (3H, m), 7.64 (IH, dd, J 8.25Hz, 2Hz), 7.46 (IH, m), 4.87 (IH, quin, J 6Hz), 1.36 (6H, d, J 6Hz) LC-MS rt 2.66 m/z 441 ES+

The synthetic route of 6523-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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: C2H2N3Na

150 g (1 eq) of compound G was added to 1.5 L of DMF and added178 mg (5 eq) of sodium triazole and 38 ml of 1,3-dimethylpropylene urea (DMPU),And the mixture was stirred at 100 to 110 C for 24 hours.The reaction mixture was cooled to room temperature, 1.5 L of water was added to the reaction solution, and impurities were extracted with 400 ml of * 2 DCM. The organic phase was washed with 300 ml of 6NHCl extraction, hydrochloric acid aqueous solution with 100ml * 2DCM washing, separation of hydrochloric acid aqueous solution, temperature control below 30 50% NaOH adjusted PH = 8-9, extracted with 500ml * 2EA, combined EA, 300ml * 5 washing, 300mlBrine, brine, dried over Na2SO4 and concentrated to give a yellow oil. 200 ml of EA was added,Solution, dropping 800ml n-heptane solid wash, stirring at room temperature 3h, suction filtration, 200ml n-heptane washing, wasTo a white solid compound H of 86.9 g, Y = 68.5%, pur = 95.2%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41253-21-8, its application will become more common.

Reference:
Patent; Chongqing Weipeng Pharmaceutical Co., Ltd; Han, Gongchao; Zhou, Zhiliang; Zhou, Xingguo; Xiang, Yong; Xiang, Linling; Gong, Xue; (8 pag.)CN105440022; (2016); A;,
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., Recommanded Product: 1H-[1,2,3]Triazole-4-carboxylic acid

Example 22 1-Acetyl-3-{(R)-3-(5?-chloro-2?-fluorobiphenyl-4-yl)-2-[(3H-[1,2,3]triazole-4-carbonyl)amino]propyl}pyrrolidine-3-carboxylic Acid (isomers a and b) [0464] 1-Acetyl-3-[(R)-2-amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]pyrrolidine-3-carboxylic Acid (isomer a; 10 mg) dissolved in DMF. 1H-1,2,3-triazole-4-carboxylic acid (2 eq.), DIPEA (2 equiv.), and HATU (1 equiv.) were also dissolved in DMF and stirred at room temperature for a few minutes. The solutions were then combined and the resulting mixture stirred at room temperature until the reaction was complete (as seen by LCMS). The mixture was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer a; 4.1 mg). LCMS (ESI): calc. C25H25ClFN5O4=513; obs. M+H=514.3. Retention time: 2.24 min. [0466] 1-Acetyl-3-[(R)-2-amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]pyrrolidine-3-carboxylic Acid (isomer b; (40 mg, 88 mumol, 1.0 eq.) and DIPEA (50 muL, 170 mumol, 2.0 eq.) were dissolved in DMF (0.2 mL). 1H-1,2,3-triazole-4-carboxylic acid (30 mg, 260 mumol, 3.0 eq.), DIPEA (90 muL, 340 mumol, 4.0 eq.) and HATU (65 mg, 170 mumol, 1.9 eq.), were dissolved in DMF (0.6 mL) and stirred at room temperature for 30 minutes. The solutions were then combined and the resulting mixture stirred at room temperature for ten minutes. The mixture was stirred for 20 minutes with an excess of 2N NaOH in MeOH and concentrated to dryness. It was then acidified to pH 3 with HCl and extracted with EtOAc. The organic phase was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer b; 30 mg). LCMS (ESI): calc. C25H25ClFN5O4=513; obs. M+H=514.3. Retention time: 2.24 min. [0467] 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 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; 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, 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic 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. Recommanded Product: 1001401-62-2

To a solution of 2-(2H-1,2,3-triazol-2-yl)benzoic acid (500 mg, 2.65 mmol) in DMF (8 mL) was added HATU (1.51 g, 3.98 mmol) and DIEA (1.03 mg, 7.95 mmol). The resulting mixture was stirred at RT for 30 mins, and then tert-butyl hexahydropyrrolo[3,4-cjpyrrole- 2(1H)-carboxylate (562 mg, 2.65 mmol) was added. The resulting mixture was stirred at RT for2 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (10% – 50% EtOAc in petroleum ether) to give the title compound as a oil. LRMS m/z (M+H) 384.2 found, 384.2 required.

The synthetic route of 2-(2H-1,2,3-Triazol-2-yl)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; LIVERTON, Nigel; REGER, Thomas, S.; SKUDLAREK, Jason, W.; (50 pag.)WO2016/100162; (2016); A2;,
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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H5N3

4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile and 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. A solution of 2,4-difluorobenzonitrile (7.07 g, 50.8 mmol) and 3-methyl-1H-1,2,4-triazole (4.22 g, 50.8 mmol) in N,N-dimethylformamide (45 ml) was treated with powdered anhydrous potassium carbonate (10 g) and the resulting mixture was stirred at 22 C. for 18 h. The solid was then filtered and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The mixture containing the 2 and 4-triazolyl-benzonitriles was purified by a combination of chromatography on silica gel (elution gradient of ethyl acetate in hexane) and on reversed phase silica gel to give 1.86 g (18% yield) of Intermediate 64 and 0.526 g (5% yield) of Intermediate 65. 4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. white crystals (ethyl acetate-hexane); mp 117-118 C. 1HNMR 400 MHz (CDCl3) delta (ppm): 2.54 (3H, s, CH3), 7.24 (1H, m, CH), 7.62 (1H, dd, J=2.5 Hz and J=9.1 Hz, CH), 7.84 (1H, dd, J=5.6 Hz and J=8.6 Hz, CH), 8.82 (1H, s, CH). Anal. Calcd for C10H7FN4: C 59.40, H 3.49, N 27.71; Found: C, 59.25; H, 3.32; N, 27.81. 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. white crystals (ethyl acetate-hexane); mp 120-121 C. 1HNMR 400 MHz (CDCl3) delta (ppm): 2.56 (3H, s, CH3), 7.30 (1H, dd, J=2.5 Hz and J=8.1 Hz, CH), 7.39 (1H, m, CH), 7.91 (1H, dd, J=5.5 Hz and J=8.6 Hz, CH), 8.06 (1H, s, CH). Anal. Calcd for C10H7FN4: C 59.40, H 3.49, N 27.71; Found: C, 59.35; H, 3.70; N, 27.77.

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

Reference:
Patent; Naidu, B. Narasimhulu; US2005/256109; (2005); A1;,
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 1157938-97-0 as follows. category: Triazoles

To a solution of diisoproplylamine (120 g) in dry THF (1500 ml) 1.6 M solution of butyllithium in hexane (730 ml) was slowly added at -40 C. under nitrogen atmosphere. The mixture was allowed to warm up to -20 C. for ca. 10 min, then re-cooled to -78 C. and to this LDA-solution N,N-bis(2,4-dimethoxybenzyl)thiopropionamide (390 g), dissolved in dry THF (500 ml) was slowly added that the reaction temperature did not exceed -40 C. (exothermic reaction, cooling). After addition the mixture was stirred at -40 C. for ca. 1 hr, then at this temperature 1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (223 g), dissolve in dry THF (400 ml), was slowly added, the reaction mixture stirred for another 2 hrs, then within ca. 1 hr warmed up to -20 C. and finally poured on an aqueous phosphate buffer solution (pH 7). The aqueous phase was extracted 3 times with ethylacetate (500 ml) and the combined organic phases dried twice with sodium carbonate, filtered and evaporated under reduced pressure providing 3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)-N,N-bis(2,4-dimethoxybenzyl)thiobutyramide: 590 g (96% yield) as a single diastereomer. This crude material was dissolved at 0 C. under cooling in a mixture of methylenechloride (1000 ml) and triflic acid (150 g) and slowly triethylsilane (500 g) was added within ca. 3 hrs keeping the temperature under 10 C. After the reduction was finished the reaction mixture was poured very slowly on aqueous saturated sodium bicarbonate solution, extracted 3 times with ethylacetate (500 ml), dried with sodium sulphate, filtered and evaporated under reduced pressure providing the crude title compound: 250 g (80% yield). The analytical data were identical with published one for (2R,3R)-enantiomer in U.S. Pat. No. 6,300,353 and WO99/45008.

According to the analysis of related databases, 1157938-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Carbo-Design LLC; US2011/87030; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-70-2,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.

[0713] 3H-1,2,3-triazole-5-carboxylic acid (2.5 mg, 22f.tmol) was combined with HATU (8.4 mg, 22 fllllOl) in DMF(0.3 mL) and stirred for 10 minutes; Et3N (1 eq.) was addedand the mixture was stirred for 1 minute. Compound 2 (22f.tmol) was dissolved in DMF (0.5 mL) and Et3N (3.1 f.LL, 22f.tmol) was added, followed by addition of the activated acidsolution. The mixture was stirred for 30 minutes, concentrated,and purified by preparative HPLC to yield the titlecompound. MS m/z [M + Ht calc’ d for C27H31 ClFN 50 4 , 544.21; found 544.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-[1,2,3]Triazole-4-carboxylic acid, 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

Application of 4928-87-4,Some common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-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.

Example 1: N-[2-[[4-[(lR,3S)-3-[[( lR)-l-(4-Fluoro-3-methoxy-phenyl) ethyl]-amino]cyclopentyl]benzoyl]amino]ethyl]-lH-l,2,4-triazole-3- carboxamide (Compound 101)To a solution of Intermediate 4 (719 mg, 1.8 mmol) in dry DMF (12 mL) was added HOBt (276 mg, 2 mmol) and EDAC (517 mg, 2.7 mmol), and the mixture was stirred at rt for 4 hours. lH-l,2,4-triazole-3-carboxylic acid (200 mg, 1.8 mmol) was then added, and stirring was continued overnight at rt. The solvent was removed under reduced pressure and the crude purified by flash chromatography (30% MeOH/DCM), affording the title compound in 78% yield. *H NMR (300 MHz, DMSO) delta 8.70 (br m, IH), 8.48 (br m, IH), 8.41 (s, IH), 7.76 (d, J = 8.2 Hz, 2H), 7.31 (d, J = 8.2 Hz, 2H), 7.17 (dd, J = 8.6, 1.6 Hz, IH), 7.10 (dd, J = 11.5, 8.3 Hz, IH), 6.89 (ddd, J = 8.1, 4.4, 1.8 Hz, IH), 3.84 (s, 3H), 3.78 (q, J = 6.6 Hz, IH), 3.46 (br m, 4H), 3.04 – 2.85 (m, 2H), 2.15 – 1.54 (m, 6H), 1.43 – 1.19 (m, 4H).

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

Reference:
Patent; LEO PHARMA A/S; MANSSON, Kristoffer; WO2012/69421; (2012); 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. 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9N3O

General procedure: Into a round-bottom flask equipped with a magnetic stirring bar already containing a solution of 10mmolof 1,2,3-triazoles type 12 in 27.5mL of DMSO was added 11mmolof IBX. This mixture was stirred at room temperature for 4h. Next, distilled water (20mL) was added, and stirring was continued for 15minat room temperature. Subsequently, the mixture was filtered, extracted with ethyl acetate and dried over with MgSO4. The product was purified via silica-gel column chromatography using gradient mixture of hexane-ethyl acetate to afford the pure derivatives 11 and 15a-b.

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 103755-58-4.

Reference:
Article; Gonzaga, Daniel; Senger, Mario Roberto; Da Silva, Fernando De Carvalho; Ferreira, Vitor Francisco; Silva Jr., Floriano Paes; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 461 – 476;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-65-5, 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows.

The title compound was prepared according to the patent application WO2008/135826. To a 50 mL 2-necked flask containing 1-methyl-1H-1,2,3-triazole (1.0 g, 12.0 mmol, prepared according to PCT Int. Appl., 2008098104) was added THF (45 mL) and the colorless solution was cooled to -40 C. Then, n-BuLi (2.5 M in hexanes, 4.8 mL) was added dropwise which afforded a dark reddish-brown viscous solution. The mixture was stirred between -30 to -20 C. for 45 minutes, then neat DMF (3 mL, 38.5 mmol) was introduced at -10 C. The mixture was allowed to warm up to room temperature and stirred for 60 minutes, followed by pouring into water. The aqueous portion was extracted with EtOAc (4*50 mL) and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The aqueous portion was back-extracted with DCM (3*50 mL) and dried as above. The combined organics were concentrated to give a light brown oil that was much more UV active than the starting material. TLC in either 25% CH3CN-DCM or 25% EtOAc-DCM showed the product to have a slightly higher Rf than the starting material. Chromatography on silica gel (100% DCM increasing to 25% CH3CN-DCM) provided the titled material as a colorless oil.

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