Category: Triazoles

Synthetic Route of 3641-13-2, 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. 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

3-Nitro-1,2,4-triazole-5-carboxylic acid (HCANT) was made by amodified literature method for conversion of amino-triazoles to thenitro derivative [12]. After addition of NaNO2 (1.10 g, 15.9 mmol) to7 mL of H2SO4 at -5 C, glacial CH3CO2H (15 mL) and finely ground3-amino-1,2,4-triazole-5-carboxylic acid (2.00 g, 15.6 mmol) wereadded. The mixture was then stirred for 10 min to dissolve most ofthe triazole; H2O (25 mL) was then added at a temperature of aroundzero. The resulting yellow solutionwas then added dropwise to a nitritesolution (200 g NaNO2 in 200mL H2O) at 50 C (a rapid addition generatesa hot foam of diazonium salts, with contents erupting from theflask). The green product solution on heating for 2 h at 50 C becomescolourless, and is then extracted with EtOAc (4 ¡Á 50 mL); evaporationof the extracts gives HCANT (1.41 g, 57%). IR: 3416 (N-H, s), 3257(O-H, m), 1710 (C=O, s), 1574 (NO2, m), 1383 (NO2, m), 1268 (m),720 (m). ESI-MS: 159 (M+). Anal. Calcd. for C3H2N4O4: C, 22.78; H,1.28; N, 35.44. Found: C, 22.5; H, 1.4; N, 35.4.

The synthetic route of 5-Amino-4H-1,2,4-triazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kennedy, David C.; James, Brian R.; Inorganic Chemistry Communications; vol. 78; (2017); p. 32 – 36;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 1455-77-2, A common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, 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.

General procedure: To a stirred solution of MMB 14-O-succinate (2, 50 mg, 0.14 mmol) in dichloromethane was added EDC (40.26 mg, 0.21 mmol), HOBt (28.35 mg, 0.21 mmol), triethylamine (42.42 mg, 0.42 mmol) and the appropriate heterocyclic amine (0.14 mmol) at ambient temperature. The reaction mixture was stirred for 3-12 h at ambient temperature. When the reaction was complete (monitored by TLC), water was added and the resulting aqueous mixture was extracted with dichloromethane (2 * 10 mL). The organic layers were combined, washed with water followed by brine solution, and dried over anhydrous Na2SO4. The solvent was then evaporated under reduced pressure to afford the crude product. The crude product was purified by column chromatography (silica gel, 3-5% methanol in dichloromethane) to afford the desired succinamide analog as a white solid.

The synthetic route of 1455-77-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Janganati, Venumadhav; Ponder, Jessica; Thakkar, Shraddha; Jordan, Craig T.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry; vol. 25; 14; (2017); p. 3694 – 3705;,
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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-(2H-1,2,3-Triazol-2-yl)benzoic acid

Step (i): tert-butyl N-{l-methyl-2-[2-(2H-l,2,3-triazol-2- yl)benzamido]cyclopentyl}carbamate To a solution of ieri-butyl N-(2-amino-l-methylcyclopentyl)carbamate (Intermediate 30; 500 mg, 2.333 mmol) in dry DMF (8 ml) was added 2-(2H-l,2,3-triazol-2-yl)benzoic acid (CAS number 1001401-62-2; 485 mg, 2.57 mmol), HATU (1331 mg, 3.50 mmol) and triethylamine (976 mu, 7.00 mmol). The reaction was stirred at room temperature under nitrogen for 17 hours. The reaction was partitioned between ethyl acetate and saturated solution of sodium bicarbonate, washing with brine and dried over magnesium sulfate, filtered and concentrated in vacuo. The crude oil was purified by column chromatography (silica, 0-100% ethyl acetate / petrol) and then by column chromatography (basic silica, 0- 100% ethyl acetate / petrol) to afford the title compound.1H NMR (400 MHz, DMSO-6) delta ppm 1.11 – 1.23 (m, 3 H), 1.37 (s, 9 H), 1.51 – 1.69 (m, 3 H), 1.75 – 1.91 (m, 2 H), 2.00 – 2.06 (m, 1 H), 4.13 – 4.31 (m, 1 H), 6.56 (br. s., 1 H), 7.50 – 7.60 (m, 2 H), 7.60 – 7.69 (m, 1 H), 7.77 – 7.86 (m, 1 H), 8.00 (s, 2 H), 8.48 – 8.67 (m, 1 H)

According to the analysis of related databases, 1001401-62-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, 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. category: Triazoles

To a solution of 135.6 g (1.965 mol) of sodium nitrite in158.2 mL of water at -10 to -5 ¡ãC, we added a solution of 20 g(0.202 mol) of DAT in 423.7 mL 1.2 mol/L sulfuric acid for1.5 h. The reaction mixture was heated up to 60 ¡ãC and stirredfor another 1 h, then cooled the reaction mixture to roomtemperature. 67.2 mL 6 mol/L sulfuric acid and 11.85 g (0.121mol) aminosulfuric acid were added to reaction system andstirred for another 0.5 h, extracted with 322.5 ¡Á 3 mL of trioctylamineand 265.5 mL toluene, dried with magnesiumsulfate overnight. The magnesium sulfate was filtered and thefiltrate reacted with excess ammonia to obtain the yellow solid,dried in vacuum to give 25.1 g of 3,5-dinitro-1,2,4-triazoleammonium (AA DNT).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1455-77-2, its application will become more common.

Reference:
Article; Li, Ya-Nan; Liu, Ning; Su, Peng-Fei; Wang, Ying-Lei; Ge, Zhong-Xue; Li, Hui; Wang, Bo-Zhou; Asian Journal of Chemistry; vol. 26; 21; (2014); p. 7151 – 7156;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 23579-79-5, 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. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

In a 25 mL pressure vial, 3,5-dibromo-1-methyl- 1H-1,2,4-triazole (lnt-41, 424 mg, 1.76 mmol) was dissolved in DMF (5 mL) and potassium carbonate (375 mg, 2.71 mmol), followed by 3- chlorophenol (176 mg, 141 L, 1.36 mmol) were added. The vial was sealed, the reaction mixture was stirred for 15 h at 100 C. After cooling, it was concentrated in vacuo, the residue was purified by column chromatography (silica gel, 70 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 30:70 v/v) to yield the title compound as white solid (388 mg, 99%). 1H NMR (CDCl3, 300 MHz): delta 3.78 (s, 3 H), 7.21-7.28 (m, 2 H), 7.32-7.39 (m, 2 H). MS (ES+) m/z 288.0, 290.0, 292.0 [M+H, Br & CI isotopes] .

The chemical industry reduces the impact on the environment during synthesis 3,5-Dibromo-1-methyl-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

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

7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, 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. name: 3,5-Dibromo-1H-1,2,4-triazole

In a 500 mL round bottomed flask, 3,5-dibromo-1H-1,2,4-triazole (Int-1, 3.00 g, 13.2 mmol) was dissolved in 1,2-dichloroethane (100 mL), and cyclopropylboronic acid (2.84 g, 33.1 mmol), sodium carbonate (3.50 g, 33.1 mmol), copper(II) acetate (2.94 g, 15.9 mmol) and 2,2′- bipyridine (2.50 g, 15.9 mmol) were added. The reaction mixture was stirred for 3 h at 75 C. After that, it was diluted with dichloromethane (100 mL) and washed with saturated aqueous solution of ammonium chloride (100 mL) and brine (100 mL), dried (sodium sulfate) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, 80 g, eluting with dichloromethane / methanol, gradient 100:0 to 95:5 v/v) to afford the title compound as colorless oil (660 mg, 13%). HPLC (method LCMS_fastgradient) tR = 1.00 min. 1H NMR (CDCl3, 300 MHz): delta 1.12- 1.31 (m, 4 H), 3.45-3.54 (m, 1 H). MS (ES+) mJz 265.8, 267.7, 269.8 [M+H, 2 Br isotopes] .

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

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

Synthetic Route of 6523-49-5, 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. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of Intermediate 8 (200 mg) and Intermediate 6 (490 mg) were combined with terakis(triphenylphosphine) palladium (0) (95 mg) in DME (3 ml) and sodium carbonate (1 ml) and heated to 100 overnight. The cooled mixture was diluted with water and extracted into DCM. The organic phases were combined, concentrated and partially purified by column chromatography with CH2Cl2/Et0H/ NH3 (200:8:1) to give coupled material. A portion of this material (70 mg) was heated in acetic acid(1 ml) with 4-triazolylaniline (37 mg) at 80 over 1 h. The mixture was concentrated, basified with sat. NaHCO3 and the resulting precipitate isolated by filtration and washed with water and ether, dried then washed with EtOAc, MeCN, then ether and dried to give the title compound (32 mg, 34 %).1H NMR delta 10.4 (IH, br s), 9.27 (IH, s), 8.82 (IH, s), 8.6 (IH, s), 8.23 (IH, s),8.16 (2H, d, J 8.85Hz), 7.95 (2H, d, J 8.85Hz), 7.44 (2H, m), 7.13 (IH, d, J 8.2Hz), 4.15 (4H, m), 1.37 (6H, m); LC-MS rt 2.44, m/z 453 ES+.

The chemical industry reduces the impact on the environment during synthesis 4-(1,2,4-Triazol-1-yl)aniline. I believe this compound will play a more active role in future production and life.

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

Electric Literature of 288-88-0, 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 288-88-0 as follows.

(1) Sodium hydride (60% dispersion in mineral oil, 13.8 g, 345 mmol) was washed with hexane and suspended in DMF (150 ml). At an ice bath temperature, 1,2,4-triazole (total; 20.7 g, 300 mmol) was added thereto in four divisions. After stirring for 30 minutes, to the mixture was added tritylchloride (total; 83.7 g, 300 mmol) in seven divisions and additionally added DMF (50 ml). After stirring for 1.5 hours at room temperature, to the reaction mixture was added water (600 ml). The precipitated crystal was collected by filteration, washed with water, dissolved in CHCl3 (800 ml) and dried. The solvent was evaporated. The obtained residue was chromatographed on silica gel (ethylacetate:CHCl3=1:2, v/v). The fraction of the objective was concentrated to give 1-trityl-1H-1,2,4-triazole (43.9 g). Yield: 47%.

According to the analysis of related databases, 288-88-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shionogi & Co., Ltd.; US6620841; (2003); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 1455-77-2, 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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

It has been reported that the salts of 1,2,4-triazole and 3-amino-1,2,4-triazole could be obtained via an acid-base neutralization [29, 30]. Likewise, the LiDAtz with two amino groups on the triazole ring was prepared by the neutralization from equimolar 3,5-diamino-1H-1,2,4-triazole (DAtzH) and LiOH. Briefly, equimolar DAtzH and LiOH were added into deionized water separately, mixed and kept reacting and stirring at room temperature for 24 h, and the synthetic process is listed in Scheme 1. The product, a yellow powder, was obtained with 96.8% yield after evaporation of water and then drying at 120 C under vacuum for 24 h. 13C Nuclear magnetic resonance (NMR, 400 MHz, D2O): 161.73 ppm. Fourier transform infrared (FT-IR, KBr, cm-1) spectra: 3374, 3417 (w, nuNH2), 3335 (m, nuH2O), 1608 (m, deltaNH2), 1558 (m, nuC-N), 1475 (s, nuC-N), 1382 (m, nuC-N-C), 1070 (m, nuC-N), 688, 773 (w, deltaN-C-N). Elemental analyses (EA; C2H4N5Li, 105.06): found: C 13.22, H 2.20, N 78.42%; calculated: C 13.20, H 2.22, N 76.96%. High-resolution mass spectra [HRMS-electrospray ionization (ESI)]: m/z: [M+H+] calcd. for C2H5LiN5: 106.0700, found: 106.0700.

The chemical industry reduces the impact on the environment during synthesis 3,5-Diamino-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Fei, Yuqing; Liu, Shimin; Lu, Liujin; He, Yude; Deng, Youquan; Research on Chemical Intermediates; vol. 44; 12; (2018); p. 7187 – 7204;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, 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 C4H7N3

Under the protection of N2, a tetrahydrofuran (5.0 mL) solution of 1,4-dimethyl-1,2,3-triazole (0.56 g, 5.77 mol) was added dropwise to a tetrahydrofuran (5.0 mL) solution of butyllithium (2.77mL, 6.27 mol, 2.4 mol/L n-hexane solution) at -78C, and the resulting mixture was kept at -70C and reacted for 1h. Then chlorotributyltin (1.71 mL, 6.34 mol) was added. The system became clear, and was gradually warmed to room temperature. Water and ethyl acetate were added to the reaction flask, stirred for 15 min, and filtered through Celite filler, and the Celite filler was rinsed with ethyl acetate. After the filtrate was layered, the aqueous phase was extracted with ethyl acetate once. The ethyl acetate phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated to obtain a black residue. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (5:1) to obtain a luminous yellow oily product (1.40g, 63%). 1H NMR (400 MHz, CDCl3) delta 4.03 (s, 3H), 2.35 (s, 3H), 1.45-1.54 (m, 6H), 1.28-1.40 (m, 6H), 1.16-1.21 (m, 6H), 0.91 (t, 9H).

The synthetic route of 60166-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; LI, Jijun; WU, Wei; ZHU, Yan; WANG, Huting; ZHAO, Lijia; HE, Weinan; SUN, Yinghui; PENG, Yong; HAN, Yongxin; (108 pag.)EP3412669; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics