Triazoles

4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, 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. Recommanded Product: 5-Phenyl-1H-1,2,4-triazol-3-amine

General procedure: A mixture of 0.001 mol of enaminone 1, 0.001 mol of the corresponding aminotriazole and 3 ml of dimethylformamide was refluxed for 2 h. The precipitate formed upon cooling of the reaction mixture was filtered off and recrystallized from 3 ml isopropyl alcohol-dimethylformamide mixture (2:1 v/v).

The synthetic route of 4922-98-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ilin, Ivan; Lipets, Elena; Sulimov, Alexey; Kutov, Danil; Shikhaliev, Khidmet; Potapov, Andrey; Krysin, Michael; Zubkov, Fedor; Sapronova, Lyudmila; Ataullakhanov, Fazoyl; Sulimov, Vladimir; Journal of Molecular Graphics and Modelling; vol. 89; (2019); p. 215 – 224;,
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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 4928-87-4

To a reaction of 1/7-1, 2, 4-triazole-3 -carboxylic acid (226 mg, 2.0 mmol) and 2- phenylethanamine (0.27 mL, 2.1 mmol) in dry DMF (10 mL) was added 1- hydroxybenzotriazole monohydrate (337 mg, 2.2 mmol) and EDC (N-(3- Dimethylaminopropyl)-N’-ethylcarbodiimide) (422 mg, 2.2 mmol) followed by N- methylmorpholine (0.88 mL, 8.0 mmol via syringe). The mixture was stirred at room temperature under nitrogen and the solids were gradually dissolved. The contents were stirred at room temperature for 24.0 h, and then slowly diluted into iced water and extracted with DCM (2 x 50 mL). The DCM phase was washed with ice cold water (2 x 100 mL). The DCM phase was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure and chromatographed on silica gel using MeOH and DCM (5:95) as eluents to get the desired amide 20 (189.4 mg, 44 % yield) as a white solid compound. -NMR (400 MHz, DMSO-de): <514.63-14.52 (m, 1H), 8.65-8.25 (m, 2H), 7.33-7.17 (m, 5H), 3.55-3.44 (m, 2H), 2.85 (t, J= 7.6 Hz, 2H,) ppm. MH+ = 217.1 m/z. According to the analysis of related databases, 4928-87-4, the application of this compound in the production field has become more and more popular. Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; NATIONAL JEWISH HEALTH; WEMPE, Michael Fitzpatrick; VAZQUEZ-TORRES, Andres; DAI, Shaodong; (72 pag.)WO2020/41556; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 3641-13-2, 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. 3641-13-2 name is 5-Amino-4H-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.

General procedure: A mixture of benzil (0.01 mol), aldehydes (0.01 mol), 3-amino-1,2,4-triazole-5-carboxylic acid (0.01 mol), ammonium acetate (0.01 mol) and ceric ammonium nitrate (15 mol%) as a catalyst were refluxed in ethanol (15 mL) for about 3-4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was cooled to room temperature. The solid formed was filtered and dried. The crude products were recrystallized by ethanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Nikalje, Anna Pratima G.; Ghodke, Mangesh S.; Kalam Khan, Firoz A.; Sangshetti, Jaiprakash N.; Chinese Chemical Letters; vol. 26; 1; (2015); p. 108 – 112;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4922-98-9, The chemical industry reduces the impact on the environment during synthesis 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, I believe this compound will play a more active role in future production and life.

Example 1; Part A; To the solution of 3-phenyl-1H-1 ,2,4-triazol-5-amine (0.8 g, 5 mmol) in acetic acid (6 mL) was added ethyl 4-chloro-3-oxobutanoate (0.75 mL, 5.5 mmol). The reaction mixture was stirred for 24 hours at 80 0C, and then cooled to room temperature. The reaction mixture was filtered. The precipitates were washed with ACN and dried to give compound 1-1 in a white powder (872 mg, 67percent yield). 1H NMR (400 MHz, CD3OD) delta 8.24-8.18 (m, 2H), 7.54-7.46 (m, 3H), 6.21 (s, 1H), 4.65 (s, 2H).; Example 6; Part A; To the solution of 3-phenyl-1 H-1 ,2,4-triazol-5-amine (0.8 g, 5 mmol) in acetic acid (6 ml_) was added ethyl 4-chloro-3-oxobutanoate (0.75 ml_, 5.5 mmol).The reaction mixture was stirred for 24 hours at 80 0C, and then cooled to room temperature. The reaction mixture was filtered. The precipitates were washed with ACN and dried to give compound 1-1 in a white powder (872 mg,67percent yield). 1H NMR (400 MHz, CD3OD) delta 8.24-8.18 (m, 2H), 7.54-7.46 (m,3H), 6.21 (s, 1 H), 4.65 (s, 2H).; Example 12; Part A; To the solution of 3-phenyl-1 H-1 ,2,4-triazol-5-amine (0.8 g, 5 mmol) in acetic acid (6 mL) was added ethyl 4-chloro-3-oxobutanoate (0.75 mL, 5.5 mmol). The reaction mixture was stirred for 24 hours at 80 0C, and then cooled to room temperature. The reaction mixture was filtered. The precipitates were washed with ACN and dried to give compound 1-1 in a white powder (872 mg, 67percent yield). 1H NMR (400 MHz, CD3OD) delta 8.24-8.18 (m, 2H), 7.54-7.46 (m, 3H), 6.21 (s, 1 H), 4.65 (s, 2H).

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, 5-Phenyl-1H-1,2,4-triazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; SHIPPS, JR., Gerald, W.; CHENG, Cliff, C.; HUANG, Xiaohua; ACHAB, Abdelghani, Abe; ORTH, Peter; VOIGT, Johannes, H.; SOUCY, Kyle, Ann; WO2010/56631; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 74733-90-7, name is 2-(4-Bromophenyl)-2H-1,2,3-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. HPLC of Formula: C8H6BrN3

Step A) 2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2H-1,2,3-triazolePd(dppf)Cl2 (280 mg, 0.343 mmol) was added to a mixture of 2-(4-bromophenyl)-2H-1,2,3-triazole (255 mg, 1.14 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (350 mg, 1.38 mmol), and potassium acetate (340 mg, 3.46 mmol) in 1,4-dioxane (10 mL). The reaction was heated to 80 C. and stirred at this temperature overnight. The reaction was allowed to cool to rt and was diluted with EtOAc (30 mL) and brine (30 mL). The mixture was filtered through celite, and the organic layer was separated from the filtrate. The aqueous layer was extracted with EtOAc (2¡Á30 mL) and the organics were combined, dried (MgSO4), filtered and concentrated. The crude material was purified via flash chromatography using an Analogix SF15-12 g column and an eluent of EtOAc in n-heptane (0-10%) to afford the title compound as an orange solid (240.6 mg, 78.0%). MS (LCMS) m/z 272.4 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.37 (s, 12H) 7.83 (s, 2H) 7.94 (d, 2H) 8.10 (d, J=8.59 Hz, 2H).

The synthetic route of 2-(4-Bromophenyl)-2H-1,2,3-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2012/232083; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27808-16-8, name is 4-Methyl-1H-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 27808-16-8, SDS of cas: 27808-16-8

A mixture of 33(430 mg, 1.00 mmol), 4-methyl-1H-1,2,3-triazole (100 mg,1.20 mmol) and K2CO3 (208 mg, 1.50 mmol) in DMF (4 mL)was stirred at 80C for 2 h. The mixture was quenched withwater at r.t. and extracted with EtOAc. The organic layer wasseparated, washed with water and saturated aqueous NaCl,dried over anhydrous MgSO4 and concentrated in vacuo(508.7 mg). The residue was purified by using preparativeHPLC (column: L-Column2 ODS 20 mm ID¡Á150 mm L;mobile phase A: 0.1% TFA in water; mobile phase B: 0.1%TFA in acetonitrile; flow rate: 20 mL/min). The first elutingfactions (tR1) were concentrated to dryness, and washed withsaturated aqueous NaHCO3, extracted with EtOAc. The organic layer was separated, washed with water and saturatedaqueous NaCl, dried over anhydrous MgSO4 and concentratedin vacuo. The residue (42.7 mg) was crystallized from hexane-ethyl acetate to give 17 (34.4 mg, 0.072 mmol, 7.2%) asa white solid. 1H-NMR (300 MHz, DMSO-d6) delta: 1.04 (3H, s),1.37 (3H, s), 2.44 (3H, s), 4.87 (1H, d, J=8.3 Hz), 5.39 (1H, s),7.23-7.34 (2H, m), 7.48-7.58 (2H, m), 7.93 (1H, d, J=7.5 Hz),8.55 (1H, s), 8.88 (1H, d, J=0.8 Hz), 9.07 (1H, d, J=8.3 Hz),9.50 (1H, d, J=7.5 Hz). MS (ESI/APCI) m/z 476.2 [M+H]+.HPLC purity: 99.4%. mp 260C.

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:
Article; Mikami, Satoshi; Kawasaki, Masanori; Ikeda, Shuhei; Negoro, Nobuyuki; Nakamura, Shinji; Nomura, Izumi; Ashizawa, Tomoko; Kokubo, Hironori; Hoffman, Isaac Dylan; Zou, Hua; Oki, Hideyuki; Uchiyama, Noriko; Hiura, Yuuto; Miyamoto, Maki; Itou, Yuuki; Nakashima, Masato; Iwashita, Hiroki; Taniguchi, Takahiko; Chemical and Pharmaceutical Bulletin; vol. 65; 11; (2017); p. 1058 – 1077;,
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. 135302-13-5, name is 3-Methoxy-4-methyl-1H-1,2,4-triazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Methoxy-4-methyl-1H-1,2,4-triazol-5(4H)-one

EXAMPLE 1 STR24 A mixture of 1.3 g (0.01 mol) of 5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 0.1 g of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1.0 g (0.01 mol) of tertbutyl isocyanate and 50 ml of acetonitrile is stirred for 12 hours at 20 C. and subsequently concentrated under a water pump vacuum. The residue is taken up in methylene chloride, and the mixture is washed with water, dried with magnesium sulphate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is brought to crystallisation by trituration with petroleum ether, and the product is isolated by filtration with suction. 1.4 g (61% Of theory) of 2-tert-butyl-amino-carbonyl-5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 167 C. are obtained.

According to the analysis of related databases, 135302-13-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Aktiengesellschaft; US5356865; (1994); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 7343-33-1, A common heterocyclic compound, 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, molecular formula is C2H2BrN3, 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.

Example 52Preparation of Compound 71 Step A – Synthesis of Compound 52BCompound 52A (1.08 g, 4.8 mmol) was combined with 3-brorno-[1 ,2,4]triazole (0.70 g, 4.7 mmol), trtphenylphosphine (1.49 g, 5.7 mmol) and diisopropyl azodicarboxylate (1.12 mL, 5.7 mmol) in THF (15 mL). The resulting reaction was allowed to stir at room temperature for 18 hours, then the reaction mixture was concentrated in vacuo to provide Compound 52B, which was used without further purification.

The synthetic route of 7343-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; SHAH, Unmesh, G.; BOYLE, Craig, D.; CHACKALAMANNIL, Samuel; NEUSTADT, Bernard, R.; HARRIS, Joel, M.; STAMFORD, Andrew; GREENLEE, William, J.; NEELAMKAVIL, Santhosh, Francis; WO2010/75273; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-Methyl-1H-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 16681-65-5, Recommanded Product: 1-Methyl-1H-1,2,3-triazole

To a flask containing 1-methyl-1H-1,2,3-triazole (200 mg, 2.41 mmol) was added THF (15 mL) and the solution was cooled to -45 C. using a CH3CN-CO2 bath. n-BuLi (2.5 M in hexanes, 1.0 mL, 2.5 mmol) was added dropwise which afforded an opaque white suspension. The mixture was stirred at -45 C. for 25 minutes, then a solution of (4-chloro-3-cyclopentyl-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (475 mg, 1.24 mmol, Intermediate 68: step c) in THF (3 mL) was introduced. After 10 minutes, the -45 C. bath was replaced with an ice-water bath. After 30 minutes, the reaction mixture was quenched with aqueous NH4Cl solution and extracted with EtOAc:THF (2:1, 3*40 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (3% MeOH-DCM increasing to 10% MeOH) provided the title compound as a light tan solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.24 (d, J=1.9 Hz, 1H), 7.69 (d, J=8.7 Hz, 1H), 7.35 (dd, J=8.7, 2.0 Hz, 2H), 7.07 (s, 1H), 6.01 (s, 1H), 4.07 (s, 3H), 3.90-3.80 (m, 4H containing a 3H singlet at 3.86), 3.32 (s, 3H), 2.06-1.94 (m, 3H), 1.94-1.84 (m, 6H), 1.75-1.69 (m, 2H). MS (ESI): mass calcd. for C24H27ClN6O2, 466.2. m/z found 467.1 [M+H]+. The racemate was separated by chiral SFC (Stationary phase: Chiralpak AD-H, 5 mum 250¡Á20 mm, Mobile phase: 70% CO2: 30% EtOH (0.3% iPrNH2)) to give Example 135b as the first compound that eluted from the chiral column and Example 135c as the second compound that eluted from the chiral column.

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; JOHNSON & JOHNSON; 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.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, 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. Formula: C2HBr2N3

General procedure: 3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) or 3-chloro-1,2,4-triazole (300 mg, 2.9 mmol), o-quinone methide precursor 2 (2.9mmol), and K2CO3 (1.2 g, 8.7 mmol) were refluxed for 4 h in DMF (10mL). After completion of the reaction, the mixture was cooled, andpoured into H2O (30 mL). The precipitate formed was collected by filtration,washed with H2O, dried, and recrystallized.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7411-23-6, its application will become more common.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics