Month: May 2021

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. 288-36-8, name is 1H-1,2,3-Triazole, A new synthetic method of this compound is introduced below., Formula: C2H3N3

To a mixture of 2-bromo-4-fluorobenzoic acid (30 g, 137 mmol), cesium carbonate (89.26 g, 274 mmol) and Cul (5.27 g, 27.4 mmol) in DMF (200 mL) were added N,N’-dimethylcyclohexane-1,2-diamine (3.7 mL,23.3 mmol) and 1H-1,2,3-triazole (18.92 g, 274 mmol). The resulting mixture was stirred at 110C overnight, cooled, concentrated in vacuo and diluted with water (150 mL). The aqueous layer was extracted with EtOAc (300 mL x 3). The aqueous layer was acidified with 2N HCl and extracted with EtOAc (300 mL x 4). The combined organic layers were washed with brine (150 mL x 3), dried over Na2SO4, filtered andthe filtrate concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether : EtOAc = 100: 1 ~ 5 : 1) to provide the title compound as a yellow solid. LRMS m/z (M+H) 208.0 found, 208.0 required.

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; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; BESHORE, Douglas C.; KUDUK, Scott D.; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/18027; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 7343-33-1, 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. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of 3-bromo-1H-1,2,4-triazole (5.0 g, 34 mmol) and cesiumcarbonate (11 g, 34 mmol) in acetonitrile (50 mL) was added 1,1,1-trifluoro-4-iodobutane (6.8 mL, 34 mmol). The solution was stirred at room temperature for 72 hours. The solution was poured into water (50 mL) and extracted with diethyl ether (2 x 100 mL). The combined organic layers were concentrated. Purification by flash column chromatography using 0-20percent ethyl acetate/hexanes as eluent, provided the titlecompound as a 70:30 mixture of isomers (3.2 g, 37percent). The mixture was used in the next step without further purification: 1H NMR (400 MHz, CDCI3) O 7.96 (s, 1H), 4.22 (t, J = 6.5 Hz, 2H), 2.27 ? 2.07 (m, 4H); 19 NMR (376 MHz, CDCI3) O -65.83.

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-Bromo-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOW AGROSCIENCES LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; SPARKS, Thomas C.; (131 pag.)WO2017/40060; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, 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: Methyl 1H-1,2,4-triazole-3-carboxylate

EXAMPLE 1 A mixture of methyl 1,2,4-triazole-3-carboxylate (26.4 g, 0.21 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (60.2 g, 0.19 mole) was melted and then 1.1 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 6 hours, while maintaining the temperature of the reaction mixture at 85+-5° C. And then, the reaction mixture was crystallized with 300.8 ml of methanol to give 57.9 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 78.9percent). NMR (CDCl3) delta (ppm): 2.12(t, 9H), 3.99(s, 3H), 4.25(m, 1H), 4.48(m, 2H), 5.57(t, 1H), 5.76(q, 1H), 6.07(d, 1H), 8.44(s, 1H)

The synthetic route of 4928-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 74733-90-7, name is 2-(4-Bromophenyl)-2H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

Step 5. 2-(4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)-2H-1 ,2,3- triazole. [1.1.5d] A microwave vial was charged with 1.1.5c (1.66 g, 7.41 mmol) and 1 ,4-dioxane (60 mL). KOAc (2.254 g, 22.97 mmol) and bis(pinacolato)diboron (2.258 g, 8.89 mmol) were added and the mixture was purged with N2 for 5 minutes. PdCI2(dppf).CH2CI2 adduct (0.605 g, 0.741 mmol) was then added and the reaction mixture was stirred at 68 C for 5 hours. The mixture was diluted with EtOAc and stirred with Siliabond DMT overnight, then washed with water, brine, dried filtered and evaporated onto silica gel. Purification by flash column chromatography on silica gel (EtO Ac/Heptane, 0 to 40%) afforded product 1.1.5d (1.38 g, 68.7 % yield) as an off white solid. LCMS (m/z) 272.2 [M+H]+ 1H NMR (400 MHz, CDCI3) delta 8.10 (d, J = 8.61 Hz, 2H), 7.94 (d, J = 8.22 Hz, 2H), 7.81 – 7.86 (m, 2H), 1.34 – 1.42 (m, 12H)

The synthetic route of 74733-90-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FU, Jiping; KARUR, Subramanian; MADERA, Ann Marie; PECCHI, Sabina; SWEENEY, Zachary Kevin; TJANDRA, Meiliana; YIFRU, Aregahegn; WO2014/160649; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-65-5, A common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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 solutionofn-butyllithiuminhexanes(2.5 M, 0.32 mE, 0.81 mmol) was added dropwise to a stirring solution of i-methyl-1H-i,2,3-triazole (70.4 mg, 0.848 mmol, prepared according to PCT Int. Appl., 2008098104) in tetrahydrofuran (1 mE) at -50C. After 20 minutes, a solution (gently warmed with a heat gun to dissolve the ketone starting material) of (3-(4-(1H-pyrazol-i -yl)benzyl)-4-chloro-2-methoxyquino- lin-6-yl)(i ,2-dimethyl- 1H-imidazol-5-yl)methanone (200 mg, 0.42 mmol, Intermediate 21: step b) in tetrahydroffiran (1 mE) was added dropwise. After 5 minutes, the flask was allowed to warm to 23C. After 20 minutes, water (1 mE) was added. The biphasic mixture was partitioned between saturated aqueous sodium chloride solution (25 mE) and ethyl acetate (50 mE). The layers were separated and the organic layer was dried with sodium sulfate. The dried solution was filtered. Silica gel (2 g) was added to the filtrate and the mixture was concentrated by rotary evaporation to afford a free-flowing powdet The powder was loaded onto a silica gel colunm for flash column chromatography purification. Elution with dichloromethane initially, grading to 10% methanol-dichloromethane provided the title compound which was further purified by RP-HPEC eluting initially with 5% acetonitrile-water (containing 0.05% trifluoroacetic acid), grading to 95% acetonitrile-water (containing 0.05% trifluoroacetic acid) to provide the title compound as a white solid after partitioning the purified material between dichloromethanesaturated aqueous sodium bicarbonate solution, separating the layers, drying the organic layer with sodium sulfate, filtering the dried solution, and concentrating the filtrate to dryness. ?H NMR (400 MHz, CDC13) oe ppm 8.21 (s, 1H), 7.85 (d, J=2.4 Hz, 1H), 7.74 (d, J=8.8 Hz, 1H), 7.67 (d, J=i.7 Hz, 1H), 7.60-7.53 (m, 2H), 7.41-7.33 (m, 3H), 7.11 (d, J=i .4 Hz, 1H), 6.46-6.39 (m, 1H), 6.08-6.02 (m, 1H), 4.27 (s, 2H), 4.08 (s, 3H), 3.89 (s, 3H), 3.35 (s, 3H), 2.20 (s, 3H); MS (ESI):mass calcd. for C29H27C1N802, 554.2. mlz found, 555.2 [M+H].j0650] (3-(4-(i H-Pyrazol- 1 -yl)benzyl)-4-chloro-2-meth- oxyquinolin-6-yl)(i ,2-dimethyl-i H-imidazol-5-yl)(i -methyl-1H-i,2,3-triazol-5-yl)methanol was purified by chiral SFC (Chiralpak AD-H, 5 pm, 250×20 mm, mobile phase:55% C02, 45% methanol containing 0.03% isopropylamine) to provide two enantiomers. The first eluting enantiomer was Example 19b: ?H NMR (500 MHz, CDC13) oe ppm 8.17 (d, J=2.2 Hz, 1H), 7.88-7.84 (m, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.70-7.66 (m, 1H), 7.61-7.55 (m, 2H), 7.41-7.34 (m, 3H),7.18 (s, 1H), 6.47-6.39 (m, 1H), 6.16 (s, 1H), 4.32 (s, 2H),4.10 (s, 3H), 3.92 (s, 3H), 3.40 (s, 3H), 2.33 (s, 3H); MS (ESI):mass calcd. for C29H27C1N802, 554.2. mlz found, 555.5 [M+H] + and the second eluting enantiomer was Example 1 9c:?H NMR (500 MHz, CDC13) oe ppm 8.18 (d, J=2.2 Hz, 1H), 7.85 (d, J=2.5 Hz, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.68 (d, J=1.7 Hz, 1H), 7.61-7.55 (m, 2H), 7.42-7.34 (m, 3H), 7.17 (s, 1H), 6.43 (t, J=2.i Hz, 1H), 6.13 (s, 1H), 4.31 (s, 2H), 4.10 (s, 3H),3.91 (s, 3H), 3.39 (s, 3H), 2.31 (s, 3H)

The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings.

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.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application 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.

The molar ratio of 9,10-dibromoanthracene: 1H-1,2,4-triazole: potassium carbonate: copper oxide is 2: 10-15: 30: 1In the magnet,A 50 mL three-necked round bottom flask equipped with a reflux condenser and a thermometer was charged with CuO (0.0398 mg, 0.5 mmol)Potassium carbonate (2.0731 g, 15 mmol),Triazole (0.345 mg, 5 mmol),9,10-dibromoanthracene (0.3360 g, 1 mmol),20 mL DMF.Start stirring at 100 oC,Reaction for 24 hours.After the reaction,The reaction solution was cooled to room temperature,Filtration, the filtrate was added 100 mL of water,Precipitation precipitation, filtration,The filter cake was collected in a yield of 60%.

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, its application will become more common.

Reference:
Patent; Tianjin Normal University; Wang Zhongliang; Yang Xi; Guo Changcheng; Shang Yuntao; Zhang Zhigang; Wang Ying; (11 pag.)CN106188104; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Methyl-1H-1,2,4-triazole

A mixture of 3-methyl-lH-l,2,4-triazole (15.0 g, 181 mmol), l,2-difluoro-4-nitrobenzene (28.7 g, 181 mmol), and sodium bicarbonate (15.2 g, 181 mmol) in DMSO (100 mL) was heated at 80 C for 48 h. The reaction mixture was allowed to cool to rt and was poured into water (800 mL). The aqueous mixture was extracted with EtOAc (3 x 200 mL). The combined organic extracts were sequentially washed with water (500 mL) and brine solution (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude reaction mixture was purified using silica gel chromatography (30-80% EtOAc/hexane, linear gradient) to afford two regioisomeric products. Pure fractions of the less polar regioisomer were combined and concentrated to afford l-(2-fluoro-4-nitrophenyl)-3-methyl-lH-l,2,4-triazole (7.2 g, 30.8 mmol, 17 % yield) as an off-white solid. Data for l-(2-fluoro-4-nitrophenyl)-3-methyl-lH-l,2,4- triazole [Bl]: LC-MS (M+H)+ = 223.1. XH NMR (500 MHz, CDC13) delta ppm 8.73 (d, J=2.7 Hz,l H), 8.15 – 8.26 (m, 3 H), 2.53 (s, 3 H). Pure fractions of the more polar regioisomer were combined and concentrated to afford l-(2-fluoro-4-nitrophenyl)-5- methyl-lH-l,2,4-triazole (6.23 g, 15 % yield) as an off-white solid. Data for l-(2-fluoro- 4-nitrophenyl)-5-methyl-lH-l,2,4-triazole [CI]: LC-MS (M+H)+ = 223.1. ‘H NMR (500 MHz, CDC13) delta ppm 8.18 – 8.24 (m, 2 H), 8.04 (s, 1 H), 7.69 – 7.78 (m, 1 H), 2.47- 2.53 (m, 3 H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; THOMPSON III, Lorin A.; WU, Yong-Jin; ZHANG, Yunhui; WO2012/9309; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 41253-21-8, 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. 41253-21-8 name is Sodium 1,2,4-triazol-1-ide, 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.

(2) Prepare a thermometer, a condenser,Add 250 ml of DMF and 1,2,4-triazole sodium salt (18.5 g 203 mmol) to a 250 ml four-neck reaction flask of a stirrer.Add 1-chloro-2-(4-chlorophenyl)-3-cyclopropylbutan-2-ol (44 g, 170 mmol),Heat to 100 C, reaction 60 ~ 100min, sample analysis,When the content of 1-chloro-2-(4-chlorophenyl)-3-cyclopropylbutan-2-ol is less than 1%,It is considered as the end of the reaction. Cool to room temperature,The reaction droplets were added to 120 ml of cold water.The precipitated solid was stirred, filtered, washed with water, dried.A cyproconazole having a content of 96% was obtained in a weight yield of 90%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Sodium 1,2,4-triazol-1-ide, and friends who are interested can also refer to it.

Reference:
Patent; Huai’an Guorui Chemical Co., Ltd.; Zhang Pu; Li Ming; Jin Yucun; Chen Chao; Zhong Yu; Chen Mingguang; Wang Fengyun; (8 pag.)CN109400542; (2019); A;,
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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1H-[1,2,3]Triazole-4-carboxylic acid

(R)-4-Amino-2-(2-azidoethyl)-5-(5?-chloro-2?-fluorobiphenyl-4-yl)-2-hydroxymethylpentanoic acid (9 mg, 21 mumol, 1.0 eq.) and DIPEA (15 muL, 86 mumol, 4.0 eq.) were dissolved in DMF (0.2 mL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 80 mumol, 4 eq.) and DIPEA (30 muL, 172 mumol, 8.1 eq.) were dissolved in DMF (0.5 mL). The solutions were then combined and the resulting mixture stirred at room temperature for 20 minutes; LC/MS analysis revealed a mixture of mono- and bis-acylated products. The mixture was concentrated to an oil and dissolved in a mixture of 2N NaOH (2 mL) and MeOH (1 mL) and stirred for 30 minutes at 60 C.; when the reaction was complete (as determined by LC/MS analysis), the mixture was concentrated in vacuo and acidified to pH 3 with aqueous HCl, and extracted with EtOAc. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to yield crude Compound 1 (10 mg). LCMS (ESI): calc. C23H22ClFN2O4=515; obs. M+H=516.2. Retention time: 4.93 min.

According to the analysis of related databases, 16681-70-2, the application of this compound in the production field has become more and more popular.

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 584-13-4,Some common heterocyclic compound, 584-13-4, name is 4H-1,2,4-Triazol-4-amine, molecular formula is C2H4N4, 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: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), iodoalkene (1-4) or iodoarene (5-19) (1mmol) were dissolved in DMF (10mL) under argon in a three-necked flask equipped with a reflux condenser and a balloon on the top. Aminotriazole nucleophile (a, b or c) (1.2mmol) and triethylamine (0.5mL) were added. The atmosphere was changed to carbon monoxide. (Caution: High pressure carbon monoxide should only be used with adequate ventilation (hood) using CO sensors as well.) The reaction was conducted for the given reaction time upon stirring at 70C. The mixture was then concentrated and evaporated to dryness. Toluene (15mL) was added to the residue, the precipitate (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.

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

Reference:
Article; Gergely, Mate; Boros, Borbala; Kollar, Laszlo; Tetrahedron; vol. 73; 48; (2017); p. 6736 – 6741;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics