Day: May 25, 2021

Synthetic Route of 16681-65-5, 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. 16681-65-5 name is 1-Methyl-1H-1,2,3-triazole, 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.

Example 57 Cis-(1S)-N-methyl-7-(5-(N(1)methyl-1,2,3-triazolyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine To a solution of N(1)-methyl-1,2,3-triazole (Prepared by the general method described in J. Chem. Soc., Perkin Trans. I, 1973, 2506) (0.115g, 0.00139mol) in tetrahydrofuran (2ml) at -78C under nitrogen was added n-butyllithium (2.5M solution in hexane) (0.00139mol) and after 15 minutes, zinc chloride (0.00139mol) (0.5M solution in tetrahydrofuran). The reaction was warmed to 0C and tetrakis(triphenylphosphine)palladium (0.053g) and a solution of the iodide product of Example 1(a) (0.2g, 0.00046mol) in tetrahydrofuran (5ml) added and the reaction heated at reflux for 16 hours. The reaction was cooled to room temperature, saturated aqueous ethyldiamine tetra-acetic acid di-sodium salt solution was added, the mixture stirred for 30 minutes, water was added and the mixture extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium bicarbonate, brine and dried (MgSO4). The solution was filtered and the solvent removed under reduced pressure. The crude product was purified on silica gel eluding with 100: 2.5: 1 dichloromethane: methanol: 0.88 ammonia to give the title compound as a pale yellow foam (0.148g, 83%). MS m/z 387 (MH)+ 1H-NMR (CDCl3): delta = 1.90 (1H, m), 2.05 (3H, m), 2.55 (3H, s), 3.77 (1H, t), 4.04 (1H, t), 4.10 (3H, s), 6.93 (1H, dd), 7.00 (1H, dd), 7.16 (1H, dd), 7.26 (1H, s), 7.38 (1H, dd), 7.46 (1H, s), 7.70 (1H, s).

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

Reference:
Patent; Pfizer Limited; PFIZER INC.; EP1157002; (2005); B1;,
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 7411-23-6 as follows. Quality Control of 3,5-Dibromo-1H-1,2,4-triazole

To a solution of 3,5-dibromo-1H-1,2,4-triazole (Int-1, 5.0 g, 22.0 mmol) in DMF (70 mL) was added sodium hydride (793 mg, 33.1 mmol) at 0C under argon atmosphere. After complete addition reaction was allowed to stir at 25C for 30 min. Then 2-iodopropane (2.6 mL, 26.4 mmol) was added followed by stirring at 40C for 4 h. After complete consumption of starting material (as monitored by TLC) reaction mixture was poured into ice-water followed by extraction with MTBE. The organic layer was separated and dried over sodium sulphate. Solvent was evaporated under reduced pressure to afford the title compound as yellow liquid (5.4 g, crude) which was sufficiently pure for use in next step. 1H NMR (DMSO-d6, 400 MHz): 1.39 (d, J = 6.6 Hz, 6 H), 4.64-4.71 (m, 1 H). MS (ES+) m/z 270.0 [M+H].

According to the analysis of related databases, 7411-23-6, the application of this compound in the production field has become more and more popular.

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

Adding a certain compound to certain chemical reactions, such as: 7170-01-6, name is 3-Methyl-1H-1,2,4-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 7170-01-6, Formula: C3H5N3

Intermediate 596-(5-Methyl-1 H-1 ,2,3,4-tetrazoH -yl)pyridine-3-carboxylic acid To a solution of methyl 6-aminopyhdine-3-carboxylate (1 .52 g) in dichloromethane (10 mL) and pyridine (3 mL) is added acetic anhydride (2 g) and the solution is stirred at r.t. overnight. After concentration water and dichloromethane are added and the organic layer is separated, washed with saturated aqueous CuSO4, then water, dried over MgSO4 and concentrated. The N-acyl compound is dissolved in MeCN (20 mL) and sodium azide (4 g) and SiCI4 (4 mL) are added and the mixture is stirred at r.t. overnight. The reaction is quenched by slow addition to an ice/NaHCO3 mixture and extracted with ethyl acetate. The organic extracts are dried over MgSO4 and concentrated. The crude ester is dissolved in MeOH (30 mL) and 4 M NaOH (3 mL) is added and stirred at r.t. for 2 h. The mixture is neutralized to pH 7 with 6 M HCI, concentrated and then acidified with 6 M HCI and the precipitate is filtered off washing with water and dried by suction to give the title compound. LC (method 20): tR = 1 .52 min; Mass spectrum (APCI): m/z = 206 [M+H]+.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/168315; (2012); A1;,
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. 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