Category: 16681-65-5

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, Safety of 1-Methyl-1H-1,2,3-triazole

Intermediate 18: 1-Methyl-1H-1,2,3-triazole-5-carbaldehydeThe 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, 12.0 mmol) 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 x 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 x 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 title compound as a colorless oil.

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; 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.; WO2015/57206; (2015); 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 16681-65-5 as follows. Quality Control of 1-Methyl-1H-1,2,3-triazole

To a flask containing 1-methyl-1H-1,2,3-triazole (111 mg, 1.34 mmol) was added THF (10 mL) and the solution was cooled to -45 C. using a CH3CN-CO2 bath. n-BuLi (2.5 M in hexanes, 0.5 mL, 1.25 mmol) was added dropwise to provide a white suspension. The suspension was stirred at -45 C. for 25 minutes. A pre-warmed THF solution of (2,4-dichloro-3-(2,2,2-trifluoroethyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (470 mg, 1.17 mmol in 7 mL THF, Intermediate 70) was introduced at -45 C. The reaction temperature was allowed to warm gradually to room temperature over 70 minutes then quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (3*40 mL), and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (2% MeOH-DCM increasing to 8% MeOH) afforded the title compound as a tan amorphous solid. MS (ESI): mass calcd. for C20H17Cl2F3N6O, 484.1. found, 485.0 (M+H)+. 1H NMR (500 MHz, CDCl3) delta ppm 8.60 (s, 1H), 8.44-8.40 (m, 2H), 7.95 (d, J=8.8 Hz, 1H), 7.62 (dd, J=8.8, 1.8 Hz, 2H), 6.95 (s, 1H), 5.89 (s, 1H), 4.05 (q, J=9.6 Hz, 2H), 3.89 (s, 3H), 3.32 (s, 3H).

According to the analysis of related databases, 16681-65-5, the application of this compound in the production field has become more and more popular.

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

Related Products of 16681-65-5, 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

Example 93 (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(3,5-dimethylisoxazol-4-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol To a flask containing 1-methyl-1H-1,2,3-triazole (200 mg, 2.41 mmol) was added THF (17 mL) and the solution was cooled to -43 C. using a CH3CN-CO2 bath. n-BuLi, (2.5 M in hexanes, 0.88 mL, 2.19 mmol) was then added dropwise to provide a white suspension. The suspension was stirred at -40 C. for 20 minutes, then a homogeneous solution of (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(3,5-dimethylisoxazol-4-yl)methanone (500 mg, 1.05 mmol, Intermediate 63: step b) in 2 mL THF was introduced. A dark brownish solution immediately resulted. The reaction mixture was allowed to warm gradually to 0 C. over 25 minutes, then was quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (3*35 mL) and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated to dryness. The residue was purified by FCC (20% EtOAc-hexanes increasing to 50% EtOAc) to provide the title compound as a white solid. 1H NMR (500 MHz, CDCl3) delta 8.08 (d, J=2.1 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.61-7.46 (m, 3H), 7.39 (d, J=8.1 Hz, 2H), 6.94 (s, 1H), 4.81 (s, 1H), 4.32 (s, 2H), 4.09 (s, 3H), 3.98 (s, 3H), 1.95 (s, 3H), 1.82 (s, 3H); MS (ESI): mass calc. for Chemical Formula: C27H23ClF3N5O3; Exact Mass: 557.1. m/z found, 557.9 (M+H).

The synthetic route of 1-Methyl-1H-1,2,3-triazole 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

Synthetic Route of 16681-65-5,Some common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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.

To a stirred solution of 1 -methyl- 1 H- 1,2,3-triazole (0.5 g, 6.0 mmol) in anhydrous tetrahydrofuran (50 mL) at -78 C under an atmosphere of nitrogen was added n-butyllithium (2.5M solution in hexanes, 2.6 mL, 6.6 mmol) dropwise over ten minutes. On complete addition the reaction was allowed to warm to -30 C and stirred for 2 h. A solution of chlorotrimethylstannane (1.3 g, 6.6 mmol) in tetrahydrofuran (2 mL) was added dropwise over 10 minutes then the reaction mixture was allowed to warm to room temperature over 2 h. The reaction was quenched by the addition of saturated ammonium chloride solution (5 mL) then diluted with water (20 mL). The solvent was evaporated in vacuo and the aqueous phase extracted with ethyl acetate (2 x 30 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated to afford a pale yellow oil (1.4 g, 90%). 1H NMR (DMSO- D6,400MHz): 7.61 (s, 1H), 4.04 (s, 3H), 0.40 (s, 9H).

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

Reference:
Patent; GENENTECH, INC.; WO2009/151598; (2009); 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Product Details of 16681-65-5

Intermediate 45: Step a (2,4-Dimethylthiazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol To a flask containing 1-methyl-1H-1,2,3-triazole (1.60 g, 19.3 mmol, Intermediate 42, step a) was added THF (200 mL) and the solution was cooled to -40 C. To this colorless homogeneous solution was added n-BuLi (2.5 M in hexanes, 7.7 mL, 19.2 mmol) dropwise which immediately afforded a dark brown viscous mixture. The mixture was kept between -10 to -20 C. for 60 min, then 2,4-dimethylthiazole-5-carbaldehyde (3.03 g, 21.5 mmol) in THF (5 mL) was introduced and the reaction mixture began to stir much more easily, but still remained brownish. Once the aldehyde was added the reaction was placed in an ice-bath and maintained there until it warmed to room temp. After 3 hours the reaction was quenched by pouring into a saturated solution of NH4Cl at room temperature. The aqueous portion was extracted with EtOAc (5*100 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a brown oil-foam. Flash chromatography on silica gel (10-30% acetone increasing gradient to 10% MeOH-DCM) gave the title compound as a light orange foam.

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; 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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (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.

[00112] 1 -Methyl-1 H-1 ,2,3-triazole (41 mg, 0.495 mmol) was dissolved in THF (4.9 mL) and cooled to -78 C. n-Butyllithium solution in hexanes (240 muIota_, 0.594 mmol) was added dropwise and the solution was stirred for further 5 min before zinc(ll) chloride (3.0 mL, 1 .485 mmol) was added. After 30 min at -78 C, the reaction mixture was diluted with DMF (2.0 mL), tetrakis(triphenylphosphine)palladium(0) (29 mg, 0.025 mmol) and a solution of 4-bromo-2-methoxy-1 -nitrobenzene (1 15 mg, 0.495 mmol) in DMF (500 mu) were added. The solution was stirred at 80 C for 2.5 h. After the mixture was cooled to room temperature, water and EtOAc were added and the phases were separated. The organic phase was washed with water, brine, dried (Na2S04) and the solvent was removed in vacuo. The residue was purified by Biotage silica gel column chromatography eluting with DCM/EtOAc (99/1 to 90/10, 10 g column) to afford the title product as a pale yellow solid (82 mg, 70.7 %). 1 H NMR (500 MHz, CDCI3): <5 4.04 (s, 3H), 4.14 (s, 3H), 7.10-7.13 (m, 2H), 7.82 (s, 1 H), 7.98-8.01 (m, 1 H); LC (Method B)-MS (ESI, m/z) fR 1 .97 min, 235 [(M+H+), 100%]. The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings. Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; NAUD, Sebastien Gaston Andre; BLAGG, Julian; (38 pag.)WO2017/109476; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-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. Recommanded Product: 1-Methyl-1H-1,2,3-triazole

A solution of 1-methyl-1H-1, 2, 3-triazole (3.0 g, 36.1 mmol) in anhydrous THF (100 mL) was cooled to -78 , followed by the addition of butyllithium (15.89 mL, 39.7 mmol) dropwise to give a yellow suspension. The reaction mixture was stirred at -78 for 1 h before N-methoxy-N-methylacetamide (6.52 g, 63.2 mmol) was added. The white suspension was then allowed to warm to 10 and stirred for 16 h. The reaction was quenched with MeOH. This solution was purified by column chromatography on silica gel (petroleum ether /EtOAc 3: 1to 1: 1) to give the product as a solid.1H-NMR: (Chloroform-d400MHz) delta 8.16 (s, 1H) , 4.31 (s, 3H) , 2.58 (s, 3H)

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; ARASAPPAN, Ashok; BUNGARD, Christopher James; FRIE, Jessica L.; HAN, Yongxin; HOYT, Scott B.; MANLEY, Peter J.; MEISSNER, Robert S.; PERKINS, James; SEBHAT, Iyassu K.; WILKENING, Robert R.; (140 pag.)WO2016/29454; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-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. Formula: C3H5N3

A solution of n-BuLi (3.8 mL, 9.5 mmol, 2.5 M solution in hexane) was added slowly to a solution of 1-methyl-1H-1,2,3-triazole (0.83 g, 10 mmol) in THF (48 mL) at -50 C. After addition, stirring was continued for an additional 30 minutes and N-methoxy-N, 2,6-trimethylisonicotinamide (0.97 g, 5.0 mmol, Intermediate 64: step a) dissolved in THF (12 mL) was slowly added. An additional 2 mL of THF was used to complete the quantitative addition. The mixture was stirred at -50 C. for 5 minutes then warmed to room temperature and stirred overnight. The solution was quenched with saturated aqueous NH4Cl. H2O was added and layers were separated. The aqueous layer was extracted with EtOAc and the combined organic extracts washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified using flash column chromatography (0 to 100% EtOAc/DCM) to provide the title compound.

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

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

Reference 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.

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, 12.0 mmol) 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 title compound as a colorless oil.

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; 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.; US2015/105372; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-65-5, These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-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.

A solution of n-BuLi (2.5 M in hexanes, 1.25 mL, 3.12 mmol) was added dropwise by syringe to a solution of 1-methyl-1H-1,2,3-triazole (268 mg, 3.22 mmol) in dry THF (32 mL) in a dry ice-methanol bath. The suspension was stirred for 30 minutes, slowly allowing the reaction mixture to warm to -10 C. (4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (0.500 g, 1.05 mmol, Intermediate 45: step f) in dry THF (5 mL) was added to the mixture via syringe and the resulting mixture was allowed to warm to ambient temperature overnight. The reaction was quenched with water. Brine was added and the aqueous mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-8% MeOH-DCM) to provide the title compound. 1H NMR (500 MHz, CDCl3) delta 8.69 (d, J=1.7 Hz, 1H), 8.24 (d, J=1.9 Hz, 1H), 8.22 (s, 1H), 7.79-7.76 (m, 1H), 7.75 (d, J=8.7 Hz, 1H), 7.57 (d, J=8.1 Hz, 1H), 7.42 (dd, J=8.7, 2.0 Hz, 1H), 6.97 (s, 1H), 5.95 (s, 1H), 4.30 (s, 2H), 4.08 (s, 3H), 3.88 (s, 3H), 3.33 (s, 3H), 2.12 (s, 3H); MS m/e 557.8 [M+H]+.

Statistics shows that 1-Methyl-1H-1,2,3-triazole is playing an increasingly important role. we look forward to future research findings about 16681-65-5.

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