Day: May 7, 2021

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. Formula: C3H5N3

A solution of n-BuLi (0.73 mL, 1.8 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 (12 mL) at -50 C. After addition, stirring was continued for an additional 30 minutes and 2-(trifluoromethyl)isonicotinaldehyde (0.350 g, 2.0 mmol) dissolved in THF (4 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 solution. 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 50% EtOAc/DCM) to provide the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-65-5, its application will become more common.

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

Electric Literature of 4928-87-4, 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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

To a reaction of 1/7-1, 2, 4-triazole-3 -carboxylic acid (226 mg, 2.0 mmol) and (R)- l-(4-methoxyphenyl)ethan-l -amine (0.28 mL, 2.1 mmol) in dry DMF (10 mL) was added l-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 h, and then slowly diluted into iced water and extracted with DCM (50 mL x 2). The DCM phase was washed with ice cold water (100 mL x 2). 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 22 (287.1 mg, 58 % yield) as a white solid compound. -NMR (400 MHz, DMSO-de): <514.98-14.44 (m, 1H), 9.16-8.08 (m, 2H), 7.34 (d, J= 8.4 Hz, 2H), 6.88 (d, J= 8.8 Hz, 2H,), 5.18-5.04 (m, 1H), 3.73 (s, 3H), 1.48 (d, J= 7.2 Hz, 3H,) ppm. MH+ = 247.1 m/z. 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, 1,2,4-Triazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see. 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 4928-88-5, 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 4928-88-5 as follows.

Example 5; Scheme 7; Benzoic acid 2-acetoxy-5-(diethoxy- 1-[3-Benzoyloxy-5-(diethoxy-phospriorylmethoxy)- phosphorylmethoxy)-tetrahydro-furan-3-yl ester tpsitrahydro-furan-2-yl]-” * * 1H-[1,2,4]triazole-3-carboxylic acid methyl ester261 5 l-[3-Benzoyloxy-5-(diethoxy-phosphorylmethoxy)-tetrahydro-ftiotaran-2-yl]- UEf-[l,2,4]triazole-3-carboxylic acid methyl ester.; Benzoic acid 2-acetoxy-5-(diethoxy-phosphorylmethoxy)-tetrahydro-furcin-3-yl ester (170 mg, 0.4 mmol), lH-tlA^Triazole-S-carboxylic acid methyl ester (5110 mg, 0.4 mmol) and Bis-(p-nitrophenyl)rhohosphate were reacted according to literature procedure (J. Med. Chem. 2000, 43, 1019-1028). The desired product was isolated in 65percent yield (150 mg). 1H NMR (CDCIa, 300 MHz) delta 8.60 (s, IH), 8.00 (d, 2H, / = 7.8 Hz), 7.60 (t, IH, /= 7.2 Hz), 7.45 (app t, 2H, / = 7.7 Hz), 6.29 (d, IH, /= 1.5 Hz), 5.91-5.98 (m, IH), 5.67-5.71 (m, IH), 4.11-4.23 (m, 4H), 3.96-4.0415 (m, 4H), 3.85-3.92 (m, IH), 2.55-2.72 (m, 2H), 1.29-1.37 (m, 6H). 31P NMR (121.4 MHz, CDCl3) delta 19.8. LRMS (ESI) MH+ C20H27N3O9P requires 484.1 Found 483.8.

According to the analysis of related databases, 4928-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.,; WO2008/5542; (2008); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

626248-56-4, name is 3-(2H-1,2,3-Triazol-2-yl)aniline, 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. Product Details of 626248-56-4

Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (5.00 g, 21.5 mmol) was dissolved in 50 mL DMF. To it were added 3-(2H-l,2,3-triazol-2-yl)aniline (4.13 g, 25.8 mmol) and DIEA (7.50 mL, 43.0 mmol). The mixture was stirred at 40C for overnight. To it was poured 300 mL water. Solid ethyl 4-(3-(2H-l,2,3-triazol-2-yl)phenylamino)-2- (methylthio)pyrimidine-5-carboxylate crashed out. It was collected by filtration, washed with water. The solid was then dissolved in 100 mL dioxane. To it was added LiOH hydrate (2.80 g, 64.5 mmol) and 50 mL water. The mixture was stirred for overnight. To the mixture was added HCl to adjust the pH to 2. Solid carboxylic acid crashed out. It was isolated by filtration, washed with water and dried in vacuum oven. This solid was dissolved in 100 mL DMF. To it were added EDC.HC1 (5.76 g, 30 mmol) and HOBt.H20 (4.60 g, 30 mmol). The mixture was stirred for 2.5 h. To it was added ammonium hydroxide solution (28%, 9.1 mL, 100 mmol). The mixture was stirred for 2 h. To it was poured 300 mL water. Solid 4-(3-(2H- 1,2,3 -triazol-2- yl)phenylamino)-2-(methylthio)pyrimidine-5-carboxamide crashed out. It was collected by filtration, washed with water and dried in vacuum oven (5.77 g). 4-(3-(2H-l ,2,3-Triazol-2-yl)phenylamino)-2-(methylthio)pyrimidine-5-carboxamide (50 mg, 0.15 mmol) was dissolved in 3 mL NMP. To it was added MCPBA (65%, 48 mg, 0.18 mmol). The mixture was stirred for 1.5 h. To it were added DIEA (78 , 0.45 mmol) and tert-butyl (lR,2S)-2-aminocyclohexylcarbamate (64 mg, 0.30 mmol). The mixture was stirred at 90C for 2 h. It was diluted with 100 mL EtOAc, washed with IN NaOH and brine, dried, concentrated in vacuo. The residue was treated with neat TFA at RT for 2 h. It was concentrated and subjected to reverse phase preaparative HPLC to isolate the title compound. MS found for C19H23N90 as (M+H)+ 394.4. UV: lambda=249 nm.

The synthetic route of 626248-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong J.; KANE, Brian; XU, Qing; BAUER, Shawn M.; SONG, Yonghong; PANDEY, Anjali; DICK, Ryan; WO2013/78468; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. Quality Control of 1-Methyl-1H-1,2,3-triazole

Example 25a: (4-chloro-2-ethyl-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol A solution of -butyllithium in hexanes (2.5 M, 0.17 mL, 0.43 mmol) was added dropwise to a stirring solution of 5 -methyl – 1 H- 1 ,2,3-triazole (38,3 mg, 0.461 mmol, prepared according to PCT Int. Appl., 2008098104) in tetrahydrofuran (1.5 mL) at -50 C. After 20 minutes at -50 C, a solution of (4-chloro-2-ethyl-3-(4-(trif]uoromethyl)benzyl)quinolin-6-yl)(imidazol-5-yl)methanone (0, 145 g, 0.307 mmol, Intermediate 25: step b) in tetrahydrofuran (1 .5 mL) was added dropwise. After 5 minutes at -50 C, the flask was allowed to warm to 0 C. After 30 minutes, the mixture was partitioned between half-saturated aqueous sodium chloride solution (25 mL) and ethyl acetate (50 mL). The layers were separated and the organic layer was dried with sodium sulfate. The dried solution was filtered. Silica gel (3 g) was added to the filtrate and the mixture was concentrated by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a silica gel column for flash column chromatography purification. Elution with dichloromethane initially, grading to 10% methanol-dichloromethane provided the title compound as an off-white solid. The solid was further purified by chiral SFC (Chiralpak AD-H, 5 urn, 250 x 20 mm, mobile phase: 75% CO?, 25% ethanol containing 0.03% isopropylamine) to provide two enantiomers. The first eluting enantiomer was Example 25b: NMR (600 MHz, CDC13) delta ppm 8.30 (d, J ~ 2.1 Hz, IH), 8.02 (d, J = 8.8 Hz, IH), 7.57 – 7.49 (m, 3H), 7.21 (d, ./ 7.9 Hz, 21 1 ;¡¤. 7.17 (s, IH), 6.18 (s, IH), 4.91 (s, IH), 4.49 (s, 2H), 3.95 (s, 31 1). 3.40 (s, 3H), 3.00 – 2.90 (m, 2H), 2.30 (s, 3H), 1.35 – 1.28 (m, 31 1): MS (ESI): mass calcd. for C28H26CIF3 6O, 554.2; m z found, 555,2 [M+H]+. and the second eluting enantiomer was Example 25c: H NMR (600 MHz, CDC13) delta ppm 8.32 (d, J = 2.1 Hz, IH), 7.99 (d, J = 8.8 Hz, IH), 7.56 – 7.51 (m, 3H), 7.21 (d, J = 7.9 Hz, 2H), 7.12 (s. IH), 6.14 (s, i l l). 5.83 (s, i l l). 4.48 (s, 2H), 3.93 (s, 3H), 3.38 (s, 3H), 2.98 – 2.90 (m, 2H), 2.24 (s, 3H), 1 ,34 – 1.27 (m, 3H): MS (ESI): mass calcd. for C28C1F3N6Q, 554.2; m/z found, 555.0 [M+Hf.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-65-5, its application will become more common.

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; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 956317-36-5, These common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, 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 round-bottom flask equipped with a magnetic stirrer bar was charged with 5-methyl-2-(2H-1,2,3-triazole-2-yl)benzoic acid (5.0 g, 24.6 mmol, 1.0 equiv) and THF (250 mL). Theresulting solution was cooled to 0 C, followed by successive addition of triethyl amine (3.58 mL, 25.8 mmol, 1.05 equiv) and isobutyl chloroformate (3.35 mL, 25.8 mmol,1.05 equiv). The reaction mixture was stirred at ambient temperature for 1 h. Subsequently, the precipitate was filtered off and the filtrate was concentrated under reduced pressure.The residue was taken up in ethyl acetate and washed with saturated NaHCO3 solution. The organic layer was washed with H20, dried over anhydrous sodium sulfate and concentrated under reduced pressure, yielding (isobutyl carbonic) 5-methyl-2-(2H-1,2,3- triazole-2-yl)benzoic anhydride (6.6 g, 88%) as an orange-brown oil.?H NMR (500 MHz, CDC13) oe = 7.80 (s, 2H), 7.70 (d, J = 8.20 Hz, 1H), 7.64 (d, J = 1.45Hz, 1H), 7.45 (dd, J = 1.45, 8.20 Hz, 1H), 3.98 (d, J = 6.60 Hz, 2H), 2.42 (s, 3H), 1.96(sept, J = 6.71 Hz, 1H), 0.91 (d, J = 6.75 Hz, 6H)?3C NMR (125 MHz, CDC13) oe = 161.0, 148.6, 139.0, 136.4, 135.9, 133.8, 131.2, 124.3, 124.1, 75.4, 27.6, 20.9, 18.7

Statistics shows that 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid is playing an increasingly important role. we look forward to future research findings about 956317-36-5.

Reference:
Patent; SANDOZ AG; HOeFERL-PRANTZ, Kathrin; BARTH, Roland; RICHTER, Frank; ZUPANCIC, Borut; (126 pag.)WO2016/20403; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 107534-96-3, name is 3-((1H-1,2,4-Triazol-1-yl)methyl)-1-(4-chlorophenyl)-4,4-dimethylpentan-3-ol, 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. Safety of 3-((1H-1,2,4-Triazol-1-yl)methyl)-1-(4-chlorophenyl)-4,4-dimethylpentan-3-ol

Complex trans-[PdCl2L2] (I) was prepared at 20by methods A and B at different predetermined Pd(II):L molar ratios. Method A: The batch ratio was Pd(II) : L = 1 : 2.To a magnetically stirred aqueous solution (3 mL) containing K2[PdCl4] (0.30 g, 0.92 mmol), the reagent L (0.57 g, 1.84 mmol) dissolved in acetone (6.5 mL)was added. The brown color of the solution quickly changed to orange. The bulky yellow precipitate was formed in 5 h; in 16 h after the evaporation of acetone,the precipitate was filtered out, washed with water and then hexane, and dried in air. The yield was 97%. Method B: The predetermined ratio was Pd(II) : L =1 : 1. To an aqueous solution (3 mL) containing K2[PdCl4] (0.30 g, 0.92 mmol), the reagent (0.28 g,0.92 mmol) dissolved in acetone (6.5 mL) was added under stirring. A yellow precipitate was formed in few minutes. After stirring for 24 h the precipitate was filtered out, washed with water and hexane, and dried. The yield was 81% based on the reagent.

The synthetic route of 3-((1H-1,2,4-Triazol-1-yl)methyl)-1-(4-chlorophenyl)-4,4-dimethylpentan-3-ol has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khisamutdinov; Shitikova; Anpilogova; Golubyatnikova; Mulagaleev; Murinov; Russian Journal of Inorganic Chemistry; vol. 60; 5; (2015); p. 638 – 646; Zh. Neorg. Khim.; vol. 60; 5; (2015); p. 710 – 718,9;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 27808-16-8,Some common heterocyclic compound, 27808-16-8, name is 4-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.

The 5-chloro-6-methyl-pyrazolo [1,5-a] pyrimidine-3-carboxylic acid ethyl ester (400 mg), 4-methyl -1H-1, 2, 3-triazole (153 mg), potassium carbonate (277 mg) and N, N- dimethyl formamide (5 ml) stirring the mixture at room temperature overnight. The reaction mixture is poured into water at room temperature, the mixture and using ethyl acetate extraction. Organic layer using saturated salt water cleaning, in order to water-free magnesium sulfate drying, and the concentrated under reduced pressure. Aid hemostasis by silica gel column chromatography (ethyl acetate/hexane) purification in order to produce the title compound (106 mg).

The synthetic route of 27808-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKED A PHARMACEUTICAL COMPANY LIMITED; KAWASAKI, MASANORI; MIKAMI, SATOSHI; NAKAMURA, SHINJI; NEGORO, NOBUYUKI; IKEDA, SHUHEI; ASHIZAWA, TOMOKO; MARUI, SHOGO; TANIGUCHI, TAKAHIKO; (135 pag.)TW2016/520; (2016); A;,
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 27996-86-7 as follows. Quality Control of 4-[1,2,4]Triazol-1-yl-benzaldehyde

To a stirred solution of 4-[1,2,4]-triazol-1-yl-benzaldehyde (9.0 g, 52 mmol) in 1,4-dioxane (100 mL), were added K2CO3 (10.76 g, 78 mmol) and methyl triphenyl phosphonium bromide (22.2 g, 62.4 mmol) at room temperature. The resultant reaction mixture was heated to 70 C. for 18 h. After completion of the reaction (TLC), the reaction mixture was cooled to room temperature and filtered and the obtained filtrate was concentrated under reduced pressure. Purification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether) to afforded the title compound as a white solid (5.6 g, 63%): ESIMS m/z 172.09 ([M+H]+).

According to the analysis of related databases, 27996-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171308; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, 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 4928-88-5, Quality Control of Methyl 1H-1,2,4-triazole-3-carboxylate

In a 250 ml of clean three-necked reaction flask provided with a thermometer and mechanical stirrer, add 90 g beta-D-ribofuranose-1,2,3,5-tetraacetate. Oil bath heat until beta-D-ribofuranose-1,2,3,5-tetraacetate is completely melted. Then add 37.8 g 1,2,4-triazolecarboxylic acid methyl ester and 0.6 g bis(4-nitrophenyl)phosphate. Start strirring. At 103 ¡ãC maintain temperature and stir for 10 min. At 108 ¡ãC high vacuum, react for 2h. Cool to 90 ¡ãC, by adding methanol, continue to stir until 50 ¡ãC white crystal the storm analyzes right and left of the, in -15 ¡ã C stirring crystallization 4 hours. Filtering, ice-methanol washing, for 65 ¡ãC drying, (II) 91.2g obtaining white RBV condensates, yield 84.2percent (with four acetylmethylene ribose idea ), (II) the content of the white RBV condensates to 98.1percent, purity of 99.1percent ( unitary method HPLC chromatographic area),

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; Hubei Yitai Pharmaceutical Co., Ltd.; Wu, Xiaoyu; Zou, Zude; Xiong, Zuxiang; Huang, Linjun; Guo, Liangchen; Chen, Jin; (6 pag.)CN105732750; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics