Month: May 2021

Synthetic Route of 103755-58-4, 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. 103755-58-4 name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, 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.

(1-Phenyl-1H-1,2,3-triazol-4-yl)methanol (0.37 g, 2.0 mmol) was added at 0 C to a mixture of potassium hydroxide (0.64 g, 5.0 mmol) and p-toluenesulfonyl chloride (0.45 g, 2.2 mmol) in tetrahydrofuran (8 mL). The mixture was stirred at room temperature for 3 h. The mixture was then diluted with ethyl acetate (20 mL) and washed with water (2 x 20 mL). The organic layer was dried over with MgSO4, concentrated in vacuo and the obtained crude product was purified by column chromatography (ethyl acetate/hexanes, 3:7) on a silica gel to give compound 2 (0.33 g, 50%) as a white solid; m.p. 104-106 oC. 1H NMR (300 MHz, CDCl3): delta = 8.00 (s, 1 H), 7.82 (d, J = 8.3 Hz, 2 H), 7.69-7.65 (m, 2 H), 7.56-7.43 (m, 3 H), 7.34 (d, J = 8.0 Hz, 2 H), 5.30 (d, J = 0.3 Hz, 2 H), 2.43 (s, 3 H). 13C NMR (75 MHz, CDCl3): delta = 145.3, 141.8, 136.8, 133.1, 130.1, 130.0, 129.3, 128.1, 122.3, 120.7, 63.2, 21.7. HRMS (ESI): calcd. for C16H16N3O3S [M + H]+ 330.0912; found 330.0913.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Kwon, Young-Do; Son, Jeongmin; Yun, Mijin; Chun, Joong-Hyun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2848 – 2852;,
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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., SDS of cas: 4928-87-4

To a reaction of 1/7-1, 2, 4-triazole-3 -carboxylic acid (100 mg, 0.87 mmol) and 4- Methoxy-3- (trifluoromethyl)benzylamine (200 mg, 0.97 mmol) in dry DMF (10 mL) was added 1- hydroxybenzotriazole monohydrate (146 mg, 0.97 mmol) and EDC (N-(3- Dimethylaminopropyl)-N’-ethylcarbodiimide) (186 mg, 0.97 mmol) followed by N- methylmorpholine (0.38 mL, 3.48 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 EtOAc as eluents to get the desired amide 10 (62.8 mg, 24 % yield) as a white solid compound. -NMR (400 MHz, DMSO-de): <514.66 (br s, 1H), 9.23 (br s, 1H), 8.49 (br s, 1H), 7.60-7.58 (m, 2H), 7.22 (d, J= 8.4 Hz, 1H), 4.43 (d, J= 6 Hz, 2H), 3.86 (s, 3H); 19F -NMR (376 MHz, DMSO-de): <5 -60.82 ppm. MH+ = 301.4 m/z. The synthetic route of 4928-87-4 has been constantly updated, and we look forward to future research findings. 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

Synthetic Route of 626248-56-4, 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. 626248-56-4, name is 3-(2H-1,2,3-Triazol-2-yl)aniline belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

A mixture of tert-butyl (1S,2R)-2-(5-bromo-6-cyanopyridin-3-ylamino)cyclohexylcarbamate (90 mg, 0.227 mmol), 3-(2H-1,2,3-triazol-2-yl)aniline (40 mg, 0.250 mmol), NaOPh trihydrate (50 mg, 0.294 mmol), xantphos (30 rng, 0.051 mmol) and Pd2dba3 (18 mg, 0.019 mmol) in dioxane (3 mL) was degassed with Ar, then was stirred at 110 C for 20 h. Water and EtOAc were added. Organic phase was separated, washed with aq. 1N NaOH, dried over Na2SO4, concentrated in vacuo to give tert-butyl (1S,2R)-2-(5-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-6-cyanopyridin-3-ylarnino)cyclohexylcarbamate, which was then dissolved in trifluoroacetic acid (5 mL). The solution was allowed to stand for 2 h. Excess of trifluoroacetic acid was removed in vacuo. The residue was purified by HPLC to give 3-(3-(2H-1,2,3-triazolyl)phenylamino)-5-((1R,2S)-2-aminocyclohexy]amino)picolinonitrile (70 mg).

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

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; SONG, Yonghong; XU, Qing; SRAN, Arvinder; BAUER, Shawn M.; JIA, Zhaozhong J.; KANE, Brian; PANDEY, Anjali; WO2013/192046; (2013); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 288-88-0, name is 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 288-88-0, name: 1H-1,2,4-Triazole

Example 91 Preparation of 4-(1H-1,2,4-triazol-1-yl)benzaldehyde (DI5) To a stirring solution of 4-fluorobenzaldehyde (10.0 g, 80.6 mmol) in DMF (150 mL) were added K2CO3 (13.3 g, 96.7 mmol) and 1,2,4-triazole (6.67 g, 96.7 mmol) and the resultant reaction mixture was stirred at 120 C. for 6 h. After completion of reaction (by TLC), the reaction mixture was diluted with water and extracted with EtOAc (3¡Á100 mL). The combined EtOAc layer was washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a solid (9.0 g, 65%): mp 145-149 C.: 1H NMR (400 MHz, CDCl3) delta 10.08 (s, 1H), 8.70 (s, 1H), 8.16 (s, 1H), 8.06 (d, J=8.0 Hz, 2H), 7.92 (d, J=8.0 Hz, 2H); ESIMS m/z 173.9 ([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, 1H-1,2,4-Triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US9211280; (2015); B2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 1455-77-2, These common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-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.

General procedure: Picric acid (0.22 g, 1.0 mmol) and 1H-1,2,4-triazole-3,5-diamine (0.09 g, 1.0 mmol) were mixed in a water-methanol mixture (v/vpercent, 1:4, 10 ml). The resulting solution was refluxed for 2 h and filt ered through celite. The filtrate was evaporated to dryness under vacuum and the yellow solid obtained was redissolved in methanol. salt 3 were obtained by slow evaporation 77.8percent (0.25 g) yield. Anal. Calcd. (percent) for C8H8N8O7 (328.22): C, 29.37; H, 2.15; N, 34.25. Found: C, 29.23; H, 2.05; N, 34.11. IR (KBr, cm-1): 3460, 3418, 3354, 3168, 1839, 1689, 1627, 1548, 1430, 1329, 1272, 1163, 1076, 999, 912, 788, 711, 656. 1H NMR (DMSO-d6, ppm) delta: 8.77 (s, 2H, picrate), 12.55 (s, br, 2H, NH), 6.43 (s, br, 4H, -NH2). 13C NMR (DMSO-d6, ppm) delta: 159.58, 156.02, 152.15, 140.92, 126.54, 125.21.

Statistics shows that 3,5-Diamino-1,2,4-triazole is playing an increasingly important role. we look forward to future research findings about 1455-77-2.

Reference:
Article; Goel, Nidhi; Singh, Udai P.; Singh, Gurdip; Srivastava, Pratibha; Journal of Molecular Structure; vol. 1036; (2013); p. 427 – 438;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, molecular formula is C8H8N4, 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. Product Details of 4922-98-9

Example 38; STEP A; To the solution of 3-phenyl-1H-1 ,2,4-triazol-5-amine (32 mg, 0.2 mmol) in DMA (0.5 ml_) was added ethyl 4-chloro-4,4-difluoro-3-oxobutanoate (40 mg, 0.2 mmol). The reaction mixture was stirred in microwave at 180 0C for 20 minutes, and then cooled to room temperature. The product, compound 38-1 , was purified by reverse phase HPLC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4922-98-9, its application will become more common.

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

Adding a certain compound to certain chemical reactions, such as: 1455-77-2, name is 3,5-Diamino-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 1455-77-2, HPLC of Formula: C2H5N5

3,5-Diamino-1,2,4-triazole was loaded into crystallization vessel inside a dry box. aHF (5?10 ml) was condensed onto the solid at 77 K and the reaction mixture was brought to ambient temperature. The resulting clear solution was decanted into the 6-mm o.d. side arm. Evaporation of the solvent from this solution was carried out by maintaining a temperature gradient of ca. 10?20 ¡ãC between both tubes for several weeks. Slow distillation of aHF from the 6-mm o.d. tube into the 19-mm o.d. tube resulted in growth of crystals compound II inside the 6-mm o.d. tube.

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; Goreshnik, Evgeny; Journal of Fluorine Chemistry; vol. 197; (2017); p. 94 – 99;,
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. 288-88-0, name is 1H-1,2,4-Triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Product Details of 288-88-0

General procedure: 1 mmol of the compound of the formula II-1 and 2 mmol of the compound of the formula III are sequentially added to the reaction.0.5mmol% catalyst CS Cu2O,3mmol potassium phosphate and 0.5ml N,N-dimethylformamide solution, heated to 110 C to stir the reaction,After the TLC reaction was completed, the reaction was quenched with water and filtered for ethyl acetate.Washed with saturated brine, dried and concentrated.The product was obtained by silica gel column chromatography.

The synthetic route of 288-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yancheng Jin Ming Pharmaceutical Co., Ltd.; Yancheng Normal College; Qian Cunwei; Feng Xuexin; Yang Zijian; Hu Chaojun; Qiu Yue; Wang Qingdong; Yang Jinming; (13 pag.)CN109608401; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 584-13-4, A common heterocyclic compound, 584-13-4, name is 4H-1,2,4-Triazol-4-amine, molecular formula is C2H4N4, 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.

General procedure: Compound 10 was prepared following apreviously published protocol. 4-Amino-4H-1,2,4-triazole (0.15 g, 1.72mmol) was added to a stirred mixture of 2,2′,4′-trichloroacetophenone (0.50 g, 2.24 mmol) in i-PrOH (3 mL). After stirring for 12 h at 80 C, the reaction mixture was cooled to rt and wasevaporated to dryness under reduced pressure to give a residue, which was dissolved in CH2Cl2(2 mL) and stirred for 30 min at 0 C. The precipitated solid was filtered and washed withCH2Cl2 (1 mL) to yield compound 10 (0.50 g, 94%) as a white solid.

The synthetic route of 584-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shrestha, Sanjib K.; Garzan, Atefeh; Garneau-Tsodikova, Sylvie; European Journal of Medicinal Chemistry; vol. 133; (2017); p. 309 – 318;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1338226-21-3, 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. 1338226-21-3, name is 3-(Chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-chloro-5-methyl-2-phenylphenol (62.2 mg, Intermediate Bi) inacetone (2 mL) was added K2C03 (42.6 mg) and 3-(chloromethyl)-4-methyl-1H-1,2,4-triazol- 5(4H)-one (35 mg, CAS: 1338226-21-3). The reaction mixture was stirred for 2 hours at reflux. The reaction mixture was poured on 10% aqueous NH4C1 solution (30 mL) and EtOAc (30 mL)and the layers were separated. The aqueous layer was extracted a second time with EtOAc (30 mL). The organic layers were washed with brine (30 mL), dried over MgSO4, filtered andconcentrated in vacuo. The residue was purified by silica gel chromatography on a 20 g column using an Flashmaster MPLC-system eluting with a gradient of DCM: MeOH (100/0 to 50/50) to give the title compound as an off-white solid (7 mg, 9%). MS (ESI): mlz = 330.100 [M+H].

The chemical industry reduces the impact on the environment during synthesis 3-(Chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; LUEBBERS, Thomas; MARTIN, Rainer E.; MATTEI, Patrizio; NEIDHART, Werner; RICHTER, Hans; RUDOLPH, Markus; PINARD, Emmanuel; (450 pag.)WO2017/37146; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics