Tag: M.W:100-200

Application of 4928-87-4,Some common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, molecular formula is C3H3N3O2, 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.

Step 5: Preparation of 1-(5-((1 R,3s,5S)-8-(4H-1 ,2,4-triazole-3-carbonyl)-8- azabicyclo[3.2.1]octan-3-yl)-7-amino-3-(6-(1 -methyl-1 H-pyrazol-3-yl)pyridin- yl)pyrazolo[1 ,5-a]pyrimidin-6-yl)ethanone 1 H-1 ,2,4-triazole-3-carboxylic acid (58.0 mg, 0.51 mmol), EDC (133.7 mg, 0.70 mmol), HOBt (94.5 mg, 0.70 mmol) and DIEA (730 uL, 4.20 mmol) were added to a mixture of 1-(7-amino-5-((1 R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl)-3-(6-(1- methyl-1 H-pyrazol-3-yl)pyridin-3-yl)pyrazolo[1 ,5-a]pyrimidin-6-yl)ethanone (207.7 mg, 0.47 mmol) in DMF (5 mL) and the mixture was stirred at room temperature for 1 h. Purification with prep-LC provided 1-(5-((1 R,3s,5S)-8-(4H-1 ,2,4-triazole-3- carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)-7-amino-3-(6-(1 -methyl-1 H-pyrazol-3- yl)pyridin-3-yl)pyrazolo[1 ,5-a]pyrimidin-6-yl)ethanone.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2,4-Triazole-3-carboxylic acid, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SCHERING CORPORATION; SIDDIQUI, M. Arshad; NAN, Yang; PATEL, Mehul, F.; REDDY, Panduranga Adulla P.; MANSOOR, Umar Faruk; MENG, Zhaoyang; VITHARANA, Lalanthi Dilrukshi; ZHAO, Lianyun; MANDAL, Amit, K.; LIU, Duan; TANG, Shuyi; MCRINER, Andrew; BELANGER, David, B.; CURRAN, Patrick, J.; DAI, Chaoyang; ANGELES, Angie, R.; YANG, Liping; DANIELS, Matthew Hersh; WO2011/90935; (2011); 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 15988-11-1 as follows. Computed Properties of C8H7N3O2

General procedure: General procedure: A mixture of 4-phenylurazole (1, 1 mmol), aryl aldehyde (2, 1.1 mmol) or ketone (5, 1.1 mmol), 1,3-diketone (3, 1 mmol) and FeCl3 (16.2 mg, 10 mol%) in acetonitrile (2.5 mL) was stirred in preheated oil bath at reflux for a specified time as required to complete the reaction (see Table 2 and 3). After complete conversion, as indicated by TLC, the solvent was removed in vacuo and the residue was diluted with water and extracted with ethyl acetate (2¡Á10 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (Merck, 60-120 mesh, ethyl acetate:hexane, 4:6) to afford the pure triazolo[1,2-a]indazoletrione or spirotriazolo[1,2-a]indazoletetraonederivative.

According to the analysis of related databases, 15988-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Subba Reddy; Umadevi; Narasimhulu; Yadav; Chemistry Letters; vol. 42; 8; (2013); p. 927 – 929;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7343-33-1, A common heterocyclic compound, 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, molecular formula is C2H2BrN3, 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.

Copper(II) acetate (approximately 18.42 g, 101.4 mmol), 3-bromo-1H-1,2,4-triazole (10 g, 67.59 mmol), and 4 A molecular sieves (250 mg/0.33 mmol) were combined in dichloromethane and treated with 3,4-difluorophenyl boronic acid (14.94 g, 94.63 mmol), and pyridine (approximately 10.69 g, 10.93 mL, 135.2 mmol). The mixture was stirred at room temperature under air for 3 days. The reaction was filtered and the solid was washed with additional dichloromethane (200 mL). The combined organic layers were concentrated with silica gel and dry-loaded to purify on silica gel to afford 3-bromo-1-(3,4-difluorophenyl)-1,2,4-triazole (10.5 g, 54percent). MR (400 MHz, DMSO-^e) delta 9.30 (s, 1H), 8.08 – 7.96 (m, 1H), 7.77 – 7.62 (m, 2H) ppm. ESI-MS m/z calc. 258.95566, found 260.32 (M+l)+; Retention time: 0.96 minutes.

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; VERTEX PHARMACEUTICALS INCORPORATED; BETHIEL, Randy Scott; CAO, Jingrong; COLLIER, Philip, N.; DAVIES, Robert J.; DOYLE, Elisabeth; FRANTZ, James Daniel; GOLDMAN, Brian Anthony; GREY, Ronald Lee; GRILLOT, Anne-laure; GU, Wenxin; KOLPAK, Adrianne Lynne; KRAUSS, Paul Eduardo; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MESSERSMITH, David; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; WANG, Jian; (491 pag.)WO2018/106646; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 252742-72-6, 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. 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 108; 5-({[(4-bromophenyl)methyl]thio}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one; [Show Image] To a solution of 5-(chloromethyl) -2,4-dihydro-3H-1,2,4-triazol-3-one obtained according to the methods described in Tetrahedron Letter, 2000, 41, 8661 and the like (2.00 g, 15.0 mmol), (4-bromophenyl)methanethiol (3.04 g, 15.0 mmol) and potassium carbonate (2.48 g, 0.369 mmol) in THF (4 mL) was added a suspension of O-(trimethylsilyl)hydroxylamine (0.271 mL, 18.0 mmol) in DMF (40 mL) at room temperature, and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. The solid was washed with water and diethyl ether to give the title compound as a white powder (3.97 g, 88percent). 1H-NMR (300MHz, DMSO-d6) delta: 3.36 (2H, s), 3.70 (2H, s), 7.28 (2H, d, J = 8.3 Hz), 7.52 (2H, d, J = 8.3 Hz), 11.29 (1H, br), 11.39 (1H, br).

The chemical industry reduces the impact on the environment during synthesis 3-(Chloromethyl)-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; Takeda Pharmaceutical Company Limited; EP1953148; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 135242-93-2,Some common heterocyclic compound, 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, molecular formula is C4H7N3O, 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 1-Methyl-1,2,4-triazole-3-methylamine hydrochloride 1-Methyl-1,2,4-triazole-3-methanol (500 mg, 4.4 mmol) was added to ice-cold thionyl chloride (5 ml, 69 mmol). The mixture was heated at reflux for 0.75 h, then cooled to room temperature and evaporated in vacuo. The residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution and the aqueous layer separated and further extracted with dichloromethane (*2). The combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was treated with 33% w/w aqueous ammonia (5 ml) and the mixture heated in a sealed tube at 80 C. for 16 h. After cooling to room temperature, the reaction mixture was evaporated in vacuo and azeotroped with ethanol to give the title-amine (600 mg, 92%), 1H NMR (250 MHz, d6-DMSO) delta 3.88 (3H, s, Me), 4.04 (2H, s, CH2), 8.36 (2H, br s, NH2), 8.58 (1H, s, Ar-H).

The synthetic route of 135242-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Limited; US6200975; (2001); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, 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 1001401-62-2, Recommanded Product: 1001401-62-2

EXAMPLE 2 (2-(2H- 1 ,2,3-triazol-2-yl)phenyl)(4-(4,6-dimethylpyrimidin-2-yl)- 1 ,4-diazepan- 1 -yl)methanone To a solution of l-(4,6-dimethylpyrimidin-2-yl)-l,4-diazepane hydrochloride 1-2 (1.4 g, 5.2 mmol), 2-(2H-l,2,3-triazol-2-yl)benzoic acid Int E (1.1 g, 5.7 mmol), EDC (1.5 g, 7.8 mmol), and l-hydroxy-7-azabenzotriazole (1.1 g, 7.8 mmol) in DMF (10 mL) was added DIPEA (4.5 mL, 26 mmol) and the mixture was stirred at room temperature for 16 h. The solvent was concentrated in vacuo and the crude residue was redissolved in DCM and purified by silica gel chromatography (100% hexanes, 2 min; 0-100% EtOAc/hexanes, 20 min; 100% EtOAc, 4 min) to provide Example 2 (1.5 g) as a white solid. MS (ESI) m/z: 378.4 (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, 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; ROECKER, Anthony, J.; WO2015/95111; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 815588-93-3,Some common heterocyclic compound, 815588-93-3, name is 1-Methyl-1H-1,2,4-triazole-5-carboxylic acid, molecular formula is C4H5N3O2, 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 mixture of 1 -methyl-1 H-1 ,2,4-triazole-5-carboxylic acid (7.0 g, 55.1 mmol) in SOCI2 (20 mL) was heated to 70 ¡ãC for 2 h. The mixture was concentrated to dryness. The residue was dissolved in NH3/MeOH (7M, 40 mL) and stirred at rt overnight. The precipitated solid was filtered off, extracted with Et20 and dried under reduced pressure to give 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 1-Methyl-1H-1,2,4-triazole-5-carboxylic acid, its application will become more common.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; DEUSCHLE, Ulrich; ALBERS, Michael; HOFFMANN, Thomas; (95 pag.)WO2018/141857; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic 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. Quality Control of 1H-[1,2,3]Triazole-4-carboxylic acid

[0784] 1H-1,2,3-triazole-5-carboxylic acid (3.4 mg, 30f.tmol) was combined with HATU (11 mg, 30 f.tmol) in DMF(0.3 mL) stirred at room temperature for 10 minutes; DIPEA(1 eq.) was added and the mixture was stirred for 1 minute.Compound 2 (10 mg, 30 f.tmol) was dissolved in DMF (0.5mL) and DIPEA (5.2 f.LL, 30 f.tmol) was added, followed byaddition of the activated acid solution. The mixture wasstirred at room temperature for 30 minutes, after which timeLCMS indicated desired product formation. Half of the crudeproduct was purified using reverse phase chromatography toyield Compound a as a TFA salt (1 mg). MS m/z [M+Htcalc’d for C26H31CIFN50 4 , 532.21. found 532. Half of thecrude product was carried to the next step without furtherpurification.

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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 16681-70-2, Quality Control of 1H-[1,2,3]Triazole-4-carboxylic acid

[0769] 3H-1,2,3-triazole-5-carboxylic acid (2.5 mg, 22f.tmol) was combined with HATU (8.4 mg, 22 flillOI) in DMF(0.3 mL) and stirred for 10 minutes; Et3N (1 eq.) was addedand the mixture was stirred for 1 minute. Compound 2 (22f.tmol) was dissolved in DMF (0.5 mL) and Et3N (3.1 f.LL, 22f.tmol) was added, followed by addition of the activated acidsolution. The mixture was stirred for 30 minutes, concentrated,and purified by preparative HPLC to yield Compounda (8 mg) as a TFA salt. MS m/z [M+Ht calc’d forC26H29CIFN50 3 , 514.19. found 514.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-[1,2,3]Triazole-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1001401-62-2, name is 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. Recommanded Product: 2-(2H-1,2,3-Triazol-2-yl)benzoic acid

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(WSCHCl) (37.4 g, 0.20 mol) was added to a solution of Nethyl-2[3-(5-fluoro-pyridin-2-yl)-1H-pyrazol-1-yl] ethanaminedihydrochloride (50 g, 0.16 mol), 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (33.9 g, 0.18 mol), 1-hydroxy-1H-benzotriazolehydrate (HOBtH2O) (26.4 g, 0.20 mol) and triethylamine (TEA)(39.5 g, 0.39 mol) in THF (500 mL) at 0 C, followed by stirring atroom temperature for 20.5 h. The solvent of the reaction solutionwas distilled off under reduced pressure. An aqueous NaHCO3 solutionand EtOAc were added to the resulting residue, followed byextraction with EtOAc. The organic layer was washed with water,and the solvent was distilled off under reduced pressure to yieldthe crude product (72 g). An additional 196.7 g of the crude productwas synthesized using the same method from N-ethyl-2[3-(5-fluoro-pyridin-2-yl)-1H-pyrazol-1-yl] ethanamine dihydrochloride(140 g, 0.46 mol) and 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoicacid (94.8 g, 0.50 mol). The obtained crude product (268.7 g) wasrecrystallized with heptane and EtOAc. The deposited solid wasthen collected by filtration. The obtained solid was dried by heatingunder reduced pressure to yield the title compound 27e as acolorless powder (217.3 g).

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

Reference:
Article; Suzuki, Ryo; Nozawa, Dai; Futamura, Aya; Nishikawa-Shimono, Rie; Abe, Masahito; Hattori, Nobutaka; Ohta, Hiroshi; Araki, Yuko; Kambe, Daiji; Ohmichi, Mari; Tokura, Seiken; Aoki, Takeshi; Ohtake, Norikazu; Kawamoto, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 23; 6; (2015); p. 1260 – 1275;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics