Tag: M.W:100-200

These common heterocyclic compound, 7343-33-1, name is 5-Bromo-1H-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. Formula: C2H2BrN3

3-bromo-1H-1,2,4-triazole (9.6 g, 64.9 mmol), pyridine (10.5 mL, 129.8 mmol), copper (II) acetate (17.7 g, 97.3 mmol) and (3-fluorophenyl) boronic acid (11.4 g, 81.1 mmol) were mixed in DCM (200 mL) and the reaction was stined at room temperature for 3 days. The solid was filtered off and the filtrate was washed with water several times. The organic layer was dried, concentrated and purified on silica gel to afford 6.3 g of desired product JW-2c in 38percent yield. ?H NMR (400 MHz, CDC13) oe 8.45 (s, 1H), 7.54 – 7.47 (m, 1H), 7.45 (t, J = 7.5 Hz, 2H), 7.20 – 7.04 (m, 1H) ppm. ESI-MS m/z calc. 240.96509, found 242.27 (M+1)+; Retention time:0.75 minutes.

The synthetic route of 5-Bromo-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; DAVIES, Robert, J.; CAO, Jingrong; COCKERILL, Meghan, Elise; COLLIER, Philip, Noel; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GAO, Huai; GOLDMAN, Brian, Anthony; GREY, Ronald, Lee; GRILLOT, Anne-laure; GU, Wenxin; HENDERSON, James, A.; IRARRAZAVAL, Raul Eduardo, Krauss; KOLPAK, Adrianne, Lynn; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MALTAIS, Francois; MESSERSMITH, David; PIERCE, Albert, Charles; PEROLA, Emanuele; RYU, Elizabeth Jin-Sun; SYKEN, Joshua; WANG, Jian; (706 pag.)WO2016/197009; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-70-2, A common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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: To a stirred solution of 680 mg (1 .78 mmol) (3aR,4S,7R,7aS)-8-{[2-(trifluoro-methyl)phenyl]sulfonyl}octahydro-1H-4,7-epiminoisoindole hydrochloride (1 :1 ) (Intermediate 1) in 10 mL DMF were added 301 mg 1 H-1 ,2,3-triazole-4-carboxylic acid (2.66 mmol, 1 .5 eq), 590 mu 4-methylmorpholine (5.3 mmol, 3 eq) and 1 .01 g HATU (2.66 mmol, 1 .5 eq). After stirring for 16 h at RT, the solution was subjected to preparative HPLC to yield 473 mg (60 %) 1 H-1,2,3-triazol-5-yl[(3aR,4S,7R,7aS)-8-{[2-(trifluoromethyl)phenyl]sulfonyl}octahydro-2H-4,7-epiminoisoindol-2-yl]methanone. LC-MS (Method A1 ): Rt = 0.98 min; MS (ESIpos): m/z = 442 [M+H]+ 1 H NMR (400 MHz, DMSO-d6): delta [ppm] = 1 .40 – 1 .65 (m, 4 H) 2.80 – 3.01 (m, 2 H) 3.1 1 (dd, 1 H) 3.44 (dd, 1 H) 3.93 – 4.10 (m, 1 H) 4.23 (br s, 2 H) 4.39 (br s, 1 H) 7.83 – 7.96 (m, 2 H) 7.98 – 8.07 (m, 1 H) 8.23 – 8.29 (m, 1 H) 8.34 (br s, 1 H) 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 0.851 (1 .86), 1 .154 (4.18), 1 .171 (8.33), 1 .189 (4.15), 1 .232 (5.06), 1 .352 (1 .25), 1 .476 (3.05), 1 .498 (3.54), 1.545 (3.32), 1 .568 (2.64), 1.907 (4.52), 1 .987 (16.00), 2.006 (1.15), 2.332 (1 .00), 2.518 (4.20), 2.523 (3.25), 2.673 (1 .07), 2.686 (1 .44), 2.727 (2.10), 2.869 (1.54), 2.888 (4.37), 2.900 (1.51), 2.919 (1.42), 2.936 (1.81), 2.950 (1.59), 3.079 (1.93), 3.098 (1.95), 3.112 (2.32), 3.133 (1.78), 3.418 (1.78), 3.437 (1.88), 3.450 (2.13), 3.469 (1.64), 3.987 (3.57), 3.999 (1.42), 4.017 (5.50), 4.021 (3.40), 4.034 (3.49), 4.052 (1.15), 4.229 (4.91), 7.884 (3.44), 7.886 (3.44), 7.894 (3.96), 7.901 (8.45), 7.905 (3.69), 7.913 (4.08), 7.918 (4.32), 7.932 (1.44), 7.936 (1.00), 8.004 (4.86), 8.010 (4.74), 8.022 (2.59), 8.027 (3.37), 8.256 (4.32), 8.261 (3.10), 8.274 (4.15), 8.279 (3.47), 8.342 (1.47).

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SIEBENEICHER, Holger; STEUBER, Holger; TER LAAK, Antonius; NUBBEMEYER, Reinhard; ROTTMANN, Antje; IRLBACHER, Horst; BADER, Benjamin; PETERS, Michaele; WAGENFELD, Andrea; (110 pag.)WO2018/114677; (2018); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

2- [6-Chloro-3- (ethanesulfonyl) pyridin-2-yl] -3-methyl-6 – [(trifluoromethyl) sulfanyl]-3H-imidazo [4,5-b] pyridine 200 mg, 60percent sodium hydride (oily) 54 mg, and a mixture of 1 ml DMF, was added 3-bromo-1H-1,2,4-triazole 198mg under ice-cooling. After the mixture was stirred under ice-cooling for 2.5 hours, a saturated aqueous solution layer was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and saturated brine, and dried with anhydrous sodium sulfate. The resulting organic layer was dried under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 83mg of the present invention of compounds beta39 that described below.

The synthetic route of 7343-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; NAKAJIMA, YUJI; OKAWARA, YUICHI; (263 pag.)JP2016/102104; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 3641-08-5, name is 2H-1,2,4-Triazole-3-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 3641-08-5

Ribavirin biosynthesis was assayed using 5 × 109 colony-forming units (CFU) in 1 mL sodium phosphate buffer (30 mM, pH7.0) containing equimolar concentrations of uridine (Urd) and TCA(2.5 mM). Reactions were performed at 60C and 200 rpm in aperiod of 16 h.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3641-08-5.

Reference:
Article; De Benedetti, Eliana C.; Rivero, Cintia W.; Trelles, Jorge A.; Journal of Molecular Catalysis B: Enzymatic; vol. 121; (2015); p. 90 – 95;,
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. Computed Properties of C3H3N3O2

lH-l,2,3-triazole-5-carboxylic acid (3.1 mg, 27 muiotaetaomicron) was combined with HATU (10.4 mg, 27 muiotaetaomicron) in DMF (0.5 mL), and stirred for 10 minutes. DIPEA (4.8 mu, 27 Mmol) was added and the resulting mixture was stirred for 1 minute. Compound 2 (12 mg 27 muiotaetaomicron) dissolved in DMF (1 mL) was combined with added DIPEA (14.4 mu, 82 muiotaetaomicron) followed by addition of the activated acid solution. The resulting mixture was stirred for 30 minutes then purified by reverse phase chromatography (0-100% EtOAc/hexanes to yield Compound 3 (10

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.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 13423-60-4, name is 1-Phenyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H7N3

EXAMPLE 109 1-phenyl-4-(prop-1-yl)triazolium bromide 0.300 g (0.002 mol) 1-phenyltriazole 1 and 0.188 ml (0.254 g, 0.002 mol) 1-bromopropane 2 were dissolved in a pressure tube in 5 ml THF. The reaction mixture was stirred for 1 h at 50 C.; however, because no precipitate formed, the temperature was raised first to 80 (2 h) and then to 110 C. After 21 h at 110 C. the reaction mixture was cooled down. A DC check still indicated considerable amounts of the educt 1, so that additional 0.376 ml (0.508 g, 0.004 mol) of the educt 2 was added and stirring was continued for 24 h at 110 C. Subsequently, the reaction mixture was cooled down to room temperature and the same volume petroleum ether was added. The precipitated solid is filtered off, washed with petroleum ether and dried in HV. M 268.16 Yield: 0.0374 g (7%) 1H-NMR DM-102.w (300 MHz/DMSO): (ppm)=0.98 (t, 3H, 9-H); 3.95 (q, 2H, 8-H); 4.31 (t, 2H, 7-H); 7.70 (m, 3H, 5/5’/6H); 7.96 (d, 2H, 4/4′-H); 9.51 (s, 1H, 1-H); 11.00 (s, 1H, 2-H) 13C-NMR DM-102 (74.475 MHz/DMSO):

According to the analysis of related databases, 13423-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TECHNISCHE UNIVERSITAET DRESDEN; US2011/105761; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

[0742] To a solution of Compound 1 (15.9 mg, 30 f.tmol) indioxane (0.3 mL) was added HCI (149 f.LL, 598 fllllOI). Theresulting solution was stirred at room temperature for 2 hours,and then concentrated in vacuo. In a separate flask, a solutionof 3H-[1,2,3]triazole-4-carboxylic acid (4.1 mg, 36 f.tmol)and HATU (14 mg, 36 f.tmol) in DMF (0.3 mL) was stirred atroom temperature for 30 minutes. After this time, a solution ofthe crude amine in DMF (0.3 mL) was added, followed byDIPEA (16 f.LL, 90 f.tmol). The resulting solution was stirredfor 1 hour at room temperature then concentrated in vacuowhen the reaction was deemed complete by LCMS to yieldCompound 2 (16 mg), which was used without further purification.

The chemical industry reduces the impact on the environment during synthesis 1H-[1,2,3]Triazole-4-carboxylic acid. I believe this compound will play a more active role in future production and life.

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

Some common heterocyclic compound, 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, molecular formula is C3H4N4O2, 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. SDS of cas: 3641-13-2

General procedure: A mixture of benzil (0.01 mol), aldehydes (0.01 mol), 3-amino-1,2,4-triazole-5-carboxylic acid (0.01 mol), ammonium acetate (0.01 mol) and ceric ammonium nitrate (15 mol%) as a catalyst were refluxed in ethanol (15 mL) for about 3-4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was cooled to room temperature. The solid formed was filtered and dried. The crude products were recrystallized by ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3641-13-2, its application will become more common.

Reference:
Article; Nikalje, Anna Pratima G.; Ghodke, Mangesh S.; Kalam Khan, Firoz A.; Sangshetti, Jaiprakash N.; Chinese Chemical Letters; vol. 26; 1; (2015); p. 108 – 112;,
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, Safety of 1H-[1,2,3]Triazole-4-carboxylic acid

Example 20 3-{(R)-3-(5?-Chloro-2?-fluorobiphenyl-4-yl)-2-[(3H-[1,2,3]triazole-4-carbonyl)amino]propyl}tetrahydrofuran-3-carboxylic Acid (isomers a and b) [0453] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]tetrahydrofuran-3-carboxylic acid (isomer a; 10 mg, 24 mumol, 1.0 eq.) and DIPEA (20 muL, 100 mumol, 4.0 eq.) were dissolved in DMF (100 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 88 mumol, 3.7 eq.), HATU (15 mg, 39 mumol, 1.6 eq.), and DIPEA (40 muL, 200 mumol, 8.0 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for ten minutes, then both solutions were combined and stirred at room temperature and when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture; the organics were then separated, concentrated and purified by preparative HPLC to yield the title compound (isomer a; 7.8 mg). LCMS (ESI): calc. C23H22ClFN4O4=472; obs. M+H=473.0. Retention time: 4.73 min. [0455] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]tetrahydrofuran-3-carboxylic acid (isomer b; 10 mg, 24 mumol, 1.0 eq.) and DIPEA (20 muL, 100 mumol, 4.0 eq.) were dissolved in DMF (100 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 88 mumol, 3.7 eq.), HATU (15 mg, 39 mumol, 1.6 eq.), and DIPEA (40 muL, 200 mumol, 8.0 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for ten minutes, then both solutions were combined and stirred at room temperature. When the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture; the organics were then separated, concentrated and purified by preparative HPLC to yield the title compound (isomer b; 2.9 mg). LCMS (ESI): calc. C23H22ClFN4O4=472; obs. M+H=472.9. Retention time: 4.77 min. [0456] LC/MS Method: flow rate: 1.5 mL/min; Buffer A: 0.1% TFA/H2O; Buffer B 0.1% TFA/MeCN; gradient elution from 5-100% B over 9.6 min, then 100% B for 1.0 minute, detection at 254 nm.

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.; US2015/209352; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, 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. Quality Control of 4-Phenyl-1,2,4-triazolidine-3,5-dione

General procedure: Dimedone (0.14 g, 1 mmol), benzaldehyde (0.1 g, 1 mmol), and 4-phenylurazole (0.177 g, 1 mmol) were mixed with PEG-SO3H (0.6 g, 0.1 mmol) and the obtained mixture was stirred magnetically at 80 C for 40 min. After the completion of the reaction warm water (20 mL) was added and the mixture stirred for about 5 min. The insoluble crude product was filtered and recrystallized from EtOH/H2O 4:1 and the pure product was obtained (0.352 g, 91%). In order to recover the catalyst, the filtrate was dried under reduced pressure and recovered catalyst was washed with diethyl ether and reused after drying under reduced pressure. The equivalent procedure was used for the synthesis of triazolo[1,2-a]indazole-tetraones.

The synthetic route of 15988-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hasaninejad, Alireza; Zare, Abdolkarim; Shekouhy, Mohsen; Tetrahedron; vol. 67; 2; (2011); p. 390 – 400;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics