Day: March 16, 2021

Synthetic Route 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.

3H-l,2,3-triazole-4-carboxylic acid (3.4 mg, 30 muiotaetaomicron) was combined with HATU (1 1 mg, 30 muiotaetaomicron) in DMF (0.3 mL) and stirred at room temperature for 10 minutes; (1418) DIPEA (1 eq.) was added and the mixture was stirred for 1 minute. Compound 2 (10 mg, 30 muiotaetaomicron) in DMF (0.5 mL) was combined with DIPEA (5.2 muEpsilon, 30 muiotaetaomicron), then added to the activated acid solution. The resulting solution was stirred at room temperature for 30 minutes; LC/MS showed the mass of the desired product. The solvent was removed in vacuo and the crude residue was purified by reverse phase chromatography to yield Compound a (8.5 mg) as a TFA salt. MS m/z [M+H]+ calc’d for C27H31CIFN5O4, 544.21 ; found 545.2.

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

Some common heterocyclic compound, 184177-83-1, name is 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one, molecular formula is C30H35N5O3, 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. name: 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one

Add to a 50ml single-mouth bottle1-((2S,3S)-2-(Benzyloxy)-pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)- 1H-1,2,4-Triazole-5(4H)-one (1 g), 12 mol/L hydrochloric acid (5 ml) was stirred at 50 C.After 8 h, the dissolution was complete and TLC showed the reaction was complete.After cooling to room temperature, 6 mol/L NaOH (9 ml) was added, and NaHCO3 (10 ml) was evaporated, and water (10 ml) was added and stirred for 1 hour to form a solid. Filter by suction, wash the filter cake water (10ml),Recrystallization from isopropanol / toluene gave 0.7 g of a white solid, yield 85%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 184177-83-1, its application will become more common.

Reference:
Patent; Yangzijiang Pharmaceutical Group Co., Ltd.; Shanghai Pharmaceutical Industry Institute; Huang Huoming; Lv Huimin; Xiao Zhichao; Cai Wei; Ren Zhongjie; Zhou Ting; Liu Zhenren; Zhou Weicheng; Zhang Haibo; (35 pag.)CN108341754; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 7170-01-6, A common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-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.

To a solution of 3-methyl-1H-1,2,4-triazole (7.3 g, 88 mmol) in DMF (75 mL) was added K2CO3 (60.7 g, 439 mmol) and 2-bromopropionic acid tert-butyl ester (14.6 mL, 88 mmol). The reaction was stirred at room temperature overnight. The mixture was diluted with EtOAc (500 mL), washed with water (¡Á3) then brine. Dried over MgSO4 and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/isohexane (20 to 100%) to give 13 g of crude product as a 3:1 mixture of regioisomers. The mixture was purified by Chiralcel OD with a gradient from 4% to 30% IPA/Heptane. Then the first two peaks were separated with Chiracel OD column isocratically eluting with 4% IPA/Heptane. The second peak was collected as the desired single stereoisomer (R or S) (2-(3-methyl-1H-1,2,4-triaol-1-yl)propanoic acid tert-butyl ester) (3.5 g, 19%). 1H-NMR (500 MHz, CDCl3) delta 8.05 (s, 1 H), 4.90 (q, J=7 Hz, 1 H), 2.35 (s, 3 H), 1.72 (d, J=7 Hz, 3 H), 1.40 (s, 9 H). ESI-MS calculated for C10H17N3O2: Exact Mass: 211.13; Found 156.05 (-tBu).

The synthetic route of 7170-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berger, Richard; Chang, Lehua; Edmondson, Scott D.; Goble, Stephen D.; Ha, Sookhee Nicole; Kar, Nam Fung; Kopka, Ihor E.; Li, Bing; Morriello, Gregori J.; Moyes, Chris R.; Shen, Dong-Ming; Wang, Liping; Zhu, Cheng; US2009/253705; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1533519-84-4, 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 1533519-84-4 as follows.

The compound of Formula (4-B) (2.1 g, 6.53 mmol), the compound of Formula (5) (5.33 g, 19.92 mmol), sodium bicarbonate (2.19 g, 26.12 mmol) and N,N-dimethylformamide (10 mL) were combined in a flask and the resulting suspension was stirred at room temperature for 6 days. The reaction mixture (containing ?18 mol % of the compound of Formula (5) by 1H-NMR) was then poured onto ice water (60 mL) over 10 minutes whereupon a suspension formed. The formed suspension was stirred for 30 minutes during which time the solution was warmed to room temperature. The solid product was then collected by filtration, washed with water (4*8 mL), and suction dried for 15 minutes to provide a damp cake. A new flask was charged with the damp cake along with dichloromethane (75 mL), and the mixture stirred at room temperature for 30 minutes to afford a biphasic solution. The organic phase was removed and washed with water (3*30 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo at 30-35 C. to afford the compound of Formula (3-B) (5.78 g; 86% yield from the compound of Formula (4-B); HPLC purity=92 area %) as a light yellow foamy solid. 1H-NMR (CDCl3, 300 MHz) delta: 0.75-0.90 (6H, m), 1.15 (6H, d, J=8.50 Hz), 2.33-2.46 (3H, m), 3.96-4.20 (6H, m), 4.21-4.39 (4H, m), 5.27-5.36 (1H, m), 7.29-7.36 (6H, m), 7.36-7.43 (3H, m), 7.50-7.59 (3H, m), 7.59-7.68 (3H, m), 8.23 (1H, s), 8.25 (2H, s), 8.48-8.56 (3H, m).

According to the analysis of related databases, 1533519-84-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Apotex Inc.; Bodhuri, Prabhudas; Green, Melanie R. A.; Karadeolian, Avedis; Weeratunga, Gamini; Gorin, Boris; (33 pag.)US2018/258057; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 423165-07-5, A common heterocyclic compound, 423165-07-5, name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, molecular formula is C13H22N4, 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 an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C.

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:
Article; Viveka, T. Lakshmi; Sharada, L. Nalanda; Asian Journal of Chemistry; vol. 30; 9; (2018); p. 2029 – 2034;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 103755-58-4,Some common heterocyclic compound, 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, molecular formula is C9H9N3O, 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: 1-Azido-4-methylbenzenes 1 (0.3 mmol), propargyl alcohol 2 (0.36 mmol), CuI (0.03 mmol),NaAsc (0.06 mmol), and 2 mL solvent were added to a 15 mL pressure tube. The tube was thensealed, and the mixture was stirred at 80 C for 5 hours. After the reaction completed, the abovesystem was added with KMnO4 (0.75 mmol) and Na2CO3 (0.45 mmol), and stirred at 80 C for 8h until the reaction completed. Then, Ag2O (0.03 mmol) and K2S2O7 (0.6 mmol) were added tothe tube and the mixture was conducted at 100 C for 24 h until the transformation finished byTLC analysis. H2O (25 mL) was added to the mixture and the system was extracted with EtOAc (3¡Á 20 mL). The combined organic layer was washed with brine (3 ¡Á 5 mL), dried with Na2SO4, andconcentrated under reduced pressure to afford the crude product. Purification by columnchromatography on silica gel with EtOAc-PE (1:3) afforded the desired product 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, its application will become more common.

Reference:
Article; Han, Chunmei; Dong, Suping; Zhang, Wensheng; Chen, Zhen; Synlett; vol. 29; 5; (2018); p. 673 – 677;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 342617-08-7, 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 342617-08-7 as follows.

Step 2: [3-(3-Bromophenyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate A slurry of 3-(3-bromophenyl)-1H-1,2,4-triazole (58.5 g; 261 mmol; Step 1 above), anhydrous K2CO3 (43.2 g; 313 mmol), and chloromethylpivalate (45 mL; 313 mmol) in dry MeCN (250 mL) was heated to 80 C. (Note 1) for 1 hour. The mixture was cooled, solid was collected by filtration and the filtrate was concentrated in vacuo. Residue from the filtaret was combined with the filtered solid and the whole was stirred with water approximately 20 minutes. Solid was collected by filtration, washed with water (*3) and recrystallized from MeOH/water, affording the title compound as a colorless solid. LC/MS (method E) tR 0.88 min, m/z 338, 340 (M+H, Br isotopes).

According to the analysis of related databases, 342617-08-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smithkline Beecham Corporation; US2011/124559; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature 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.

Method 1: Diacetoxycopper (2.30 g, 12.7 mmol), 3,5-difluorophenyl-boronic acid (1.60 g, 10.1 mmol), 3-bromo-1H-1,2,4-triazole (1.25 g, 8.4 mmol) and 4A molecular sieve (150mg) were mixed in DCM (50 mL), and pyridine (1.3 mL, 16.90 mmol) was added. The mixture was stined at RT under air for 3 days. LCMS showed that no starting material remained and desired product was formed. The reaction was filtered through a plug of Celite via suction and the solid was washed with additional DCM (200m1). The combined organic layer was washed with 0.1 N aqueous HC1 three times (50 ml x 3) and brine (200 ml). The organic layer was concentrated and purified on silica gel (120 g column, dry loading method on Celite) using 10-90percent EtOAc:Hexanes to afford 1.23 g (50percent) of desired product JW-lc. ?H NMR (400 MHz, DMSO-d6) oe 9.40 (s, 1H), 7.78 – 7.61 (m, 2H), 7.41 (tt, J = 9.3, 2.3 Hz, 1H) ppm. ESI-MS m/z calc. 258.95566, found 260.05 (M+1)+; Retention time: 0.8 minutes.

The synthetic route of 7343-33-1 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

60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, 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. category: Triazoles

A mixture of 7-bromo-5-nitroisoquinolin-1(2H)-one (293b, 4.00 g, 14.9 mmol), 1,4-dimethyl-1H-1,2,3-triazole (2.17 g, 22.3 mmol), palladium acetate (334 mg, 1.49 mmol), CatacXiumA (butyl di-1-adamantylphosphine) (1.10 g, 2.97 mmol), and potassium acetate (7.30 g, 74.3 mmol) in 2-methyl-2-butanol (100 mL) was degassed with nitrogen, and heated at 120 C. in a sealed tube overnight. After cooling down room temperature, the reaction mixture was partitioned between ethyl acetate (300 mL) and water (300 mL). The organic phase was separated, washed with brine (1*300 mL), dried over sodium sulfate, concentrated to dryness, and purified by silica gel chromatography (eluting with a gradient of 0%-10% methanol in ethyl acetate), affording 7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one (293c, 2.55 g, 60% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) delta 11.95 (br. s., 1H), 8.57 (s, 2H), 7.55 (d, J=5.38 Hz, 1H), 6.98 (d, J=7.34 Hz, 1H), 4.00 (s, 3H), 2.29 (s, 3H). MS: 284 [M-1].

The synthetic route of 60166-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; EDWARDS, Martin Paul; KUMPF, Robert Arnold; KUNG, Pei-Pei; MCAPLINE, Indrawan James; NINKOVIC, Sacha; RUI, Eugene Yuanjin; SUTTON, Scott Channing; TATLOCK, John Howard; WYTHES, Martin James; Zehnder, Luke Raymond; US2014/179667; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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 956317-36-5

Compound (R)-I will be implemented in Preparation Example 1 -1 (5.54g, 20mmol, ee> 99%) is placed dichloro Methane (100 mL) and added triethylamine (12g, 120mmol), stirred for 1 hour at room temperature, mixing, Cooled to 0 C, the acid chloride solution prepared above was added dropwise to the mixture was slowly warmed to room temperature, After stirring for 16 hours. After completion of the reaction, adding 50mL of dichloromethane was added a saturated aqueous Aqueous sodium hydroxide (40 ml), the aqueous layer separated, the organic phase was washed with aqueous saturated sodium chloride, Dried over anhydrous magnesium sulfate to give a brown oil, ethyl acetate: n-heptane (volume ratio 5: 1) Decolorization and recrystallization to give a pale yellow waxy solid 7.4g, namely compound 10 in 95% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 956317-36-5, its application will become more common.

Reference:
Patent; CR Double-Crane Pharmaceuticals Co., Ltd; Liu, Kaixiang; Ma, Hongmin; Li, Kai; (22 pag.)CN105367506; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics