Category: Triazoles

Synthetic Route of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

A solution of 1H-1,2,3-triazole-4-carboxylic acid (26 mg, 0.23 mmol) and HBTU (171 mg, 0.45 mmol) in a mixed solvent of dimethyl sulfoxide (2 mL) and tetrahydrofuran (4 mL) was stirred for 10 min at rt, then (+/-) -cis-6- ( (3-aminocyclohexyl) amino) -2- (5, 7-difluoro -1-tosyl-1H-indol-3-yl) -5-fluoro-4-phenylnicotinonitrile (92 mg, 0.15 mmol) and DIPEA (0.10 mL, 0.61 mmol) were added into the mixture. The resulting mixture was stirred at rt overnight. To the reaction mixture was added water (30 mL) , and the mixture was extracted with EtOAc (30 mL ¡Á 3) . The combined organic layers were washed with a saturated aqueous sodium chloride solution (60 mL) , dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to dry, and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 5/1 1/5) to give the title compound as a white solid (78 mg, 73 %) . 1H NMR (400 MHz, CDCl3) delta (ppm) : 8.66 (s, 1H) , 8.20 (s, 1H) , 7.93 (d, J 8.0 Hz, 2H) , 7.71 (d, J 8.9 Hz, 1H) , 7.55 (s, 5H) , 7.31 (d, J 8.3 Hz, 2H) , 7.00 (s, 1H) , 6.84 (t, J 9.3 Hz, 1H) , 5.22 (d, J 5.7 Hz, 1H) , 4.30 (s, 1H) , 4.14 (d, J 7.2 Hz, 1H) , 2.58 (d, J 11.1 Hz, 1H) , 2.39 (s, 3H) , 2.29 (d, J 11.3 Hz, 1H) , 2.17 (d, J 11.0 Hz, 1H) , 1.97 (d, J 14.3 Hz, 1H) , 1.63 (m, 4H) .

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-[1,2,3]Triazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; ZHANG, Yingjun; (161 pag.)WO2018/41091; (2018); 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. 6818-99-1, name is 3-Chloro-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Chloro-1,2,4-triazole

STR18 A mixture of 34 g (246 mmol) of potassium carbonate and 35 g (338 mmol) of 3-chloro-1,2,4-triazole in 130 ml of acetone is refluxed. To this mixture there is added dropwise a solution of 50 g (169 mmol) of 2-bromo-4-chloro-1-(4-chlorophenyl)-butan-1-one in 60 ml of acetone. The mixture is boiled under reflux for a further 8 hours, the solid residue is then filtered off with suction, and the solvent is stripped off under reduced pressure. The residue which remains is taken up in ethyl acetate. The solution is washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue which remains is chromatographed on silica gel using dichloromethane as the eluent. Concentration of the elude by evaporation gives 42.9 g (90% of theory) of 1-(4-chlorobenzoyl)-1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropane in the form of a solid of melting point 85 C.

According to the analysis of related databases, 6818-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Aktiengesellschaft; US5096913; (1992); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 27996-86-7, 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 27996-86-7 as follows.

General procedure: To a glass vessel suitable for sealing with Teflon cap (for microwave vials) were added 1-(chloromethyl)-4,5-dimethoxy-2-nitrobenzene (1 equiv.) [34] and benzaldehyde derivative (3 equiv.) The vessel was capped and then evacuated and backfilled with N2 (thrice-repeated process). Anhydrous DMF (3.5mL/mmol) was introduced and the solution was vigorously stirred for 20minat-20C. TDAE (1.06 equiv.) was added slowly and the mixture was stirred for one hour. Then, the reaction was stirred at room temperature overnight. After LC-MS analysis clearly showed that the chloride had been totally consumed, the reaction was hydrolyzed with water. The mixture was then extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered off, and concentrated under reduced pressure to afford the corresponding crude product.

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:
Article; Da Costa, Laurene; Scheers, Els; Coluccia, Antonio; Rosetti, Alessia; Roche, Manon; Neyts, Johan; Terme, Thierry; Cirilli, Roberto; Mirabelli, Carmen; Silvestri, Romano; Vanelle, Patrice; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 528 – 541;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-65-5, These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-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.

Intermediate 53: step a (1-methyl-1H-1,2,3-triazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanol A 50 mL flask containing 1 -methyl- lH-l ,2,3-triazoie (0.47 g, 5.71 mmol) in dry THF (3 mL) was cooled to -43 C (CH3CN-CO2 bath). -Butyllithium (2.5 M in THF, 2.43 mL, 6.08 mmol) was then added dropwise resulting in a light blue suspension. The suspension was stirred at -40 C for 40 minutes, and then a homogeneous solution of 6-(trifluoromethyl)nicotinaldehyde (1 g, 5.71 nimol) in THF (7 niL) was introduced at -40 C, The resulting homogeneous colorless solution was allowed to warm gradually to room temperature, and after 30 minutes, LC/MS showed that the reaction was complete. The mixture was quenched with water and aqueous NH4CI and extracted with EtOAc (2 x). The combined organic extracts were washed with brine, dried over Na2S04, filtered and concentrated to provide the title compound as a semi-solid which was carried on to the next step without, further purification.

The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings.

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

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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, A new synthetic method of this compound is introduced below., Quality Control of 3,5-Diamino-1,2,4-triazole

Intermediate Example 36.0: 4-(2-Bromo-6-phenyl[1,2,4]triazolo[1,5- a]pyrimidin-5-yl)benzaldehyde; Stepi : 2-Amino-6-phenyl[1 ,2,4]triazolo[1 ,5-a]pyrimidine-5,7-diol; A solution of 9.Og 3,5-diamino-1 ,2,4-triazole and 22.4mL diethyl phenylmalonate in N,N-dibutylbutan-1-amine was heated under microwave irradiation to 1800C for 8h. The reaction mixture formed two layers after cooling to room temperature. The top layer was removed and the solvent of the lower layer was evaporated. The residue was treated with water and acidified with 5N HCI. The precipitated product was collected by filtration and dried. The crude product was used without further purification. MS (M+1): 244

The synthetic route of 1455-77-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; VENNEMANN, Matthias; MAIER, Thomas; HOeLDER, Swen; BENEKE, Gerrit; DEHMEL, Florian; ZUeLCH, Armin; STRUB, Andreas; BECKERS, Thomas; INCE, Stuart; REHWINKEL, Hartmut; LIU, Ningshu; BOeMER, Ulf; WO2010/91808; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 41253-21-8, 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 41253-21-8 as follows.

2-(1H-1,2,4-Triazol-1-yl)benzonitrile. A suspension of 2-fluorobenzylnitrile (3.0 g, 25 mmol) and 1,2,4-triazole sodium salt (2.4 g, 27 mmol) were stirred in tetrahydrofuran (7 mL) and dimethylformamide (14 mL) at 95 C. for 18 h. After cooling and concentrating, the product was crystallized from hot CH2Cl2/hexane (1:1) to give the title compound as a white solid (4.25 g, 100% yield). 1H-NMR (300 MHz, CDCl3) delta ppm: 8.74 (1H, s), 8.16 (1H, s), 7.82 (1H, dd, J=4.9, 1.3 Hz), 7.77-7.25 (2H, m), 7.57-7.51 (1H, m). LCMS [M+H]+ calcd for C9H7N4: 171.06. found: 171.12

According to the analysis of related databases, 41253-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 288-36-8, 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. 288-36-8 name is 1H-1,2,3-Triazole, 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.

Example 14: 5-[l-tert-Butyl-2-(2-l,2,3-triazol-2-yl-phenyl)-lH-benzimidazol-5-yl]- pyrimidin-2-ylamine and Example 15: 5-[l-tert-Butyl-2-(2-l,2,3-triazol-l-yl-phenyl)-lH-benzimidazol-5-yl]- pyrimidin-2-ylamine29% 13%To a solution of 5-[2-(2-bromo-phenyl)- l-ieri-butyl- lH-benzimidazol-5-yl]-pyrimidin-2- ylamine (refer to example 8, step 1) (57 mg, 0.14 mmol) in DMF (5 mL) are added 1Eta- 1,2,3-triazole (0.012 mL, 0.2 mmol), CuO (1 mg, 0.013 mmol), Fe(acac)3 (14 mg, 0.04 mmol) and Cs2C03 (88 mg, 0.27 mmol) at room temperature. The mixture is heated at 120 C for 96 hours and then cooled down and filtered. The filtrate is extracted with H20 (10 mL) and EtOAc (3 x 10 mL). The combined organic layer is dried with MgS04 and is filtered. The filtrate is concentrated and the residue is purified by silica gel chromatography eluting with 5% MeOH in CH2C12 to afford a less polar product 5-[l- ieri-butyl-2-(2- l,2,3-triazol-2-yl-phenyl)-lH-benzimidazol-5-yl]-pyrimidin-2-ylamine (Example 14) (16 mg, 29%) LCMS (ESMS): m/z 411.68 (M++l) as the major product and a more polar product 5-[l-ieri-butyl-2-(2-l,2,3-triazol-l-yl-phenyl)- lH- benzimidazol-5-yl]-pyrimidin-2-ylamine (Example 15) (7 mg, 13%) LCMS (ESMS): m/z 411.68 (M++l) as the minor product.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; CHEN, Zhidong; HAO, Ming-Hong; LIU, Weimin; LO, Ho-Yin; LOKE, Pui Leng; MAN, Chuk, Chui; MORWICK, Tina, Marie; NEMOTO, Peter, Allen; TAKAHASHI, Hidenori; TYE, Heather; WU, Lifen; WO2011/68821; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7170-01-6, name is 3-Methyl-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 7170-01-6, SDS of cas: 7170-01-6

DMF (1.5 ml) was added to a mixture of methyl 3-iodo-6-methyl-2-pyridinecarboxylate D44 (100 mg), 3-methyl-1H-1,2,4-triazole (45.0 mg, 0.541 mmol), (1R,2R)-N,N’-dimethyl-1,2-cyclohexanediamine (10.27 mg, 0.072 mmol), copper(I) trifluoromethanesulfonate benzene complex (9.08 mg, 0.018 mmol) and cesium carbonate (235 mg, 0.722 mmol) in a screw-topped vial. The mixture was degassed via 3 vacuum/nitrogen cycles and heated with shaking to 120 C. for 90 minutes. The reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in water/MeOH (1:1, 3 ml) and acidified to pH=2 by addition of 2 M HCl solution. The resulting mixture was evaporated to dryness under reduced pressure then the residue was triturated with DCM/MeOH (3:1, 5 ml). The mixture was filtered washing with more DCM/MeOH (3:1, 5 ml). The filtrate was treated with trimethylsilyldiazomethane solution (2 M in hexanes, 2 ml, 4 mmol) to re-esterify the acid. The reaction mixture was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (Biotage Snap 2¡Á10 g columns in series, EtOAc/Cy from 50/50 to 100/0) to give the title compound D84 (48 mg) as a colourless solid. UPLC (Acid FINAL_QC_POS): rt=0.45 minutes, peak observed: 233 (M+1). C11H12N4O2 requires 232. 1H NMR (400 MHz, CDCl3) delta ppm 2.52 (s, 3H) 2.73 (s, 3H) 3.91 (s, 3H) 7.47 (d, 1H) 7.81 (d, 1H) 8.32 (s, 1H).

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, 3-Methyl-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); 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. 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 103755-58-4

General procedure: To a solution of (1-aryl-1H-1,2,3-triazol-4-yl)methanol (2a-2c) [18] (10 mmol) in dry DMF (5 mL), anhydrous sodium hydride (15 mmol) was added and stirred for 5 min. After adding propargyl bromide (12 mmol), the resulting mixture was stirred at room temperature overnight. Upon completion of the reaction water (20 mL) was added and the whole was extracted with dichloromethane (3 ¡Á 30 mL). The combined organic layers were washed with brine and dried over Na2SO4. The organic layer was concentrated in vacuum and the residue was purified by silica gel (60-120 mesh) column chromatography using hexane-EtOAc, (7 : 3, v/v) as eluent to afford products 3a-3c as white solids. 1-Phenyl-4-[(prop-2-yn-1-yloxy)methyl]-1H-1,2,3-triazole (3a). Yield 89 %, white solid, mp 70-73 C. IR spectrum, nu, cm-1: 3221 (?C-H), 2108 (C?C), 1230 (N=N), 1064, 1041 (C-O). 1H NMR spectrum (400 MHz, CDCl3), delta, ppm: 7.99 s (1H, triazole H), 7.62 d (J = 8.9 Hz, 2H, Ar-H), 7.58 d (J = 8.9 Hz, 2H, Ar-H), 7.50 t (J = 7.3 Hz, 1H, Ar-H), 4.65 s (2H, OCH2), 4.20 s (2H, OCH2), 2.50 t (J = 2.4 Hz, 1H, ?C-H). 13C NMR spectrum (101 MHz, CDCl3) deltaC, ppm: 145.78, 140.09, 129.76, 128.63, 122.57, 121.70, 77.08, 74.22, 62.34, 57.33. Found, %: C: 67.57; H 5.17; N 19.68; O 7.47. C12H11N3O. Calculated, %: C 67.59; H 5.20; N 19.71; O 7.50. MS: M 214 [M + 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 103755-58-4.

Reference:
Article; Reddy; Reddy; Goud; Rao; Premkumar; Supriya; Russian Journal of General Chemistry; vol. 86; 6; (2016); p. 1424 – 1429; Zh. Obshch. Khim.; vol. 86; 6; (2016); p. 1424 – 1429,6;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 184177-83-1, 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. 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, 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.

2-(2(S)-Benzyloxy-l-ethyl-propyl)- 4- {4-[4-(4-hydroxy-phenyl)-piperazin- 1 -yl] -phenyl} -2,4-dihydro- [ 1 ,2,4]triazol-3-one (3 Og) was taken in 5N hydrochloric acid (60 ml) in methanol (300ml), and was hydrogenated for 2-3 hours under a hydrogen pressure of 4 kg/cm2 at 50 C in the presence of palladium on carbon (10%, 3g). After completion of reaction (monitored by TLC), the catalyst was filtered off and catalyst was washed with methanol (60 ml). The combined filtrate was concentrated and the resulting mass was dissolved in ethyl acetate (600ml) and refluxed for 1 hour. The resulting mixture was cooled, filtered to obtain 26g of the title compound having purity of 98.0% by HPLC.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 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, and friends who are interested can also refer to it.

Reference:
Patent; IND-SWIFT LABORATORIES LIMITED; WO2009/141837; (2009); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics