Tag: M.W=0-100

Adding some certain compound to certain chemical reactions, such as: 288-36-8, name is 1H-1,2,3-Triazole, 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 288-36-8. 288-36-8

To a stirred solution of EE-1 (10 g, 144.79 mmol) in water (100 mL) is added EE-2 (13.73 g, 173.75 mmol) dropwise at 0 C and the reaction mixture is stirred at 0 C for 7 hours. The reaction mixture is filtered and extracted with diethyl ether. The combined organics are concentrated in vacuo to yield EE-3.

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 1H-1,2,3-Triazole.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HUGHES, Robert Owen; LI, Xiang; NEMOTO, Peter Allen; SMITH KEENAN, Lana Louise; WU, Lifen; XIONG, Zhaoming; (65 pag.)WO2018/111803; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 7170-01-6, name is 3-Methyl-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. 7170-01-6

For the preparation of [Zn(atz)2]¡¤guest (MAF-66), 73 mg of 3-amino-1,2,4-triazole (atz) was dissolved in 50 mL of isopropylalcohol and 40 mg of Zn(OH)2 was dissolved in 50 mL of a 25% aqueous ammonia solution. The solutions were mixed together and stirred for several minutes. The final solution was left at room temperature for 3 d to evaporate slowly. The obtained colorless crystals were centrifuged and washed three times with water and isopropyl alcohol, and then air-dried. Elem. Anal. Calcd. (%) for C7H15.2N8O1.6Zn ([Zn(atz)2]¡¤0.6H2O¡¤1.0C3H8O): C, 27.80; H, 5.07;N, 37.05; Zn, 21.62. Found: C, 27.83; H, 4.86; N, 37.02; Zn, 22.77.

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 7170-01-6.

Reference:
Article; Kim, Han-Ung; Babu, Robin; Roshan, Roshith; Park, Dae-Won; Applied Catalysis A: General; vol. 538; (2017); p. 59 – 65;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-88-0, name is 1H-1,2,4-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. 288-88-0

General procedure: A mixture of 4-fluoro acetophenone/4-fluorobenzaldehyde (10 mmol) and imidazole/triazole (10 mmol) were dissolved in dry DMF (20 mL). K2CO3 (12 mmol) was added in small portion within a period of 15 min to the above stirred solution. Mixture was stirred for 10-12 h at 110 C. Heating discontinued, K2CO3 was filtered off, filtrate extracted with ethyl acetate (3 ¡Á 15 mL). Organic layer was washed with water (3 ¡Á 15 mL), dried over anhydrous sodium sulphate and concentrated to given an oil which was purified on silica gel column (60-120 mesh) taking methanol: chloroform (1:99) as an eluent.

Statistics shows that 288-88-0 is playing an increasingly important role. we look forward to future research findings about 1H-1,2,4-Triazole.

Reference:
Article; Marrapu, Vijay K.; Chaturvedi, Vinita; Singh, Shubhra; Singh, Shyam; Sinha, Sudhir; Bhandari, Kalpana; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4302 – 4310;,
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. 288-36-8, name is 1H-1,2,3-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. 288-36-8

To a mixture of (2-iodophenyl)methanol [5159-41-1] (1.50 g, 6.41 mmol), 1 H-1 ,2,3-triazole (0.797 g, 11.54 mmol), trans-N, N’-dimethylcyclohexane-l ^-diamine [68737-65-5] (0.091 g, 0.641 mmol) and Cs2C03 (3.76 g, 1 1.54 mmol) in DMF (15 mL), Cul (0.61 g, 3.20 mmol) was added and the reaction mixture was stirred for 20 min at 120C and 15 min at 160C in the microwave. The reaction mixture was cooled to rt and filtered to remove the solids. The filtrate was concentrated under reduced pressure. The residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane) to yield the title compound (1.46 g, 64%). [1H NMR (400 MHz, DMSO-cfe) USD ppm 8.10 (s, 2 H), 7.74 (d, J=7.53 Hz, 1 H), 7.61 (dd, J=8.03, 1.25 Hz, 1 H), 7.52 (td, J=7.53, 1.25 Hz, 1 H), 7.44 (m, 1 H), 5.26 (t, J=5.40 Hz, 1 H), 4.59 (d, J=5.02 Hz, 2 H); LCMS RtA = 0.68, [M+H]+ = 176.1].

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BADIGER, Sangamesh; BEHNKE, Dirk; BETSCHART, Claudia; CHAUDHARI, Vinod; COTESTA, Simona; HINRICHS, Juergen Hans-Hermann; OFNER, Silvio; PANDIT, Chetan; WAGNER, Juergen; WO2011/76747; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-34-2, 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 7343-34-2 as follows.

In a 25 mL round-bottomed flask under N2 at 0 ¡ãC, sodium hydride (60percent in mineral oil, 0.059 g, 1.48 mmol) was added to a solution of 3,5-dimethyl-lH-l,2,4-triazole (0.112 g, 1.15 mmol) in DMF (5 mL) and the mixture was stirred for 30 min. To this mixture was then added 5-bromo-4′-(bromomethyl)-[l, r-biphenyl]-2-carbonitrile (1-002, 0.407 g, 1.16 mmol) and the mixture was stirred at RT for 3.5 h. The resulting mixture was then poured into H20 and the product was extracted with EtOAc (x3). The combined organic extract was washed with 0 (x3) and brine, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified on ISCO using a 40 g column (0-5percent MeOH-DCM) to afford the title compound (0.248 mg, 0.675 mmol, 59percent yield) as a colorless gum. LC (Method B): 1.795 min. MS (APCI): calcd for Ci8H16BrN4 [M + H]+ m/z 367.1, found 367.0. H NMR (400 MHz, CDC13) delta ppm 7.66 (dd, J = 0.78, 1.57 Hz, 1H), 7.61 – 7.63 (m, 2H), 7.51 – 7.56 (m, 2H), 7.28 – 7.31 (m, 2H), 5.29 (s, 2H), 2.42 (s, 3H), 2.38 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7343-34-2, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 288-36-8

A mixture of 2,3-difluorobenzonitrile (4.0 g, 28.8 mmol), 2H-1 ,2,3-triazole (1 .9 g, 28.8 mmol) in DMF (85.0 mL) and K2CO3 (7.9 g, 57.5 mmol) were heated to 125 C for 1 .5 h. After cooling to rt, water was added and the mixture extracted with EtOAc (2 X). The combined organics were washed with brine and dried (Na2SO4). Purification via FCC (10-100% EtOAc in hexanes) gave two products. 3-Fluoro-2-(2H-1 ,2,3-triazol-2- yl)benzonitrile (1 .6 g, 29%), 1H NMR (CDCI3): 7.99 (s, J = 6.6 Hz, 2H), 7.67 – 7.63 (m, 1 H), 7.61 – 7.53 (m, 2H), 7.26 (s, 6 H) and 3-fluoro-2-(1 H-1 ,2,3-triazol- 1 -yl)benzonitrile (2.0 g, 38%) 1H NMR (CDCI3): 7.97 (dd, J = 4.4, 2.8 Hz, 1 H), 7.95 (d, J = 1 .2 Hz, 1 H), 7.70 (tt, J = 5.7, 2.8 Hz, 1 H), 7.65 (td, J = 8.1 , 4.9 Hz, 1 H), 7.62 – 7.57 (m, 1 H).

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; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 288-36-8, name is 1H-1,2,3-Triazole, 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 288-36-8. 288-36-8

The molar ratio of 9,10-dibromoanthracene: 1H-1,2,4-triazole: potassium carbonate: copper oxide is 2: 10-15: 30: 1In the magnet,A 50 mL three-necked round bottom flask equipped with a reflux condenser and a thermometer was charged with CuO (0.0398 mg, 0.5 mmol)Potassium carbonate (2.0731 g, 15 mmol),Triazole (0.345 mg, 5 mmol),9,10-dibromoanthracene (0.3360 g, 1 mmol),20 mL DMF.Start stirring at 100 oC,Reaction for 24 hours.After the reaction,The reaction solution was cooled to room temperature,filter,The filtrate was added to 100 mL of water,Precipitation precipitation,Suction filtration, collecting filter cake,Yield 60%.

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 1H-1,2,3-Triazole.

Reference:
Patent; Tianjin Normal University; Wang Zhongliang; Guo Changcheng; Shang Yuntao; Zhang Zhigang; Yang Xi; Wang Ying; (10 pag.)CN106317119; (2017); A;; ; Patent; Tianjin Normal University; Wang Zhongliang; Yang Xi; Guo Changcheng; Shang Yuntao; Zhang Zhigang; Wang Ying; (11 pag.)CN106317121; (2017); A;; ; Patent; Tianjin Normal University; Wang Zhongliang; Yang Xi; Guo Changcheng; Shang Yuntao; Zhang Zhigang; Wang Ying; (11 pag.)CN106317120; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, Adding some certain compound to certain chemical reactions, such as: 288-36-8, name is 1H-1,2,3-Triazole, 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 288-36-8.

1,2,3-triazole(0.7 ), 2-iodo-benzoic acid (1.0 ), cesium carbonate (2.36 g, 7.20 mmol)Trans-N, N’-dimethyl-1,2-cyclohexanediamine (0.10 g, 0.75 mmol), cuprous iodide (0.08 g, 0.40 mmo 1), N, N-dimethyl Amide (18 mL)Were successively added to a 100 mL single-necked round bottom flask and gradually warmed to 100 C for 4 hours under nitrogen protection.The reaction was quenched, cooled, diluted with tap water and extracted with ethyl acetate (200 mL X).The aqueous layer was acidified with concentrated hydrochloric acid (rhoH- = 1 ~ 2) and extracted with ethyl acetate (200 mL x 2). The combined organic layers were dried and dried over anhydrous sodium sulfate. The filtrate was evaporated under reduced pressure and purified by column chromatography. (Dichloromethane / methanol (v / v) = 30/1) gave the title compound (yellow solid, 0.511 g, 67%)

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 288-36-8.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Wei Dehuo; Xue Yaping; Zhang Yingjun; (44 pag.)CN106674207; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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. 288-36-8

Step A: 6-methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrile To 3-bromo-5-methylpicolinonitrile (2.2 g, 11 mmol) in DMF (28 mL) was added K2CO3 (1.7 g, 12 mmol) and 2H-1,2,3-triazole (650 muL, 11 mmol). The mixture was heated to 100 C. for 36 h, cooled to rt and extracted with EtOAc. The combined organics were dried (Na2SO4) and concentrated. Purification via silica gel chromatography (10-100% EtOAc in hexanes) gave the title compound (1 g, 48%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-36-8, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; GELIN, Christine F.; LEBOLD, Terry P.; SHIREMAN, Brock T.; US2014/275118; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

Step A Synthesis of 8-methoxy-2-methyl-4-(5-methyl-l//-l,2,4-triazol-l-yl)quinoline and 8- methoxy-2-methyl-4-(3 -methyl- H- 1 ,2,4-triazol- 1 -yl)quinoline4-chloro-8-methoxy-2- methylquinoline (100 mg, 0.481 mmol) was reacted with 3-methyl- IH-l, 2,¡¤ 4-triazole (46.0, 0.554 mmol) according to the synthesis of 4-(4-fluoro- 1 /Y-pyrazol- 1 -yl)-8-mcthoxy-2-mcthylquinolinc to give a mixture of the title compounds. MS (m/z): 255.3 [M+H+] Step B Synthesis of 2-methyl-4-(3-methyl-l//-l,2,4-triazol-l-yl)quinolin-8-ol and 2-methyl- 4-(5-methyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolin-8-ol (0284) A mixture of 8-mcthoxy-2-mcthyl-4-(5-mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolinc and 8- mcthoxy-2-mcthyl-4-(3-mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolinc (153 mg, 0.602 mmol) was demethylated according to the synthesis of 4-(4-fluoro-l//-pyrazol-l-yl)-2-methylquinolin-8-ol to give a mixture of the title compounds. MS (m/z): 241.1 [M+H+] Step C. Synthesis of (5)-2-(l-(3-chloro-5-fluoro-2-((2-methyl-4-(5-methyl-l//-l,2,4-triazol-l- yl)quinolin-8-yloxy)methyl)phenyl)ethyl)isoindoline- 1 ,3-dione and (5)-2-(l -(3-chloro-5-fluoro-2- ((2-methyl-4-(3 -methyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolin-8-yloxy)methyl)phenyl)ethyl)isoindoline- l,3-dione (0286) A mixture of 2-mcthyl-4-(3-mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinol in-8-ol and 2-methyl-4-(5- mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinol in-8-ol (48.3 mg, 0.201 mmol) was reacted with (5)-2-(l-(3- chloro-2-(chloromethyl)-5-fluorophenyl)ethyl)isoindoline-l,3-dione (70.7 mg, 0.201 mmol) according to the synthesis of (5)-2-(l-(3-chloro-5-fluoro-2-((4-(4-fluoro-l/7-pyrazol-l-yl)-2- methylquinolin-8-yloxy)methyl)phenyl)ethyl)isoindoline-l,3-dione to give a mixture of the title compounds. MS (m/z): 556.4 [M+H+] Step D. Synthesis of (5′)- 1 -(3-chloro-5-fluoro-2-((2-mcthyl-4-(5-mcthyl- 1 H- 1 ,2,4-triazol- 1 – yl)quinolin-8-yloxy)methyl)phenyl)ethanamine and (5)- 1 -(3-chloro-5-fluoro-2-((2-methyl-4-(3- methyl- H- 1 ,2,4-triazol- 1 -yl)quinolin-8-yloxy)methyl)phenyl)ethanamine (0287) A mixture of (S)-2-( 1 -(3-chloro-5-fluoro-2-((2-mcthyl-4-(5-mcthyl- 1 H- 1 ,2,4-triazol- 1 – yl)quinolin-8-yloxy)methyl)phenyl)ethyl)isoindoline- 1 ,3-dione and (5)-2-(l -(3-chloro-5-fluoro-2- ((2-methyl-4-(3 -methyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolin-8-yloxy)methyl)phenyl)ethyl)isoindoline- l,3-dione (111 mg, 201 miho) was deprotected according to the synthesis of (5)-l-(3-chloro-5- fluoro-2-((4-(4-fluoro- l/ -pyrazol- 1 -yl)-2-methylquinolin-8-yloxy)methyl)phenyl)ethanamine to give the title compounds. MS (m/z): 448.3 [M+Na+] Step E. Synthesis of (5)-7V-(l-(3-chloro-5-fluoro-2-((2-methyl-4-(5-methyl-l//-l,2,4-triazol- l-yl)quinolin-8-yloxy)methyl)phenyl)ethyl)-2-(difluoromethoxy)acetamide and (S)-N-( 1 -(3- chloro-5-fluoro-2-((2-methyl-4-(3 -methyl- H- 1 ,2,4-triazol- 1 -yl)quinolin-8- yloxy)methyl)phenyl)ethyl)-2-(difluoromethoxy)acetamide (0289) A mixture of (/S’)- 1 -(3-chloro-5-fluoro-2-((2-mcthyl-4-(5-mcthyl- 1 H- 1 ,2,4-triazol- 1 – yl)quinolin-8-yloxy)methyl)phenyl)ethanamine and (5)- 1 -(3-chloro-5-fluoro-2-((2-methyl-4-(3- mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolin-8-yloxy)mcthyl)phcnyl)cthanaminc (19 mg, 43 mhio) was reacted with 2-(difluoromethoxy)acetic acid (7.2 mg, 56 mhio) according to the synthesis of (R)- N-((S)- 1 -(3-chloro-5-fluoro-2-((4-(4-fluoro- 1 /7-pyrazol- 1 -yl)-2-methylquinolin-8- yloxy)methyl)phenyl)ethyl)-2-hydroxypropanamide and purified by HPLC to yield (5′)-/V-( l -(3- chloro-5-fluoro-2-((2-methyl-4-(5-methyl- IH- 1 ,2,4-triazol- 1 -yl)quinolin-8- yloxy)methyl)phenyl)ethyl)-2-(difluoromethoxy)acetamide (MS (m/z): 534.2 [M+H+]) and ( S)-N – (1 -(3 -chloro-5-fluoro-2-((2-methyl-4-(3 -methyl- H- 1 ,2,4-triazol- 1 -yl)quinolin-8- yloxy)methyl)phenyl)ethyl)-2-(difluoromethoxy)acetamide (MS (m/z): 534.0 [M+H+])

The synthetic route of 3-Methyl-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARVARIS B.V.; GIBSON, Christoph; SAUPE, Joern; AMBROSI, Horst-Dieter; HAUSTEDT, Lars Ole; (99 pag.)WO2019/101906; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics