Tag: M.W=0-100

Electric Literature 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.

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+]

The synthetic route of 7170-01-6 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

Some common heterocyclic compound, 584-13-4, name is 4H-1,2,4-Triazol-4-amine, molecular formula is C2H4N4, 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. Application In Synthesis of 4H-1,2,4-Triazol-4-amine

General procedure: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), iodoalkene (1-4) or iodoarene (5-19) (1mmol) were dissolved in DMF (10mL) under argon in a three-necked flask equipped with a reflux condenser and a balloon on the top. Aminotriazole nucleophile (a, b or c) (1.2mmol) and triethylamine (0.5mL) were added. The atmosphere was changed to carbon monoxide. (Caution: High pressure carbon monoxide should only be used with adequate ventilation (hood) using CO sensors as well.) The reaction was conducted for the given reaction time upon stirring at 70C. The mixture was then concentrated and evaporated to dryness. Toluene (15mL) was added to the residue, the precipitate (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 584-13-4, its application will become more common.

Reference:
Article; Gergely, Mate; Boros, Borbala; Kollar, Laszlo; Tetrahedron; vol. 73; 48; (2017); p. 6736 – 6741;,
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 4923-01-7 as follows. Safety of 5-Methyl-4H-1,2,4-triazol-3-amine

General procedure: 3-Amino-1,2,4-triazole 8a-f (1.0 mmol), o-hydroxybenzaldehyde9a-e (1.0 mmol), acetone (10) (0.22 ml,3.0 mmol), and abs. EtOH (2 ml) were mixed in amicrowave process vial, and then 4 N solution of HCl indioxane (0.07 ml, 0.3 mmol) was added. The mixture wasirradiated at 150C for 30 min. The reaction mixture wascooled by an air flow and stirred for 24 h at roomtemperature for complete precipitation of the product. Theprecipitate was filtered off, washed with EtOH (1 ml) andEt2O (3¡Á1 ml), and dried. Compounds 1a-w were obtainedin a form of white solids.

According to the analysis of related databases, 4923-01-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guemue?, Mustafa K.; Gorobets, Nikolay Yu.; Sedash, Yuriy V.; Chebanov, Valentin A.; Desenko, Sergey M.; Chemistry of Heterocyclic Compounds; vol. 53; 11; (2017); p. 1261 – 1267; Khim. Geterotsikl. Soedin.; vol. 53; 11; (2017); p. 1261 – 1267,7;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27808-16-8, name is 4-Methyl-1H-1,2,3-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 27808-16-8, Computed Properties of C3H5N3

E) tert-butyl 6-methyl-5-(4-methyl-1H-1,2,3-triazol-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate To a solution of tert-butyl 5-chloro-6-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate (607 mg) in N,N-dimethylformamide (39.8 mL) were added 4-methyl-1H-1,2,3-triazole (208 mg) and potassium carbonate (378 mg). The reaction mixture was stirred at room temperature for 2 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (167 mg). MS (API+): [M+H]+315.1.

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kawasaki, Masanori; Mikami, Satoshi; Nakamura, Shinji; Negoro, Nobuyuki; Ikeda, Shuhei; Nomura, Izumi; Ashizawa, Tomoko; Imaeda, Toshihiro; Seto, Masaki; Sasaki, Shigekazu; Marui, Shogo; Taniguchi, Takahiko; (130 pag.)US2016/159808; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 584-13-4, name is 4H-1,2,4-Triazol-4-amine, 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 584-13-4, Safety of 4H-1,2,4-Triazol-4-amine

1.071 g of analytically pure dipyridinecarboxaldehyde and 0.841 g of analytically pure 4-amino-1,2,4-triazole, dissolved in 30 mL of analytical ethanol solution and heated to reflux for two hours to give the Schiff base ligand pyta. Yield 1.71 g, yield 98%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Guilin University of Technology; Zhang, Shuhua; Zhang, Shaonan; (7 pag.)CN106496188; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 1455-77-2, A common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, 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 MMB 14-O-succinate (2, 50 mg, 0.14 mmol) in dichloromethane was added EDC (40.26 mg, 0.21 mmol), HOBt (28.35 mg, 0.21 mmol), triethylamine (42.42 mg, 0.42 mmol) and the appropriate heterocyclic amine (0.14 mmol) at ambient temperature. The reaction mixture was stirred for 3-12 h at ambient temperature. When the reaction was complete (monitored by TLC), water was added and the resulting aqueous mixture was extracted with dichloromethane (2 * 10 mL). The organic layers were combined, washed with water followed by brine solution, and dried over anhydrous Na2SO4. The solvent was then evaporated under reduced pressure to afford the crude product. The crude product was purified by column chromatography (silica gel, 3-5% methanol in dichloromethane) to afford the desired succinamide analog as a white solid.

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

Reference:
Article; Janganati, Venumadhav; Ponder, Jessica; Thakkar, Shraddha; Jordan, Craig T.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry; vol. 25; 14; (2017); p. 3694 – 3705;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, 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. category: Triazoles

To a solution of 135.6 g (1.965 mol) of sodium nitrite in158.2 mL of water at -10 to -5 ¡ãC, we added a solution of 20 g(0.202 mol) of DAT in 423.7 mL 1.2 mol/L sulfuric acid for1.5 h. The reaction mixture was heated up to 60 ¡ãC and stirredfor another 1 h, then cooled the reaction mixture to roomtemperature. 67.2 mL 6 mol/L sulfuric acid and 11.85 g (0.121mol) aminosulfuric acid were added to reaction system andstirred for another 0.5 h, extracted with 322.5 ¡Á 3 mL of trioctylamineand 265.5 mL toluene, dried with magnesiumsulfate overnight. The magnesium sulfate was filtered and thefiltrate reacted with excess ammonia to obtain the yellow solid,dried in vacuum to give 25.1 g of 3,5-dinitro-1,2,4-triazoleammonium (AA DNT).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1455-77-2, its application will become more common.

Reference:
Article; Li, Ya-Nan; Liu, Ning; Su, Peng-Fei; Wang, Ying-Lei; Ge, Zhong-Xue; Li, Hui; Wang, Bo-Zhou; Asian Journal of Chemistry; vol. 26; 21; (2014); p. 7151 – 7156;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 288-88-0, 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 288-88-0 as follows.

(1) Sodium hydride (60% dispersion in mineral oil, 13.8 g, 345 mmol) was washed with hexane and suspended in DMF (150 ml). At an ice bath temperature, 1,2,4-triazole (total; 20.7 g, 300 mmol) was added thereto in four divisions. After stirring for 30 minutes, to the mixture was added tritylchloride (total; 83.7 g, 300 mmol) in seven divisions and additionally added DMF (50 ml). After stirring for 1.5 hours at room temperature, to the reaction mixture was added water (600 ml). The precipitated crystal was collected by filteration, washed with water, dissolved in CHCl3 (800 ml) and dried. The solvent was evaporated. The obtained residue was chromatographed on silica gel (ethylacetate:CHCl3=1:2, v/v). The fraction of the objective was concentrated to give 1-trityl-1H-1,2,4-triazole (43.9 g). Yield: 47%.

According to the analysis of related databases, 288-88-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shionogi & Co., Ltd.; US6620841; (2003); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 1455-77-2, 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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

It has been reported that the salts of 1,2,4-triazole and 3-amino-1,2,4-triazole could be obtained via an acid-base neutralization [29, 30]. Likewise, the LiDAtz with two amino groups on the triazole ring was prepared by the neutralization from equimolar 3,5-diamino-1H-1,2,4-triazole (DAtzH) and LiOH. Briefly, equimolar DAtzH and LiOH were added into deionized water separately, mixed and kept reacting and stirring at room temperature for 24 h, and the synthetic process is listed in Scheme 1. The product, a yellow powder, was obtained with 96.8% yield after evaporation of water and then drying at 120 C under vacuum for 24 h. 13C Nuclear magnetic resonance (NMR, 400 MHz, D2O): 161.73 ppm. Fourier transform infrared (FT-IR, KBr, cm-1) spectra: 3374, 3417 (w, nuNH2), 3335 (m, nuH2O), 1608 (m, deltaNH2), 1558 (m, nuC-N), 1475 (s, nuC-N), 1382 (m, nuC-N-C), 1070 (m, nuC-N), 688, 773 (w, deltaN-C-N). Elemental analyses (EA; C2H4N5Li, 105.06): found: C 13.22, H 2.20, N 78.42%; calculated: C 13.20, H 2.22, N 76.96%. High-resolution mass spectra [HRMS-electrospray ionization (ESI)]: m/z: [M+H+] calcd. for C2H5LiN5: 106.0700, found: 106.0700.

The chemical industry reduces the impact on the environment during synthesis 3,5-Diamino-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Fei, Yuqing; Liu, Shimin; Lu, Liujin; He, Yude; Deng, Youquan; Research on Chemical Intermediates; vol. 44; 12; (2018); p. 7187 – 7204;,
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. Computed Properties of C4H7N3

Under the protection of N2, a tetrahydrofuran (5.0 mL) solution of 1,4-dimethyl-1,2,3-triazole (0.56 g, 5.77 mol) was added dropwise to a tetrahydrofuran (5.0 mL) solution of butyllithium (2.77mL, 6.27 mol, 2.4 mol/L n-hexane solution) at -78C, and the resulting mixture was kept at -70C and reacted for 1h. Then chlorotributyltin (1.71 mL, 6.34 mol) was added. The system became clear, and was gradually warmed to room temperature. Water and ethyl acetate were added to the reaction flask, stirred for 15 min, and filtered through Celite filler, and the Celite filler was rinsed with ethyl acetate. After the filtrate was layered, the aqueous phase was extracted with ethyl acetate once. The ethyl acetate phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated to obtain a black residue. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (5:1) to obtain a luminous yellow oily product (1.40g, 63%). 1H NMR (400 MHz, CDCl3) delta 4.03 (s, 3H), 2.35 (s, 3H), 1.45-1.54 (m, 6H), 1.28-1.40 (m, 6H), 1.16-1.21 (m, 6H), 0.91 (t, 9H).

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

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; LI, Jijun; WU, Wei; ZHU, Yan; WANG, Huting; ZHAO, Lijia; HE, Weinan; SUN, Yinghui; PENG, Yong; HAN, Yongxin; (108 pag.)EP3412669; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics