Day: January 22, 2021

Electric Literature of 584-13-4, 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. 584-13-4 name is 4H-1,2,4-Triazol-4-amine, 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.

General procedure: To the solution of 4-amino-4H-1,2,4-triazole (0.0059 mol, 0.500 g) in an hydrous acetonitrile (20 mL), an N-alkyl or N-arylisothiocyanate (0.0065 mol) was introduced, and the obtained mixture was stirred at room temperature for 16h. Then the solvent was evaporated. The main compound was isolated from the reaction mixture by column chromatography (CHCl3: CH3OH; 9.5:1 vol.) or crystallized from acetonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4H-1,2,4-Triazol-4-amine, and friends who are interested can also refer to it.

Reference:
Article; Bielenica, Anna; Kedzierska, Ewa; Fidecka, Sylwia; Maluszynska, Hanna; Miroslaw, Barbara; Koziol, Anna E.; Stefanska, Joanna; Madeddu, Silvia; Giliberti, Gabriele; Sanna, Giuseppina; Struga, Marta; Letters in drug design and discovery; vol. 12; 4; (2015); p. 263 – 276;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 22300-52-3, 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. 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

To a 20-L round- bottom flask were placed 4,5-dibromo-2H-1,2,3-triazole (500 g, 2.20 mol), DCE (5 L), 2-methylfuran (5 L), cyclopropylboronic acid (379 g, 4.41 mol), Cu(OAc)2(401 g, 2.20 mol), 2,2-bipyridyl (344 g, 2.21 mol) and sodium carbonate (467 g,4.41 mol). The mixture was stirred overnight at 80 ¡ãC. After the reaction was cooled to room temperature, the mixture was filtered. The filtrate was concentrated under vacuum, dissolved in 5 L of EtOAc, washed with 2×1 L of 1 N hydrogen chloride and then with lxi L of brine, dried over sodium sulfate(Na2SO4), and concentrated under vacuum to afford the product.

The synthetic route of 4,5-Dibromo-2H-1,2,3-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong R.; CHO, Aesop; BUENROSTRO, Ana Zurisadai Gonzalez; HAN, Xiaochun; JABRI, Salman Y.; MCFADDEN, Ryan; QI, Yingmei; VOIGT, Johannes; YANG, Hong; XU, Jie; XU, Lianhong; (545 pag.)WO2019/75291; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 15294-81-2, name is 4,5-Dibromo-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 15294-81-2, Product Details of 15294-81-2

Intermediate 14e (0554) 4,5-Dibromo-2-methyl-2H-l,2,3-triazole Batch 1 : To a solution of 4,5-dibromo-lH-triazole (Intermediate 14f; 490.00 g, 2.16 mol) in DMF (3.2 L) was added potassium carbonate (358.23 g, 2.59 mol). The mixture was cooled to -10¡ãC under a nitrogen atmosphere and iodomethane (147.91 mL, 2.38 mol) was added dropwise. The reaction was then stirred at 25¡ãC for 16 hours. Batch 2: To a solution of 4,5-dibromo-lH-triazole (Intermediate 14f; 400 g, 1.76 mol, 1.00 eq) in DMF (2.8 L) was added potassium carbonate (291.9 g, 2.11 mol). The mixture was cooled to – 10¡ãC under a nitrogen atmosphere and iodomethane (131.48 mL, 2.11 mol) was added dropwise. The reaction was then stirred at 25¡ãC for 16 hours. Batches 1 and 2 were then combined and the reaction was quenched by the addition of water (4.2 L) and the aqueous phase extracted with MTBE (7 L x 3). The organic extract was concentrated under vacuum to approximately 700 mL and isopropanol (2 L) was added dropwise. This mixture was then stirred at 25 ¡ãC for 2 hours and the resulting precipitate filtered and dried under vacuum to afford undesired 4,5-dibromo-l-methyltriazole (220 g, 23.5percent) as a solid which showed the following NMR spectral data: FontWeight=”Bold” FontSize=”10″ H NMR (400MHz, CDCb) delta 4.09 (s, 3H). 13CNMR (400MHz, CDCb) delta 123.03, 113.09, 37.00. The filtrate was concentrated under vacuum to afford an oil, isopropanol (1 L) was added and resulting solution was warmed to 50 ¡ãC and then water (3 L) was added dropwise. The mixture was cooled to 25¡ãC and stirred for 5 hours and the resulting precipitate was collected by filtration, washed with water (300 mL x 2) and, dried under vacuum at 50¡ãC for 16 hours to afford 4,5-dibromo-2- methyl-2H-l,2,3-triazole (Intermediate 14e; 570 g, 60.8percent yield) as a solid. FontWeight=”Bold” FontSize=”10″ H NMR (400MHz, CDCb) delta 4.18 (s, 3H). 13C NMR (400MHz, CDCb) delta 124.25, 43.07.

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; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; FERON, James, Lyman; (80 pag.)WO2017/80980; (2017); A1;,
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. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-(1,2,4-Triazol-1-yl)aniline

To a solution of formamidine from Step 4 (429mg, 1.045mmol) in acetic acid (3ml) was added the 4-triazolylaniline (184mg, 1.15mmol). The reaction was heated to 1250C for Ih. The mixture was cooled down basified with 15ml of 2N NaOH and the resulting precipitate isolated by filtration then dissolved in DCM and purified by column chromatography on silica with DCM / EtOH / NH3 400:8:1 up to 50:8:1 to give after concentration a cream solid (136mg, 25%). LC-MS rt 2.1 m/z 526 ES+.1H NMR (D6-DMSO) delta 10.06 (IH, broad s), 9.29 (IH, s), 8.82 (IH, s), 8.65 (IH, s) 8.21 (2H, m), 8.07 (2H, m), 7.83(4H, m), 7.69 (IH, d, J 10Hz), 7.32 (IH, dd, J 10Hz, 5Hz), 4.17 (2H, t, J 7.5Hz), 3.58 (4H, t, J 2.5Hz), 3.34 (2H, m, obscured by H2O), 2.40 (4H, t, J 2.5Hz), 1.92 (2H, t, J 7.5Hz).

The synthetic route of 6523-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); 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. 942060-54-0, name is 4-Bromo-2,5-dimethyl-2H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Bromo-2,5-dimethyl-2H-1,2,3-triazole

A solution of 4-bromo-2,5-dimethyl-triazole (107 mg, 0.611 mmol), 4-[7-tert-butyl-5-(4- chloro-3-fluoro-phenyl)furo[3,2-b]pyridine-2-carbonyl]-3,3-dimethyl-piperazin-2-one (200 mg, 0.4368 mmol) (Intermediate I) and K3P04 (185 mg, 0.873 mmol) in DMF (2.2 mL) is charged in a sealed 4 mL vial, flushed with nitrogen, added iodocopper (87.3 mg, 0.459 mmol) and N,N’-dimethylethane-1,2-diamine (46 mg, 55 iL, 0.524 mmol), and is flushed once more with nitrogen. The reaction is stirred at 100 C for three hours. The mixture is then filtered and purified using reverse phase prep. HPLC to afford 4-[7-tert-butyl-5-(4-chloro-3-fluoro- phenyl)furo[3,2-b]pyridine-2-carbonyl]-1-(2,5-dimethyltriazol-4-yl)-3,3-dimethyl-piperazin-2-one (110 mg, 45%). 1H NMR (400 MHz, DMSO-d6) 6 8.15 (dd, J = 11.0, 2.1 Hz, 1H), 8.07 – 7.97 (m, 1H), 7.82 (s, 1H), 7.72 – 7.66 (m, 1H), 7.63 (s, 1H), 4.02 (s, 5H), 3.92 (d, J = 5.2 Hz, 2H), 2.04 (s, 3H), 1.80 (s, 6H), 1.50 (s, 9H). ESI-MS m/z calc. 552.2052, found 554.64 (M+1)+; Retention time:4.29 minutes, Method J.

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 942060-54-0.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LIU, Bingcan; DORICH, Stephane; DE LESELEUC, Mylene; DUPONT-GAUDET, Kristina; JAMES, Clint, Alwyn; VAILLANCOURT, Louis; BEAULIEU, Marc-Andre; STURINO, Claudio; (236 pag.)WO2018/57588; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 13423-60-4,Some common heterocyclic compound, 13423-60-4, name is 1-Phenyl-1H-1,2,4-triazole, molecular formula is C8H7N3, 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: Solutions of 3.0 mmol of 3-methylindole (for the synthesis of 10a-d) and 4.0 mmol of 3-methylpyrrolo[2,3-b]pyridine (for thesynthesis of 19a-d), respectively, in 10 mL of dioxane or acetonewere treated under an inert atmosphere with 5.3 mmol (10a-d) or4.0 mmol (19a-d) of the imidazoles 9aed, or 5.3 mmol of 1-phenyl-1,2,4-triazole (23). Then the solutions were cooled to12-15 C and 4.4 mmol of N-bromosuccinimide (NBS) was added portionwise within 5 min. After stirring over a period of 30 min theimidazolium salts were filtered off (10aed) or precipitated by additionof a mixture of ethanol and diethyl ether (19a-d). The products were obtained as colorless to slightly yellow solids.

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-1,2,4-triazole, its application will become more common.

Reference:
Article; Pidlypnyi, Nazar; Wolf, Sebastian; Liu, Ming; Rissanen, Kari; Nieger, Martin; Schmidt, Andreas; Tetrahedron; vol. 70; 45; (2014); p. 8672 – 8680;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 15988-11-1, These common heterocyclic compound, 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, 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: General procedure for the synthesis oftriazolo[1,2-a]indazole-trione (1a-g) and2H-indazolo[2,1-b]phthalazine-triones (2a-g)To a well-ground mixture of arylaldehyde (1 mmol), dimedone(0.140 g, 1 mmol) and 4-phenylurazole (0.177 g, 1 mmol) or2,3-dihydrophthalazine-1,4-dione (0.162 g, 1 mmol), was added[Et3N-SO3H]HSO4[(0.028 g, 0.1 mmol) for the preparation of1a-gor (0.042 g, 0.15 mmol] for the synthesis of2a-g}. Theobtained mixture was firstly stirred magnetically at 90C, andafter solidification of the reaction mixture, it was stirred with asmall rod at same temperature. After the reaction was completed(as observed by TLC), the reaction mixture was cooled to roomtemperature, water (2 mL) was added, stirred for 3 min, andfiltered. The solid residue was recrystallized from EtOH/H2O(4/1) to give the pure product.

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

Reference:
Article; Zare, Abdolkarim; Masihpour, Fatemeh; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 8; (2016); p. 1160 – 1165;,
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. 138479-53-5, name is 2-[1,2,4]Triazol-1-yl-benzaldehyde belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-[1,2,4]Triazol-1-yl-benzaldehyde

A reaction mixture of 4-(2-amino-pyrimidin-5-yl)-N1-(l, l-dimethyl-propyl)-benzene-l,2- diamine (130 mg, 0.48 mmol), 2- 1,2,4-triazol- l-yl-benzaldehyde (110 mg, 0.64 mmol) and L-proline (5 mg) in MeOH (25 mL) is refluxed for 16 hours. The reaction mixture is allowed to cool to room temperature and is concentrated under reduced pressure. The residue is purified by silica gel flash column chromatography with 8% MeOH in CH2C12 as the eluent to afford 5-[l-(l, l-dimethyl-propyl)-2-(2-l,2,4-triazol- l-yl-phenyl)-lH- benzimidazol-5-yl]-pyrimidin-2-ylamine. LCMS (ESMS): m/z 425.20 (M++l)

The synthetic route of 138479-53-5 has been constantly updated, and we look forward to future research findings.

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

Reference of 61-82-5,Some common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-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.

General procedure: A mixture of 3-amino-1,2,4-triazole or benzimidazole (1.0 mmol), benzaldehyde (1.0 mmol), dimedone (1.0 mmol), and acetonitrile (5 mL) was taken in a round bottom flask and added iodine (10 mol %) and stirred at 80 C for 10 min. After completion of the reaction, as monitored by TLC, the reaction mass was cooled to room temperature and the solid separated was filtered and washed with water and dried at reduced pressure.Data of representative examples

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-1,2,4-Triazol-5-amine, its application will become more common.

Reference:
Article; Puligoundla, Ravinder Goud; Karnakanti, Shuklachary; Bantu, Rajashaker; Nagaiah, Kommu; Kondra, Sudhakar Babu; Nagarapu, Lingaiah; Tetrahedron Letters; vol. 54; 20; (2013); p. 2480 – 2483;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7411-23-6,Some common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, 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 2 3,5-Dibromo-l-(2-methylallyl)-lH-l,2,4-triazole 3,5-Dibromo-lH-l,2,4-triazole (1.5 g, 6.61 mmol) in DMF (13 mL) was treated with sodium tert- pentoxide (0.728 g, 6.61 mmol) and the mixture was stirred for 10 min at rt under nitrogen atmosphere. 3-Bromo-2-methylprop-l-ene (0.667 mL, 6.61 mmol) was added and the mixture was stirred at 40C for 2 hours. The mixture was poured onto water and extracted with diisopropylether (2x). The organic phase was washed with water (2x), brine and dried (sodium sulfate). The solvents were evaporated to give the title compound as a liquid (1.70 g, 91%). GCMS (CI) m/z 281 [M+]. XH NMR (400 MHz, CDCI3) delta ppm 1.74 (d, 3 H) 4.69 (s, 2 H) 4.81 – 4.86 (m, 1 H) 5.05 (dd, 1 H).

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTURUM LIFE SCIENCE AB; BESIDSKI, Yevgeni; YNGVE, Ulrika; PAULSEN, Kim; LINDE, Christian; NORDVALL, Gunnar; MACSARI, Istvan; MALMBORG, Jonas; WO2014/195321; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics