Day: May 24, 2021

Electric Literature of 16681-70-2, A common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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.

1,2,3-Triazole-4-carboxylic acid (14 mg, 124 mumol), DIPEA (86.3 muL, 496 mumol) and HATU (47.1 mg, 124 mumol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester (57.2 mg, 124 mumol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product purified by preparative HPLC and lyophilized to yield the title compound (19 mg; purity 95%). MS m/z [M+H]+ calc’d for C31H32N4O6, 557.23. found 557.2.

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products 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.

[00302] To a solution of N1 -(2-chloro-6-phenylpyrimidin-4-yl)cyclohexane- 1,3 -diamine (65 mg, 0.21 mmol) in a mixed solvent of tetrahydrofuran (4 mL) and dimethyl sulfoxide (1 mL) were added N,N-diisopropylethylamine (0.11 mL, 0.7 mmol) and 1H-1,2,3-triazole-4-carboxylic acid (48 mg, 0.42 mmol). The mixture was stirred at rt for 10 mm, then HATU (163 mg, 0.43 mmol) was added, and the resulting mixture was stirred at rt for 3 hours. To the reaction mixture was added water (10 mL), and the resulting mixture was extracted with ethyl acetate (10 mL x 3). The combined organic layers were washed with saturated brine (30 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound as a colorless solid (85 mg, 100%).MS (ESI, pos.ion) m/z: 398.5 [M+H].

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; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); 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. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C4H5N3O2

EXAMPLES; Synthesis of the methyl ester of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid (triacetylribavirin, 3-carbomethoxy, TARC, IV, PG=CH3CO, R2=COOCH3); In a 6000 ml, 4-neck anhydrous reactor equipped with thermometer, condenser and mechanical stirrer, there are placed, while stirring and with a flow of nitrogen, 1680 ml of dichloromethane, 400 g of tetra-acetylribose (Fluka) and 185.2 g of 3-carbomethoxytriazole. The mixture is cooled to about 5°C and 360 g of tin tetrachloride are added to the suspension in a thin stream while stirring. The exothermy of the reaction is controlled by cooling with an ice bath so that the temperature does not exceed 15-20°C and, when the addition is finished, the reaction mixture is heated to reflux for 2 hours. It is cooled to 20°C with a water and ice bath in 15 minutes. Then 30percent hydrochloric acid (176.7 ml) and water (1503.3 ml) are added at a temperature below +20°C and stirring is carried out for 45 minutes; the mixture is left to dephase for 15 minutes, then the upper aqueous phase is separated from the rich organic phase which is subsequently treated with 30percent hydrochloric acid (176.7 ml) and water (1503.3 ml). After 45 minutes’ stirring, the mixture is left to dephase for 15 minutes and the upper aqueous phase is separated from the rich organic phase, which is subsequently treated with 30percent hydrochloric acid (176.7 ml) and water (1503.3 ml). After 45 minutes’ stirring, the mixture is left to dephase for 15 minutes and the phases are separated: the organic phase is distilled at atmospheric pressure (internal T approx. 45°C), and to the oily residue 3000 ml of toluene are added and the mixture is distilled under vacuum at about 200 mbar of residual pressure to a stirrable moist paste. It is cooled to 5-10°C for 2 hours and filtered over a Buchner filter while washing with toluene. 524 g of moist product are obtained, equal to 392 g dry product.

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:
Patent; Clariant Life Science Molecules (Italia) SpA; EP1281715; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, 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. Formula: C3H4N4O2

3-Amino-1 ,2,4-triazole-5-carboxylic acid hydrate (2.56 g, 0.02 mol) was dissolved in IMS (40 ml). Triethylamine (6 ml) was added and the solution was heated to 70C. After 10 minutes 4-cyanobenzaldehyde (2.62 g, 0.02 mol) and ethyl acetoacetate (2.60 g, 0.02 mol) were added and the reaction was heated at 70C for 24 hours. The mixture was filtered hot and allowed to cool. The volatiles were evaporated and the residue was partitioned between in ethyl acetate and 1 N HCI. A solid precipitated and was filtered off. The organic layer was separated, washed with water and then brine, dried (Na2S04), and evaporated. The residue was triturated with ethyl acetate. The solid material was combined with that which was collected earlier.Yield: 2.18 mg (31 %)LC-MS (Method 1 ): Rt = 2.69 min, m/z = 354 [M+H]+

The synthetic route of 3641-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PULMAGEN THERAPEUTICS (INFLAMMATION) LIMITED; EDWARDS, Christine; KULAGOWSKI, Janusz; FINCH, Harry; WO2011/110859; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 3179-31-5,Some common heterocyclic compound, 3179-31-5, name is 1H-1,2,4-Triazole-3-thiol, molecular formula is C2H3N3S, 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.

Example 28 2,4-Difluoro-alpha-{[(1,2,4-triazol-3-yl)sulfanyl]methyl}-3-methoxy-beta-[(quinolin-5-yl)amino)-alpha-(trifluoromethyl)benzeneethanol 200 mg(0.47 mmmol) {[2,4-difluoro-3-methoxyphenyl][2-(trifluoromethyl)oxiranyl] methyl}-2-methylquinolin-5-amine (example 9) are dissolved in 2.0 ml DMF. 307 mg (0.94 mmol) Caesium carbonate are added followed by 190 mg (1.89 mmol) 3-mercapto-1,2,4-triazole. The mixture is vigorously stirred at ambient temperature for 4 hours. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is washed with water and brine and evaporated. Flash chromatography on silica gel (acetone in hexane 10% to 50%) yields 66 mg of the title compound as one single diastereomer. 1H-NMR (DMSO d6); delta = 2.57 (s, 3H), 3.35 (d, 1 H), 3.67 (d, 1H), 3.81 (s, 3H), 5.31 (d, 1H), 6.29 (d, 1H), 6.33 (d, 1 H), 7.06 (dd, 1 H), 7.14 (d, 1H), 7.35 (d, 1H), 7.36 (t, 1H), 8.38 (s, 1H), 8.45 (d, 1 H).

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-Triazole-3-thiol, its application will become more common.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; AstraZeneca AB; EP1878717; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1455-77-2, These common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-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.

General procedure: An equimolar solution of 3,5-diamino-1,2,4-triazole (0.99 g, 0.01 mol) and 2-hydroxynaphthaldehyde (1.72 g, 0.01 mol) in dry methanol (50 mL) was refluxed for 3 h, a precipitated product was formed during refluxing. It was then cooled to room temperature, filtered, washed with methanol (35 mL), then with diethyl ether (2 × 5 mL) and dried under vacuum. Recrystallization in a mixture of methanol:dioxane (1:4) gave TLC pure product (L1) in 83percent yield. The same method was applied for the preparation of all other ligands (L2)?(L5).

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

Reference:
Article; Sumrra, Sajjad H.; Chohan, Zahid H.; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 98; (2012); p. 53 – 61;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 23579-79-5,Some common heterocyclic compound, 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, molecular formula is C3H3Br2N3, 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.

In a 50 mL pressure vial, 3,5-dibromo-1-methyl-1H-1,2,4-triazole (Int-41, 1.42 g, 5.89 mmol) was dissolved in DMF (12 mL) and potassium carbonate (1.36 mg, 9.82 mmol), followed by 3- chloro-5-methylphenol (700 mg, 4.91 mmol) were added. The vial was sealed, the reaction mixture was stirred for 15 h at 100 C. After cooling, it was concentrated in vacuo, the residue was purified by column chromatography (silica gel, 70 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 25:75 v/v) to yield the title compound as white solid (1.37 g, 92%). 1H NMR (CDC13, 300 MHz): delta 2.37 (s, 3 H), 3.77 (s, 3 H), 6.99-7.02 (m, 1 H), 7.06-7.08 (m, 1 H), 7.11- 7.14 (m, 1 H). MS (ES+) m/z 302.0, 304.0, 306.0 [M+H, Br & CI isotopes] .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7411-23-6, name is 3,5-Dibromo-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 7411-23-6, Product Details of 7411-23-6

In a 100 mL round bottomed flask, 3,5-dibromo-1H-1,2,4-triazole (Int-1, 500.0 mg, 2.2 mmol) was dissolved in DMF (32 mL) and the solution was cooled to 0-5 C (ice bath). Sodium hydride (55% dispersion in mineral oil, 106 mg, 2.64 mmol) was added in portions and the resulting mixture was stirred for 5 min at 0-5 C and for 15 min at room temperature. After that, 2-methoxyethyl methanesulfonate (815.5 mg, 5.29 mmol) was added dropwise at room temperature. The resulting mixture was stirred for 15 h at room temperature. After that, it was diluted with ethyl acetate (20 mL) and water (20 mL), the aqueous phase was extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo, the residue was purified by column chromatography (silica gel, 30 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 20:80 v/v) to yield the title compound as colorless oil (362 mg, 58%). 1H NMR (CDC13, 300 MHz): 3.33 (s, 3 H), 3.76 (t, J = 5.3 Hz, 2 H), 4.29 (t, J = 5.3 Hz, 2 H). MS (ES+) m/z 285.8.

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, 3,5-Dibromo-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); 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. 40253-47-2, name is Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C6H9N3O2

To a mixture of ethyl 5-methyl-1 H-1 ,2,4-triazole-3-carboxylate (200 mg, 1 .29 mmol) in THF (5 mL) was added LiAIH4(245 mg, 6.45 mmol) at 0C under N2. The mixture was stirred at 30C for 1 hour. The mixture was filtrated and washed with methanol, concentrated in vacuo to give(5-methyl-1 H-1 ,2,4-triazol-3-yl)methanol (350 mg).

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:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (270 pag.)WO2018/7249; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7343-33-1, name is 5-Bromo-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 7343-33-1, name: 5-Bromo-1H-1,2,4-triazole

To a reaction vial were added 2-bromo-5-(trifluoromethoxy)pyridine ( 1.0 g, 4.1 mmol) and 3-bromo- l – -l,2,4-triazole (0.91 g, 6.2 mmol). Lambda ,/V-Dimethylformamide (16 ml_) and cesium carbonate (2.6 g, 8.2 mmol) were added, and the vial was degassed for 5 minutes with argon. Copper(I) iodide (0.077 g, 0.41 mmol) was added, and the via l was further degassed for 5 minutes with argon. The vial was capped and heated at 100 C for 1 hour in a Biotage Initiator microwave reactor, with external IR-sensor temperature monitoring from the side of the vessel. The reaction mixture was cooled to room temperature, poured onto crushed ice (3 volumes), and extracted with ethyl acetate (3 x 150 ml_). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography using 0-40% ethyl acetate/hexanes as eluent provided the title compound as a pale brown liquid (0.40 g, 31%) : *H N MR (400 MHz, CDCI3) delta 9.01 (s, 1H), 8.39 (d, J = 2.4 Hz, 1H), 7.94 (d, J = 8.8 Hz, 1H), 7.77 (dd, J = 1.6 Hz, 8.8Hz, 1H) ; ESIMS m/z 309 ([M + H]+).

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

Reference:
Patent; DOW AGROSCIENCES LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; SPARKS, Thomas C.; DEMETER, David A.; (242 pag.)WO2017/40742; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics