Category: Triazoles

Electric Literature of 81606-79-3, 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. 81606-79-3, name is 2-(1,2,4-Triazol-1-yl)acetonitrile belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

Step 1To a 50 ml three necked round bottom flask, 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)- methyl)-5H-pyrrolo[2,3-b]pyrazine-2-ylamino)benzaldehyde (O.lg, 0.22 mmole) and 2-(lH- l,2,4-triazol-l-yl)acetonitrile(0.0716g, 0.66 mmole) was taken in ethanol (5 mL). To this reaction mixture, piperidine (0.2 mL) was added drop wise at RT. After completion of the addition, the reaction mass was refluxed for 16 hrs and the completion of the reaction was monitored on TLC using ethyl acetate: hexane (5:5) as a mobile phase. After completion of the reaction, ethanol was distilled out and water was added to residue. Aqeous was extracted with ethyl acetate, organic layers were combined, dried over Na2S04, filtered and concentrated to afford crude product. The crude compound was purified using column purification by eluting the compound with 40% ethyl acetate in hexanes triturated with n-pentane, pentane layer was decanted and solid was dried under vacuum to yield 0.052 g of 3-(4-(7-pivaloyl-5-((2- (trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)-2-(lH-l,2,4-triazol- 1 -yl)acrylonitrile.

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, 2-(1,2,4-Triazol-1-yl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; VERNER, Erik; WO2012/158785; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 815588-93-3, name is 1-Methyl-1H-1,2,4-triazole-5-carboxylic acid, 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 815588-93-3, HPLC of Formula: C4H5N3O2

[00178] To a stirring solution of Int-C (93 mg, 0.73 mmol) in DCM (20 mL) were added N, N-diisopropylethylamine (0.4 mL, 2.21 mmol), compound 7 (320 mg, 0.73 mmol), followed by EDCI.HC1 (211 mg, 1.10 mmol), HOBt (170 mg, 1.10 mmol) at 0 ¡ãC and stirred at RT for 16 h. After consumption of the starting material (by TLC), the reaction mixture was evaporated under reduced pressure and the obtained crude was purified by column chromatography by eluting 4percent MeOH/DCM to afford 8 (210 mg, crude) as yellow thick syrup. This compound was used directly for next step without any purification. LCMS m/z: 543.5 [M++l]

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; NAUREX, INC.; LOWE, John, A.; KHAN, M., Amin; WO2014/120800; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

(25,,^5)-4-Amino-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-cyanomethylpentanoic acid ethyl ester (55 mg, 141 muiotaetaomicron) was combined with 3H-[l,2,3]triazole-4-carboxylic acid (19.2 mg, 170 muiotaetaomicron), HATU (64.5 mg, 170 muiotaetaomicron) and DIPEA (79 mu, 453 muiotaetaomicron) in DMF (2 mL) and was stirred at room temperature for 30 minutes then concentrated in vacuo and the crude residue was purified by normal phase chromatography (0-100% EtOAc/hexanes) to yield Compound 1 55 mg).

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

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FLEURY, Melissa; BEAUSOLIEL, Anne-Marie; HUGHES, Adam D.; LONG, Daniel D.; WILTON, Donna A.A.; WO2015/116786; (2015); 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. 118863-62-0, name is 3-(4-Bromophenyl)-1H-[1,2,4]triazole, This compound has unique chemical properties. The synthetic route is as follows., name: 3-(4-Bromophenyl)-1H-[1,2,4]triazole

Example 8 Preparation of 3-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C5) (0174) (0175) 3-(4-Bromophenyl)-1H-1,2,4-triazole (C4) (10.9 g, 48.5 mmol), copper(I) iodide (2.38 g, 12.5 mmol), and cesium carbonate (30.3 g, 93.0 mmol) in a round-bottomed flask was flushed with nitrogen. Dimethylsulfoxide (85 mL) was added, followed by 1-iodo-4-(trifluoromethoxy)benzene (13.2 g, 45.8 mmol). The reaction was degassed for 5 minutes, then heated at 100 C. for 3 days. The reaction was cooled to room temperature, diluted with ethyl acetate, and filtered through a plug of Celite rinsing with ethyl acetate. To the filtrate was added saturated ammonium chloride and stirred for 1.5 hours. The layers were separated and the aqueous layer was extracted with ethyl acetate (3¡Á). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated onto Celite. Purification by flash column chromatography using 0-40% EtOAc/hexanes as eluent provided the title compound as an off-white solid (9.65 g, 52%): mp 109-112 C.; 1H NMR (400 MHz, CDCl3) delta 8.56 (s, 1H), 8.10-8.03 (m, 2H), 7.83-7.75 (m, 2H), 7.64-7.57 (m, 2H), 7.42-7.35 (m, 2H); ESIMS m/z 386 ([M+21-1 ]+).

According to the analysis of related databases, 118863-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; Fischer, Lindsey G.; Crouse, Gary D.; Sparks, Thomas C.; Goldsmith, Miriam E.; Knueppel, Daniel I.; (66 pag.)US2016/24027; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1533519-85-5, The chemical industry reduces the impact on the environment during synthesis 1533519-85-5, name is Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, I believe this compound will play a more active role in future production and life.

In a 100 ml three-necked flask equipped with a stirrer, a thermometer, 25 ml of DMF was added, the intermediate (IV)3.39 g, stirred at room temperature, 0.42 g of sodium hydroxide was added and 1.87 g of NBS was added in portions at 25 C,Add to maintain the stirring for 3 hours; add 50ml of water, then ethyl acetate 50ml x3 extraction, combined organicThe phases were concentrated and the ethyl acetate was removed by adding 25 ml of ethyl acetate / 50 ml of n-hexane to recrystallize,To give the product 3.55 g, i.e. intermediate (V), in a yield of 84.93%.

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, Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chengdu Baoyu Pharmaceutical Co., Ltd.; Lei, Lang; Li, Shanwei; Xiong, Bo; (10 pag.)CN105906576; (2016); 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. Recommanded Product: 1H-1,2,3-Triazole

Potassium carbonate (14.0 g, 101.35 mmol) was added to solution of 2,3-dichloro-5- nitropyridine (10.0 g, 51.82 mmol) in THF (60 mL) followed by addition of 2H-1,2,3-triazole (3.4 mL, 58.7 mmol). The resulting mixture was stirred at rt until reaction was deemed completed as judged by TLC (-16 h), then diluted with water (300 mL). The aqueous layer was extracted with EtOAc (2 x 300 mL), the organic layer was dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica (100-200 mesh), eluted at 20% EtOAc in p. ether which gave the title compound (7.0 g, 60%) as a solid with 99.42% LCMS purity. MS (ES+) 226.03 [M+H]+.

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; MEDIVIR AKTIEBOLAG; ERSMARK, Karolina; KARLSTROeM, Sofia; KLASSON, Bjoern; LUNDGREN, Stina; ROSENQUIST, Asa; SALVADOR ODEN, Lourdes; (155 pag.)WO2018/226150; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, These common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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.

[0394] (2S,4S)-4-Amino-5-biphenyl-4-yl-2-methoxymethylpentanoicacid ethyl ester (16 mg, 47 fllllOI) was dissolvedin DMF (0.3 mL). 1H-1,2,3-Triazole-4-carboxylicacid (5.3 mg, 47 f.tmol) and HATU (18 mg, 47 f.tmol) wereadded followed by DIPEA (25 f.LL, 141 fllllOI). The mixturewas stirred for 30 minutes and concentrated under reducedpressure to yield Compound 1, which was used in the nextstep without purification.

Statistics shows that 1H-[1,2,3]Triazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 16681-70-2.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 956317-36-5,Some common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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.

Oxalyl chloride (14.26 g, 118.1 mmol) was added over a period of 14 minutes to a stirred suspension of 5-methyl-2-(2H-l,2,3-triazol-2-yl)benzoic Acid (20.0 g, 98.4 mmol) in CH2CI2(132 mL) and DMF (2.0 mL) at 1 C. After complete addition the reaction mixture was stirred for 30 minutes at 5 C. An addition funnel was charged with a solution of 3-((2- ((tert-butoxycarbonyl)amino)ethyl)amino)butanoate (24.4 g, 93.7 mmol) in CH2CI2(340 mL) and NEt3(19.0 g, 187.4 mmol). The amine solution was added over a period of 40 minutes to the stirred acid chloride solution at a rate to keep the internal temperature < 10 C. The reaction progress was monitored by HPLC and the reaction was judged complete after two hours. The reaction was quenched with H20 (250 mL) and the pH- value was adjusted to pH = 10.0 by the addition of NaOH (2.0 M).The organic layer was separated and washed with H20 (250 mL) at a pH = 2.0 adjusted with HC1 (2.0 M). The organic phase was concentrated under reduced pressure. The residue was taken up in toluene (100 mL) and concentrated under reduced pressure to give 49.6 g residue. The residue was taken up in cyclohexane (~ 250 mL) and stirred for two hours at room temperature. The solid was filtered, washed twice with cyclohexane (2 x 20 mL) and dried (40 C, 1H NMR (300 MHz, DMSO-D6): delta = 6.77 - 8.07 (series of overlapping m, 6H), 3.88 - 4.37 (series of overlapping m, 1H), 3.42 - 3.66 (three s, 3H), 2.56 - 3.35 (series of overlapping m, 6H), 2.39 (three s, 3H), 0.82 - 1.40 (series of overlapping m, 12H). The synthetic route of 956317-36-5 has been constantly updated, and we look forward to future research findings. Reference:
Patent; SANDOZ AG; BARTH, Roland; KAUFMANN, Marius; (97 pag.)WO2016/20404; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. Formula: C2HBr2N3

General procedure: 3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) or 3-chloro-1,2,4-triazole (300 mg, 2.9 mmol), o-quinone methide precursor 2 (2.9mmol), and K2CO3 (1.2 g, 8.7 mmol) were refluxed for 4 h in DMF (10mL). After completion of the reaction, the mixture was cooled, andpoured into H2O (30 mL). The precipitate formed was collected by filtration,washed with H2O, dried, and recrystallized.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7411-23-6, its application will become more common.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-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 16681-65-5, Recommanded Product: 1-Methyl-1H-1,2,3-triazole

To a flask containing 1-methyl-1H-1,2,3-triazole (200 mg, 2.41 mmol) was added THF (15 mL) and the solution was cooled to -45 C. using a CH3CN-CO2 bath. n-BuLi (2.5 M in hexanes, 1.0 mL, 2.5 mmol) was added dropwise which afforded an opaque white suspension. The mixture was stirred at -45 C. for 25 minutes, then a solution of (4-chloro-3-cyclopentyl-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (475 mg, 1.24 mmol, Intermediate 68: step c) in THF (3 mL) was introduced. After 10 minutes, the -45 C. bath was replaced with an ice-water bath. After 30 minutes, the reaction mixture was quenched with aqueous NH4Cl solution and extracted with EtOAc:THF (2:1, 3*40 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (3% MeOH-DCM increasing to 10% MeOH) provided the title compound as a light tan solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.24 (d, J=1.9 Hz, 1H), 7.69 (d, J=8.7 Hz, 1H), 7.35 (dd, J=8.7, 2.0 Hz, 2H), 7.07 (s, 1H), 6.01 (s, 1H), 4.07 (s, 3H), 3.90-3.80 (m, 4H containing a 3H singlet at 3.86), 3.32 (s, 3H), 2.06-1.94 (m, 3H), 1.94-1.84 (m, 6H), 1.75-1.69 (m, 2H). MS (ESI): mass calcd. for C24H27ClN6O2, 466.2. m/z found 467.1 [M+H]+. The racemate was separated by chiral SFC (Stationary phase: Chiralpak AD-H, 5 mum 250¡Á20 mm, Mobile phase: 70% CO2: 30% EtOH (0.3% iPrNH2)) to give Example 135b as the first compound that eluted from the chiral column and Example 135c as the second compound that eluted from the chiral column.

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; JOHNSON & JOHNSON; 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.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics