Category: Triazoles

Related Products of 27996-86-7,Some common heterocyclic compound, 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, molecular formula is C9H7N3O, 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: The general procedure for the synthesis of the N-heterocycles using SnAP reagents was as follows. To a solution of the aminotributylstannane-SnAP reagent (0.50 mmol, 1.00 equiv.) in CH2Cl2 (2.5 ml) was added the corresponding aldehyde (0.50 mmol, 1.00 equiv.) and molecular sieve (MS) 4A (50 mg) under an inertat mosphere at r.t. The reaction mixture was stirred for two hours and filtered through a layer of Celite (0.3 cm), rinsing with CH2Cl2. The filtrate was concentrated under reduced pressure to afford the imine. Separately, anhydrous Cu(OTf)2 (0.50 mmol, 1.00 equiv.) was added to as olution of 2,6-lutidine (0.50 mmol, 1.00 equiv.) in HFIP (2.0 ml) in a dry Schlenk flask and stirred at r.t. for one hour, during which a homogeneous suspension formed. A solution of the imine (0.50 mmol, 1.00 equiv.) in dry CH2Cl2 (8.0 ml) was added in one portion and the resulting mixture was allowed to stir at r.t. for 12 hours (unoptimized reaction time). The reaction was quenched at r.t. with a mixture ofsaturated aqueous NaHCO3 (4 ml) and 10% aqueous NH4OH (2 ml). The mixturewas stirred vigorously for 15 minutes, the layers were separated and the aqueous layer was extracted with CH2Cl2 (3 × 5 ml). The combined organic layers were washed with H2O (3 ×5 ml) and brine (10 ml), dried over Na2SO4, filtered, concentrated and purified by flash column chromatography on silica gel using a precolumn of KF (3 cm).

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

Reference:
Article; Vo, Cam-Van T.; Luescher, Michael U.; Bode, Jeffrey W.; Nature Chemistry; vol. 6; 4; (2014); p. 310 – 314;,
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. 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Formula: C3H5N3

Into a macrowave tube, 4-methyl-1 H-1 ,2,3-triazole (473 mg, 5.69 mmol) was dissolved in THF (10 ml) and cooled to 0C, NaH (341 mg, 8.54 mmol) was added and stirred for 1 h at rt. A solution of 4-(4-methoxyphenyl)butyl methanesulfonate (490 mg, 1.897 mmol) in DMF (2.00 ml) and THF (1.0 ml) was then added and heated to 60C for 3h. The mixture was diluted with EA (20 ml) and filtered through a pad of celite. The filtrate was concentrated to dryness. The crude was purified using ISCO column (DCM to 40% EA in DCM) to give two isomers. The title compound (0.13 g), 1H NMR (400 MHz, CDCb) delta ppm 1.57 – 1.64 (m, 2 H) 1.88 – 2.02 (m, 2 H) 2.29 (s, 2 H) 2.57 (t, J=7.63 Hz, 2 H) 3.78 (s, 3 H) 4.35 (t, J=7.04 Hz, 2 H) 6.76 – 6.86 (m, 2 H) 7.06 (m, J=8.22 Hz, 2 H) 7.31 (s, 1 H) and 2-(4-(4-methoxyphenyl)butyl)-4-methyl-2H-1 ,2,3-triazole (0.18 g). 1H NMR (400 MHz, CDCb) delta ppm 1.60 – 1.68 (m, 2 H) 1.80 – 1.97 (m, 2 H) 2.26 (s, 1 H) 2.33 (s, 2 H) 2.52 – 2.66 (m, 2 H) 3.78 (s, 3 H) 4.16 – 4.36 (m, 2 H) 6.82 (m, J=8.22 Hz, 2 H) 7.05 (d, J=8.61 Hz, 2 H) 7.32 (m, 1 H)

The synthetic route of 27808-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; GAREAU, Yves; GINGRAS, Stephane; CHANTIGNY, Yves; YANG, Gaoqiang; SAUVAGEAU, Guy; BACCELLI, Irene; MARINIER, Anne; (284 pag.)WO2019/84662; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7411-23-6, 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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

Triethylamine (2.0 mL, 14.5 mmol) was slowly added to a solution of 3,5-dibromo-1H-1,2,4-triazole (1.1 g, 4.83 mmol), 2-[tert- butoxycarbonyl(methyl)amino]ethyl methanesulfonate (1467 mg, 5.8 mmol) in DMF (22 mL). The reaction mixture was them stirred at 65 oC for 18 h. The reaction mixture was quenched with NH4Cl (sat. aq.) and extracted with DCM. The combined organic fractions were dried with a phase separator and reduced in vacuo. The residue was dissolved in DCM and reduced onto silica. Purification by silica column chromatography eluting with 0-5% MeOH inDCM afforded 2-(3,5-dibromo-1,2,4-triazol-1-yl)-N-methyl-ethanamine (644 mg, 2.27 mmol, 47% yield) as an orange liquid. UPLC-MS (ES+, Method A): 1.70 min, m/z 283.9 [M+H]+.

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

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Product Details of 16681-65-5

Intermediate 13: bis(1-methyl-1H-1,2,3-triazol-5-yl)methanoneA solution of 1 -methyl- lH-1, 2, 3-triazole (0.954 g, 11.4 mmol, prepared according to PCX Int. AppL, 2008098104) in THF (22 mL) was stirred at-70 C under argon while -BuLi (2.56 M in hexanes, 4.29 mL, 11.0 mmol) was added dropwise over 5 minutes. After stirring for another 5 minutes, a solution of ethyl mefhoxy(methyl)carbamate (0.665 g, 4.99 mmol) in THF (3 mL) wras added dropwise over 5 minutes. After stirring at ~-70 C for an additional 5 minutes, the cold bath was removed and the light slurry was allowed to warm to room temperature with stirring for 1 hour 20 minutes. The reaction was then quenched at room temperature with 5 M aqueous H4CI (3 mL) and the aqueous layer was extracted with THF (1 x 6 mL). The combined organic layers were dried (Na2S04), filtered, and concentrated. A portion of the residue was crystallized from -’30 mL toluene to provide, after washing the filter cake with ether (1 > 3 mL) and heptane (1 x 3 mL), to yield the title compound as blunt needles.

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; JANSSEN PHARMACEUTICA NV; 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.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 6523-49-5, These common heterocyclic compound, 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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.

A mixture of formamidine from Step 1 (150 mg) and 4-triazolyl-aniline (88 mg, leq) in AcOH (2ml) was heated to 80 for 16 h. Cooled, concentrated and cautiously treated with sodium bicarbonate (aq). The resulting solid was isolated by filtration, washed with water then DCM:EtOH:NH3 (20:8:1) added and refiltered. The filtrate was concentrated until a precipitate formed which was filtered, washed with ether and dried to give the title compound (82 mg, 34 %). 1U NMR delta 10.0 (IH, s), 9.18 (IH, s), 8.75 (IH, s), 8.54 (IH, s), 8.12 (2H, m),7.97 (IH, m), 7.92 (2H, m), 7.78 (3H, m), 7.66 (IH, m), 7.53 (IH, m); LC-MS rt 2.52 m/z 401 ES+.

Statistics shows that 4-(1,2,4-Triazol-1-yl)aniline is playing an increasingly important role. we look forward to future research findings about 6523-49-5.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 217448-86-7, 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. 217448-86-7, name is Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A 250 mL two-necked round bottomflask was charged with sodium azide (6.10 g, 93.8 mmol), compound2 (1.90 g, 6.84 mmol), and water (20 mL). After the solidwas completely dissolved, compound 1a (5.0 g, 31.37 mmol) andCH3CN (80 mL) were added. The mixture was stirred at room temperaturefor 3 h, and then the CH3CN layer was separated. To theCH3CN solution were added Cu2O-NP (0.42 g) and compound 4(2.80 mL, 31.3 mmol), and the reaction mixture was stirred for8 h at room temperature under protection of inert gas. The mixturewas filtered and the filtrate was concentrated, and was chargedwith methanol (40 mL) and 35% ammonia in water (100 mL). The mixture was heated to 65 C and refluxed for 4 h, cooled to roomtemperature, and filtered. The resulting solid was washed withwater and methanol to obtain rufinamide (5.25 g, 71.6%) as colorlesscrystalline product. Mp: 242-244 C. 1H NMR (400 MHz,DMSO-d6) d 8.549 (s, 1H), 7.842 (br s, 1H), 7.566-7.470 (m, 2H),7.215-7.174 (m, 2H), 5.723 (s, 2H). 13C NMR (100 MHz, DMSOd6)d 162.5, 161.7, 160.0, 143.3, 132.3, 127.4, 112.4, 111.5, 41.66.MS (ESI+): 239.06.

The chemical industry reduces the impact on the environment during synthesis Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Jing-Han; Pan, Cheng-Wen; Li, Yong-Tao; Meng, Fan-Fei; Zhou, Hong-Gang; Yang, Cheng; Zhang, Quan; Bai, Cui-Gai; Chen, Yue; Tetrahedron Letters; vol. 54; 26; (2013); p. 3406 – 3409;,
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. 138624-97-2, name is 1-Benzyl-1H-1,2,4-triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9N3O2

A mixture of 1-benzyl-1H-1,2,4-triazole-3-carboxylic acid (32 mg, 0.16 mmol), 1-(3- dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (28 mg, 0.14 mmol), 3-amino-i – methyl-4,5-dihydro-3h-pyrido [1,2-a] [1,3] diazepine-2,7-dione (25 mg, 0.12 mmol) and 1- hydroxybenzotriazole (20 mg, 0.14 mmol) in N,N-dimethylformamide (3 mL) was stuffed at 25 C for 12 h. The mixture was concentrated to dryness under reduce pressure. The resultingresidue was purified by reverse phase chromatography (acetonitrile 10-40% / 0.05% ammonia hydroxide in water) to afford 1 -benzyl-N-( 1 -methyl-2,7-dioxo- 1,2,3,4,5,7- hexahydropyrido [1,2-a] [1,3] diazepin-3-yl)- 1 H-i ,2,4-triazole-3-carboxamide (30 mg, 63%) as a white solid. The racemic material was further purified by SFC to give arbitrarily assigned:1 -benzyl-N-[(3S)- 1 -methyl-2,7-dioxo-4,5-dihydro-3H-pyrido[ 1,2-a] [1 ,3]diazepin-3-yl]-1,2,4-triazole-3-carboxamide (Peak 1, retention time = 5.180 mm) (12 mg, 40%) as white solids. ?H NMR (400 MHz, CD3OD) 5 8.57 (s, 1H), 7.64 – 7.56 (m, 1H), 7.47 – 7.25 (m, 5H), 6.53 (d, J = 9.2 Hz, 1H), 6.46 (d, J = 7.2 Hz, 1H), 5.47 (s, 2H), 5.07 – 5.03 (m, 1H),4.61 – 4.55 (m, 1H), 3.71 – 3.63 (m, 1H), 3.39 (s, 3H), 2.68 – 2.60 (m, 1H), 2.19 – 2.12 (m, 1H). LC-MS RT = 1.177 mm, mlz = 393.2 [M+H]. LCMS (10 to 80% acetonitrile in water +0.03% ammonium bicarbonate over 3.0 mins) retention time 1.177 mm, ESI+ found [M+H] =393.2.1 -benzyl-N- [(3R)- 1 -methyl-2,7-dioxo-4,5-dihydro-3H-pyrido [1,2-a] [1,3] diazepin-3-yl]-1,2,4-triazole-3-carboxamide. (Peak 2, retention time = 6.616 mm) (8 mg, 26%) as white solids. ?H NMR (400 MHz, CD3OD) (5 8.56 (s, 1H), 7.63 – 7.57 (m, 1H), 7.43 – 7.25 (m, 5H), 6.52 (d, J = 9.2 Hz, 1H), 6.45 (d, J = 7.2 Hz, 1H), 5.47 (s, 2H), 5.06 – 5.01 (m, 1H),4.59 – 4.56 (m, 1H), 3.69 – 3.62 (m, 1H), 3.39 (s, 3H), 2.68 – 2.60 (m, 1H), 2.19 – 2.12 (m, 1H). LC-MS RT = 1.179 mi mlz = 393.1 [M+Hf?. LCMS (10 to 80% acetonitrile in water +0.03% ammonium bicarbonate over 3.0 mins) retention time 1.179 mi ESI+ found [M+H] =393.1.SFC condition: column: chiralcel OD-3 100 x 4.6mm I.D., 3um mobile phase:A:C02 B: ethanol (0.05% DEA) gradient: hold 5% for 1.0 mm, then from 5% to 40% of B in 4.5 mm and hold 40% for 2.5 mm, then 5% of B for 1.0 mm. Flow rate: 2.8 mL/min. Columntemperature: 40 C.

The synthetic route of 138624-97-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; (105 pag.)WO2018/73193; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 81606-79-3, These common heterocyclic compound, 81606-79-3, name is 2-(1,2,4-Triazol-1-yl)acetonitrile, 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.

To a 25 ml microwave vial, N-((2S,3R)-l -(((S)-l -((2-fluoro-4-methylbenzyl)amino)-3- (3-formylphenoxy)-l-oxopropan-2-yl)amino)-3-hydroxy- l-oxobutan-2-yl)-5-methylisoxazole-3- carboxamide (190 mg, 0.46 mmol) and 2-(l H-l ,2,4-triazol- l -yl)acetonitrile (247 mg, 2.28 mmol) were suspended in toluene (2 ml). TEA (0.15 ml, 1.05 mmol) was added and stirred at 125 C for 1 .5 h in microwave. The reaction mixture was diluted with cold water and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated to get the crude product which was purified by prep HPLC purification using 0.1 % Formic Acid in water as modifier in acetonitrile to yield 16 mg of N-((2S,3R)-l -(((S)-3-(3-(2- cyano-2-(l H- l ,2,4-triazol-l -yl)vinyl)phenoxy)-l -((2-fluoro-4-methyl benzyl)amino)-l – oxopropan-2-yl)am i no)-3 -hydroxy- 1 -oxobutan-2-yl)-5 -methyl i soxazole-3 -carboxam ide. LC-M S (ES, m/z): 631 [M+H].

The synthetic route of 81606-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRAMELD Kenneth; OWENS Timothy; WO2015/195950; A1; (2015);,
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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C3H3N3O2

[0683] Compound 3b (7.0 mg, 16 f.tmol) was combinedwithDMF (0.5 mL), lH-1,2,3-triazole-5-carboxylic acid (2.0mg, 18 f.tmol), HATU (6.8 mg, 18 flillOl) and DIPEA (8.5 f.LL,49 f.tmol). The mixture was stirred for 30 minutes after whichtime LCMS showed the desired product formation. The solutionwas concentrated in vacuo to yield Compound 4b whichwas used directly in the next step.

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.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 584-13-4,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.

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 4H-1,2,4-Triazol-4-amine, 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