Triazoles

Synthetic Route of 41253-21-8,Some common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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 1.5 kg of crude alpha,alpha,alpha’,alpha’-tetramethyl-5-bromomethyl-1,3-benzene-diacetonitrile 5 (purity >80%, about 3 mol) in 7.5 l_DMF 0.275 kg 1,2,4-triazole sodium (3 mol) were added. The mixture was stirred at room temperature for 1 hr. After completion, 10 l ethyl acetate and 25 l water were added. The mixture was stirred for about 10 minutes and then phase separated. To the aqueous layer 5 l ethyl acetate were added. The mixture was stirred for about 10 minutes and then phase separated. The aqueous layer was discarded, and the organic layers were combined. The combined organic layers were washed with 10 l water twice. The organic layer was concentrated to dryness to obtain the crude anastrozole 6 (90%, purity>60%). The crude product was purified by flash column chromatography (silica) using ethyl acetate as eluent (purity>98%). Finally, the pre-purified anastrozole was re-crystallised from ethyl acetate/cyclohexane (1:2) to obtain 6 with a purity of more than 99.9%. Yield 34%.

The synthetic route of 41253-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HELM AG; US2006/217569; (2006); A1;,
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 3179-31-5 as follows. COA of Formula: C2H3N3S

2-(3-Chloromethyl-benzoylamino-4-methyl-thiophene-3-carboxylic acid ethyl ester (700 mg) obtained by the above reaction was dissolved in anhydrous methylene chloride (5.0 ml), triethylamine (580 mul) and 3-mercapto-1,2,4-triazole (compound B’) (404 mg) were added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added at room temperature, and the reaction mixture was extracted by liquid separation using chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 4-methyl-2-[3(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzoylamino]-thiophene-3-carboxylic acid ethyl ester as a useful intermediate (606 mg, yield 72%).

According to the analysis of related databases, 3179-31-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1614676; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 288-88-0, A common heterocyclic compound, 288-88-0, name is 1H-1,2,4-Triazole, molecular formula is C2H3N3, 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.

14a p-(1,2,4-Triazol-1-yl)benzaldehyde and p-(1,2,4-Triazol-4-yl)benzaldehyde 21 ml (200 mmol) of 4-fluorobenzaldehyde (Fluka, Buchs, Switzerland), 30.48 g (220 mmol) of potassium carbonate and 13.8 g (200 mmol) of 1,2,4-triazole (Fluka, Buchs, Switzerland) are suspended in 100 ml of pyridine, after which 1.2 g of copper(I) oxide are added. The reaction mixture is boiled at reflux for 16 h. After that, the solvent is removed and the residue is taken up twice in toluene, followed by evaporation, and dissolved in methylene chloride. The insoluble material is removed by filtration and the solution is concentrated. This yields a mixture of the two 1,2,4-triazol-1-yl- and 1,2,4-triazol-4-yl-substituted benzaldehyde, which can be separated, after digesting with hexane, by means of chromatography on silica gel (mobile solvent: hexane/ethyl acetate 1:1, ethyl acetate and methylene chloride/5% methanol). p-(1,2,4-Triazol-1-yl)benzaldehyde: HPLC20-100: tret=8.50. 1H NMR (DMSO-D6; 200 MHz): 10.04/s (1H); 9.47/s (1H); 8.31/s (1H); 8.12 and 8.09/in each case d, J=10 (2*2H). p-(1,2,4-Triazol-4-yl)benzaldehyde: HPLC20-100: tret=5.96. 1H NMR (DMSO-D6; 200 MHz): 10.05/s (1H); 9.27/s (1H); 8.31/s (1H); 8.09 and 7.98/in each case d, J=9 (2*2H).

The synthetic route of 288-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novatis AG; US6451973; (2002); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-70-2, 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.

lH-l,2,3-triazole-4-carboxylic acid (2.3 mg, 20 muetaiotaomicron) was combined with HATU (7.7 mg, 20 muiotaetaomicron) in DMF (2 mL) and stirred at room temperature for 15 minutes. (1383) Compound 3 (7.7 mg, 18 muiotaetaomicron) and DIPEA (9.6 mu, 55 muiotaetaomicron) were then added. The solution was stirred at room temperature for 15 minutes, at which time LCMS showed reaction completion. The solvent was removed in vacuo and the crude residue was dissolved in EtOH (2 mL). A solution of IN LiOH (183 mu^, 183 muiotaetaomicron) in water was added, and the resulting solution was stirred at room temperature for 30 minutes, at which time LCMS showed reaction completion. The solvent was removed in vacuo and the crude residue was purified by reverse phase chromatography to yield Compound a (3 mg) as a TFA salt. MS m/z [M+H]+ calc’d for C23H25CIFN5O4, 490.16; found 488.

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid 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

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. 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9N3O2

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-((iert.-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, < 5 mbar) to give the product (35.4 g, 84% yield) as a crystalline solid. 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 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; SANDOZ AG; BARTH, Roland; HOeFERL-PRANTZ, Kathrin; RICHTER, Frank; WIDSCHWENTER, Gerhard; (166 pag.)WO2016/20405; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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: C3H5N3

A solution of n-BuLi (0.73 mL, 1.8 mmol, 2.5 M solution in hexane) was added slowly to a solution of 1-methyl-1H-1,2,3-triazole (0.83 g, 10 mmol) in THF (12 mL) at -50 C. After addition, stirring was continued for an additional 30 minutes and 2-(trifluoromethyl)isonicotinaldehyde (0.350 g, 2.0 mmol) dissolved in THF (4 mL) was slowly added. An additional 2 mL of THF was used to complete the quantitative addition. The mixture was stirred at -50 C. for 5 minutes then warmed to room temperature and stirred overnight. The solution was quenched with saturated aqueous NH4Cl solution. H2O was added and layers were separated. The aqueous layer was extracted with EtOAc and the combined organic extracts washed with brine, dried over MgSO4, filtered, and evaporated in vacuo. The crude product was purified using flash column chromatography (0 to 50% EtOAc/DCM) to provide the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-65-5, its application will become more common.

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

Electric Literature of 4928-87-4, 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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

To a reaction of 1/7-1, 2, 4-triazole-3 -carboxylic acid (226 mg, 2.0 mmol) and (R)- l-(4-methoxyphenyl)ethan-l -amine (0.28 mL, 2.1 mmol) in dry DMF (10 mL) was added l-hydroxybenzotriazole monohydrate (337 mg, 2.2 mmol) and EDC (N-(3- Dimethylaminopropyl)-N’-ethylcarbodiimide) (422 mg, 2.2 mmol) followed by N- methylmorpholine (0.88 mL, 8.0 mmol via syringe). The mixture was stirred at room temperature under nitrogen and the solids were gradually dissolved. The contents were stirred at room temperature for 24 h, and then slowly diluted into iced water and extracted with DCM (50 mL x 2). The DCM phase was washed with ice cold water (100 mL x 2). The DCM phase was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure and chromatographed on silica gel using MeOH and DCM (5:95) as eluents to get the desired amide 22 (287.1 mg, 58 % yield) as a white solid compound. -NMR (400 MHz, DMSO-de): <514.98-14.44 (m, 1H), 9.16-8.08 (m, 2H), 7.34 (d, J= 8.4 Hz, 2H), 6.88 (d, J= 8.8 Hz, 2H,), 5.18-5.04 (m, 1H), 3.73 (s, 3H), 1.48 (d, J= 7.2 Hz, 3H,) ppm. MH+ = 247.1 m/z. 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, 1,2,4-Triazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see. Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; NATIONAL JEWISH HEALTH; WEMPE, Michael Fitzpatrick; VAZQUEZ-TORRES, Andres; DAI, Shaodong; (72 pag.)WO2020/41556; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4928-88-5, 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 4928-88-5 as follows.

Example 5; Scheme 7; Benzoic acid 2-acetoxy-5-(diethoxy- 1-[3-Benzoyloxy-5-(diethoxy-phospriorylmethoxy)- phosphorylmethoxy)-tetrahydro-furan-3-yl ester tpsitrahydro-furan-2-yl]-” * * 1H-[1,2,4]triazole-3-carboxylic acid methyl ester261 5 l-[3-Benzoyloxy-5-(diethoxy-phosphorylmethoxy)-tetrahydro-ftiotaran-2-yl]- UEf-[l,2,4]triazole-3-carboxylic acid methyl ester.; Benzoic acid 2-acetoxy-5-(diethoxy-phosphorylmethoxy)-tetrahydro-furcin-3-yl ester (170 mg, 0.4 mmol), lH-tlA^Triazole-S-carboxylic acid methyl ester (5110 mg, 0.4 mmol) and Bis-(p-nitrophenyl)rhohosphate were reacted according to literature procedure (J. Med. Chem. 2000, 43, 1019-1028). The desired product was isolated in 65percent yield (150 mg). 1H NMR (CDCIa, 300 MHz) delta 8.60 (s, IH), 8.00 (d, 2H, / = 7.8 Hz), 7.60 (t, IH, /= 7.2 Hz), 7.45 (app t, 2H, / = 7.7 Hz), 6.29 (d, IH, /= 1.5 Hz), 5.91-5.98 (m, IH), 5.67-5.71 (m, IH), 4.11-4.23 (m, 4H), 3.96-4.0415 (m, 4H), 3.85-3.92 (m, IH), 2.55-2.72 (m, 2H), 1.29-1.37 (m, 6H). 31P NMR (121.4 MHz, CDCl3) delta 19.8. LRMS (ESI) MH+ C20H27N3O9P requires 484.1 Found 483.8.

According to the analysis of related databases, 4928-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.,; WO2008/5542; (2008); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

626248-56-4, name is 3-(2H-1,2,3-Triazol-2-yl)aniline, 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. Product Details of 626248-56-4

Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (5.00 g, 21.5 mmol) was dissolved in 50 mL DMF. To it were added 3-(2H-l,2,3-triazol-2-yl)aniline (4.13 g, 25.8 mmol) and DIEA (7.50 mL, 43.0 mmol). The mixture was stirred at 40C for overnight. To it was poured 300 mL water. Solid ethyl 4-(3-(2H-l,2,3-triazol-2-yl)phenylamino)-2- (methylthio)pyrimidine-5-carboxylate crashed out. It was collected by filtration, washed with water. The solid was then dissolved in 100 mL dioxane. To it was added LiOH hydrate (2.80 g, 64.5 mmol) and 50 mL water. The mixture was stirred for overnight. To the mixture was added HCl to adjust the pH to 2. Solid carboxylic acid crashed out. It was isolated by filtration, washed with water and dried in vacuum oven. This solid was dissolved in 100 mL DMF. To it were added EDC.HC1 (5.76 g, 30 mmol) and HOBt.H20 (4.60 g, 30 mmol). The mixture was stirred for 2.5 h. To it was added ammonium hydroxide solution (28%, 9.1 mL, 100 mmol). The mixture was stirred for 2 h. To it was poured 300 mL water. Solid 4-(3-(2H- 1,2,3 -triazol-2- yl)phenylamino)-2-(methylthio)pyrimidine-5-carboxamide crashed out. It was collected by filtration, washed with water and dried in vacuum oven (5.77 g). 4-(3-(2H-l ,2,3-Triazol-2-yl)phenylamino)-2-(methylthio)pyrimidine-5-carboxamide (50 mg, 0.15 mmol) was dissolved in 3 mL NMP. To it was added MCPBA (65%, 48 mg, 0.18 mmol). The mixture was stirred for 1.5 h. To it were added DIEA (78 , 0.45 mmol) and tert-butyl (lR,2S)-2-aminocyclohexylcarbamate (64 mg, 0.30 mmol). The mixture was stirred at 90C for 2 h. It was diluted with 100 mL EtOAc, washed with IN NaOH and brine, dried, concentrated in vacuo. The residue was treated with neat TFA at RT for 2 h. It was concentrated and subjected to reverse phase preaparative HPLC to isolate the title compound. MS found for C19H23N90 as (M+H)+ 394.4. UV: lambda=249 nm.

The synthetic route of 626248-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong J.; KANE, Brian; XU, Qing; BAUER, Shawn M.; SONG, Yonghong; PANDEY, Anjali; DICK, Ryan; WO2013/78468; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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. Quality Control of 1-Methyl-1H-1,2,3-triazole

Example 25a: (4-chloro-2-ethyl-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol A solution of -butyllithium in hexanes (2.5 M, 0.17 mL, 0.43 mmol) was added dropwise to a stirring solution of 5 -methyl – 1 H- 1 ,2,3-triazole (38,3 mg, 0.461 mmol, prepared according to PCT Int. Appl., 2008098104) in tetrahydrofuran (1.5 mL) at -50 C. After 20 minutes at -50 C, a solution of (4-chloro-2-ethyl-3-(4-(trif]uoromethyl)benzyl)quinolin-6-yl)(imidazol-5-yl)methanone (0, 145 g, 0.307 mmol, Intermediate 25: step b) in tetrahydrofuran (1 .5 mL) was added dropwise. After 5 minutes at -50 C, the flask was allowed to warm to 0 C. After 30 minutes, the mixture was partitioned between half-saturated aqueous sodium chloride solution (25 mL) and ethyl acetate (50 mL). The layers were separated and the organic layer was dried with sodium sulfate. The dried solution was filtered. Silica gel (3 g) was added to the filtrate and the mixture was concentrated by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a silica gel column for flash column chromatography purification. Elution with dichloromethane initially, grading to 10% methanol-dichloromethane provided the title compound as an off-white solid. The solid was further purified by chiral SFC (Chiralpak AD-H, 5 urn, 250 x 20 mm, mobile phase: 75% CO?, 25% ethanol containing 0.03% isopropylamine) to provide two enantiomers. The first eluting enantiomer was Example 25b: NMR (600 MHz, CDC13) delta ppm 8.30 (d, J ~ 2.1 Hz, IH), 8.02 (d, J = 8.8 Hz, IH), 7.57 – 7.49 (m, 3H), 7.21 (d, ./ 7.9 Hz, 21 1 ;¡¤. 7.17 (s, IH), 6.18 (s, IH), 4.91 (s, IH), 4.49 (s, 2H), 3.95 (s, 31 1). 3.40 (s, 3H), 3.00 – 2.90 (m, 2H), 2.30 (s, 3H), 1.35 – 1.28 (m, 31 1): MS (ESI): mass calcd. for C28H26CIF3 6O, 554.2; m z found, 555,2 [M+H]+. and the second eluting enantiomer was Example 25c: H NMR (600 MHz, CDC13) delta ppm 8.32 (d, J = 2.1 Hz, IH), 7.99 (d, J = 8.8 Hz, IH), 7.56 – 7.51 (m, 3H), 7.21 (d, J = 7.9 Hz, 2H), 7.12 (s. IH), 6.14 (s, i l l). 5.83 (s, i l l). 4.48 (s, 2H), 3.93 (s, 3H), 3.38 (s, 3H), 2.98 – 2.90 (m, 2H), 2.24 (s, 3H), 1 ,34 – 1.27 (m, 3H): MS (ESI): mass calcd. for C28C1F3N6Q, 554.2; m/z found, 555.0 [M+Hf.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-65-5, its application will become more common.

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