Triazoles

Electric Literature of 88671-89-0, 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 88671-89-0 as follows.

EXAMPLE B-2 (Procedure B) 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanamide To a 500 mL flask was charged 75.0 g (0.24 mole) of alpha-n-butyl-alpha(4-chlorophenyl)-1H-1,2,4-triazole-1-propanenitrile followed by 300 mL of 95% sulfuric acid. The mixture was stirred at 90 C. for 7 days after which the mixture was cooled to room temperature, diluted with ice and neutralized with ammonium hydroxide until basic (pH 8). The product was extracted with ethylene dichloride then washed with water and dried over magnesium sulfate. The solvent was concentrated and gave 45 g (56.5% yield) of a solid melting point 197-199 C.

According to the analysis of related databases, 88671-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rohm and Haas Company; US5358939; (1994); A;,
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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

To a mixture of l-fluoro-2-nitrobenzene (1 mL, 12.8 mmol, 1.0 equiv.) and 3-methyl- lH-l,2,4-triazole (1.27 g, 15.3 mmol, 1.2 equiv.) in acetonitrile (20 mL) was added potassium carbonate (5.29 g, 38.3 mmol, 3.0 equiv.) and the mixture was stirred at 60C for 12 hours. The mixture was cooled to 20C, diluted with ethyl acetate (20 mL) and filtered. The filtrate was concentrated under reduced pressure to give a residue which was purified by silica gel chromatography (petroleum ether: ethyl acetate 2: 1 to 1 : 1) to give the desired product as a light yellow solid (1.20 g, 46%); 1H NMR (DMSO-d6, 400 MHz) delta 8.96 (s, 1H), 8.12 (d, 71H), 7.90 – 7.88 (m, 1H), 7.86 – 7.84 (m, 1H), 7.60 (t, 7 = 8.0 Hz, 1H), 2.31 (s, 3H).

The synthetic route of 7170-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIRE HUMAN GENETIC THERAPIES, INC.; MILLER, Thomas; PAPAIOANNOU, Nikolaos; (243 pag.)WO2018/144620; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1157938-97-0, name is 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, 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 1157938-97-0, name: 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

a) Preparation of a Stock-solution of lithium-diisopropylamide (LDA) in tetrahydrofuran (THF): Diisopropylamine (716 mg, 7,1 mmol, 1.05 eq) was dissolved in anhydrous THF (21.3 mL) and the resulting solution was cooled to -78 C under a nitrogen atmosphere. Subsequently, -BuLi (2,7 M solution in w-heptane, 2.5 mL, 6.7 mmol, 1,0 eq) was added in a drop wise fashion over 15 minutes and the reaction mixture was stirred at -78 C for an additional 15 minutes. Then the solution was warmed to 0 C and stirred for 30 minutes after which the stock solution was cooled to -78 C again, b) Coupling reaction: The thus obtained LDA-solution (3,66 mL, 0.98 mmol, 1.1 eq) was transferred to a Schlenk vessel and ethylpropionate (100 mg, 0.98 mmol, 1.1 eq.) was added in a drop wise fashion at -78 C under a nitrogen atmosphere. The resulting mixture was stirred at -78 C for 30 minutes and then l-(2,5-difluorophenyl)-2-(lH-l,2,4-triazol-l-yl)ethanone (200 mg, 0.90 mmol, 1.0 eq.) in THF (3.66 mL) was added in a drop wise fashion over 15 minutes. The reaction mixture was stirred for 2 hours at -78 C and then quenched with acetic acid and warmed to room temperature. The mixture was diluted with aqueous saturated NH4C1 and ethylacetate. The aqueous layer was extracted with ethylacetate (2x) and the combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated in vacuo to give a yellow oil containing the racemic ester I with a diastereomeric excess of 29% in favour of the desired RR/SS diastereomer. Further purification by column chromatography (-heptane/EtOAc/MeOH 60/40/5 v/v/v) provided the RR/SS diastereomer (light yellow solid) as well as the RS/SR diastereomer (off-white solid) in a combined overall yield of 179 mg (0.55 mmol, 61%).

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; BASILEA PHARMACEUTICA AG; VAN SUMMEREN, Ruben; VAESSEN, Harrie; MINK, Daniel; WASER, Mario; WO2014/23623; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 41253-21-8, 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 41253-21-8 as follows.

Intermediate 38: 4-Cyclohexyl-4- [ (1, 2, 4-triazol-1-yl) methyl] piperidine Step A: 1-BOC-4-Cyclohexyl-4- [ (1, 2, 4-triazol-1-yl) methyl] piperidine To a solution of 1-BOC-4-cyclohexyl-4- [ (methanesulfonyloxy) methyl] piperidine (375 mg, 1 mmol) in DMF (10 mL) was added Na-1, 2,4-triazole (273 mg, 3 mmol), and the solution was stirred at 90-100C for 12 h. After DMF was distilled off in vacuo, the reaction mixture was quenched wirh a saturated aqueous NH4C1 solution, and the organic material was extracted with EtOAc. The extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by column chromatography (eluent : acetone/DCM = 3/1) to give the title compound (313 mg, 90%). MS [M+H] = 349 (M+1)

According to the analysis of related databases, 41253-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG LIFE SCIENCES LTD.; YAMANOUCHI PHARMACEUTICAL CO., LTD.; WO2005/47253; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 129027-65-2, 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. 129027-65-2, name is 1-(tert-Butyl)-1H-1,2,3-triazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

To a 250-mL round bottom flask was added a solution of 1-tert-butyl-1H-1,2,3-triazole-4-carbaldehyde (2.47 g, 16.1 mmol, 2.2 eq) in dichloroethane, followed by addition of propargyl amine (361 mg, 72 mmol, 1.0 eq). To this mixture sodium triacetoxyborohydride (3.8 g, 17.9 mmol, 2.5 eq) was added in one portion with vigorous stirring. The reaction mixture was stirred at room temperature for 40 h. 1N H2SO4 (86 mL) was added to the reaction, and the mixture was stirred for 15 min. The pH was adjusted to >10 by addition of potassium carbonate. The reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (3¡Á300 mL). The organic layers were combined, dried over anhydrous MgSO4, and filtered. Solvent was removed and the residue was purified on column to afford the product as a white powder. 1H NMR complies with the reported value.

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

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCACATION; Zeng, Dexing; (26 pag.)US2017/297008; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 20725-34-2, name is 1-(4-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-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 20725-34-2, Product Details of 20725-34-2

In a 20 mL reaction vial, l-(4-bromo-phenyl)-5-methyl-lH-[l ,2,3]triazole-4-carboxylic acid (0.67 g, 2.38 mmol), (R)-l-phenylethanol (0.29 g, 0.29 mL, 2.4 mmol) and triethylamine (0.24 g, 0.33 mL, 2.4 mmol) were combined with toluene (100 mL) to give a yellow solution and to this was added diphenylphosphorylazide (0.65 g, 0.5 mL, 2.4 mmol). The vial’s atmosphere was purged with nitrogren, sealed, heated in a dry block at 80 C for 4 h, and cooled to room temperature overnight. The reaction was diluted with EtOAc (100 mL) and washed with water (100 mL) and brine (50 mL). The aqueous layers were extracted with EtOAc (100 mL). The organic layers were combined, dried over MgS04, filtered, concentrated, dissolved in minimal DCM, and purified by flash chromatography (silica gel, 0% to 25% EtOAc in hexanes). Appropriate fractions combined, concentrated, dried from DCM / hexanes, to give [l-(4-bromo-phenyl)-5-methyl-lH-[l ,2,3]triazol-4-yl]-carbamic acid (R)-l-phenyl-ethyl ester (0.507 g, 53.2% yield) as an off-white solid. LC/MS calcd. for Ci8Hi7BrN402 (m/e) 400/402, obsd. 401/403 (M+H, ES+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GABRIEL, Stephen Deems; HAMILTON, Matthew Michael; QIAN, Yimin; SIDDURI, Achyutharao; WO2013/189865; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 7343-33-1, These common heterocyclic compound, 7343-33-1, name is 5-Bromo-1H-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.

3-bromo-1H-1,2,4-triazole (32.1 mg, 0.217 mmol) and BF3OEt2 (54 mul, 0.426 mmol) were added to a stirred solution of Intermediate 6 (26.0 mg, 0.043 mmol) in 1,2- dichloroethane (0.43 ml). The reaction mixture was a light yellow solution that was heated to 50¡ãC. After 1.75 hr, LCMS and 1H NMR showed complete consumption of Intermediate 6. The reaction mixture was cooled to room temperature, the solvent was evaporated, and the resulting residue was placed under high vacuum. The residue was dissolved in methanol and separated using a single HPLC run on a 19 x 150 mm Sunfire Prep C18 OBD 10 mum column by eluting with acetonitrile/water + 0.1percent TFA. The HPLC fractions containing the fastest eluting regioisomer were combined, the solvent was evaporated under reduced pressure, and the residue was lyophilized from ethanol and benzene to give EXAMPLE 6A (3.6 mg) as a white solid. The HPLC fractions containing the second eluting regioisomer were combined, the solvent was evaporated under reduced pressure, and the residue was lyophilized from ethanol and benzene to give EXAMPLE 6B (13.1 mg) as a white solid. The HPLC fractions containing the slowest eluting regioisomer were combined, the solvent was evaporated under reduced pressure, and the residue was lyophilized from ethanol and benzene to give EXAMPLE 6C (5.8 mg) as a white solid.EXAMPLE 6A:1H NMR (CD3OD, 600 MHz, ppm) delta 0.76 (s, 3H, Me), 0.76 (d, 3H, Me), 0.81 (d, 3H, Me), 0.84 (d, 3H, Me), 0.85 (d, 3H, Me), 0.88 (s, 3H, Me), 0.89 (d, 3H, Me), 0.94 (s, 3H, Me), 1.16 (s, 3H, Me), 1.20 (s, 3H, Me), 1.22-1.35 (m), 1.40-1.44 (m), 1.46-1.65 (m), 1.73-1.96 (m), 2.11-2.22 (m), 2.43 (broad dd, 1H, H13), 2.79 (broad d, 1H), 2.84 (s, 1H, H7), 3.49 (d, 1H), 3.53 (d, 2H), 3.60 (d, 1H), 3.73 (broad d, 1H), 3.94 (d, 1H), 5.50 (dd, 1H, H5), 5.72-5.80 (broad m, 1H, H14), 9.29 (broad s, 1H, triazole). Mass Spectrum: (ESI) m/z = 717.32 (719.32) (M+H).EXAMPLE 6B:1H NMR (CD3OD, 600 MHz, ppm) delta 0.75 (s, 3H, Me), 0.76 (d, 3H, Me), 0.79 (d, 3H, Me), 0.83 (d, 3H, Me), 0.84 (d, 3H, Me), 0.88 (s, 3H, Me), 0.89 (d, 3H, Me), 0.91 (s, 3H, Me), 1.13 (s, 3H, Me), 1.19 (s, 3H, Me), 1.22-1.34 (m), 1.39-1.43 (m), 1.46-1.56 (m), 1.58-1.64 (m), 1.72-1.95 (m), 2.09-2.21 (m), 2.30 (dd, 1H, H13), 2.83 (s, 1H, H7), 2.85 (d, 1H), 3.48 (d, 1H), 3.48 (d, 1H), 3.54 (dd, 1H), 3.60 (d, 1H), 3.88 (d, 1H), 3.95 (d, 1H), 5.47 (dd, 1H, H5), 5.71-5.77 (m, 1H, H14), 8.10 (s, 1H, triazole).Mass Spectrum: (ESI) m/z = 717.32 (719.32) (M+H).EXAMPLE 6C:1H NMR (CD3OD, 600 MHz, ppm) delta 0.76 (s, 3H, Me), 0.77 (d, 3H, Me), 0.82 (d, 3H, Me), 0.85 (d, 3H, Me), 0.86 (s, 3H, Me), 0.86 (d, 3H, Me), 0.89 (d, 3H, Me), 0.92 (s, 3H, Me), 1.16 (s, 3H, Me), 1.20 (s, 3H, Me), 1.22-1.34 (m), 1.39-1.44 (m), 1.48-1.65 (m), 1.76-1.96 (m), 2.11-2.22 (m), 2.41 (dd, 1H, H13), 2.72 (d, 1H), 2.84 (s, 1H, H7), 3.47 (d, 1H), 3.50 (d, 1H), 3.52 (dd, 1H), 3.58 (d, 1H), 3.72 (d, 1H), 3.91 (d, 1H), 5.48 (dd, 1H, H5), 5.51-5.57 (m, 1H, H 14), 8.52 (s, 1H, triazole).Mass Spectrum: (ESI) m/z = 717.32 (719.32) (M+H).

Statistics shows that 5-Bromo-1H-1,2,4-triazole is playing an increasingly important role. we look forward to future research findings about 7343-33-1.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SCYNEXIS, INC.; GREENLEE, Mark, L.; WILKENING, Robert; APGAR, James; SPERBECK, Donald; WILDONGER, Kenneth, James; MENG, Dongfang; PARKER, Dann, L.; PACOFSKY, Gregory, James; HEASLEY, Brian, Haid; MAMAI, Ahmed; NELSON, Kingsley; WO2010/19204; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 7343-34-2, name is 3,5-Dimethyl-4H-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. Quality Control of 3,5-Dimethyl-4H-1,2,4-triazole

To a stirred solution of Compound 1g in ACN (100 ml) were added Cs2CO3 (125.6 g, 386.15 mmol) and ethyl 2-bromopropanoate (39.43 ml, 283.15 mmol) at 25¡ã C. The mixture was stirred for 16 h at room temperature, The progress of the reaction was monitored by TLC (5percent MeOH in DCM, Rf=0.5, PMA active). After completion of the reaction, the reaction mixture was filtered and washed with EtOAc (300 ml). The filtrate was washed with water (2¡Á200 ml), brine (2¡Á200 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain 35 g crude product. The crude product was purified by normal phase column chromatography using silica (100-200 mesh), eluting with 2percent MeOH in DCM. The collected fractions were evaporated to obtain Compound 2g (30 g, 59.17percent) as a pale yellow liquid. The desired isomer was confirmed by NOE analysis. 1H NMR (400 MHz, DMSO-d6) delta ppm: 5.22-5.34 (m, 1H), 4.03-4.18 (m, 2H), 2.32 (s, 3H), 2.16 (s, 3H), 1.60 (d, J=7.23 Hz, 3H), 1.06-1.19 (m, 3H); LCMS: 75.07percent (198.17, M+H), RT=1.18 min.

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

Reference:
Patent; pH Pharma Co., Ltd.; Jammalamadaka, Vasu; Tipton, Kimberly Ann; Satyal, Sanjeev; Huh, Hoyoung; (69 pag.)US2019/84996; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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 6523-49-5, SDS of cas: 6523-49-5

A solution of 2-amino-5-tert-butylbenzoic acid (commercial sources, 500 mg) and formamidine acetate (404 mg) in EtOH (5 ml) was refluxed for 18 h. The cooled mixture was filtered and the precipitate washed with ice-cold EtOH and dried to give the hydroxy quinazoline (394 mg) which was added to thionyl chloride (10 ml) andDMF (cat.) and heated to reflux overnight. The cooled mixture was diluted with EtOAc and poured onto sat sodium bicarbonate (aq). The organic phase was separated, dried and concentrated to a brown solid (327 mg), of which a portion (105 mg) was treated immediately with 4-triazolylaniline (125 mg) in MeCN (4 ml) at reflux overnight. The cooled mixture was partitioned between DCM and sodium bicarbonate and the organic phase concentrated. Purification by chromatography with DCM:EtOH:NH3 (200:8:1) as eluant gave the desired compound. 1H NMR delta 10.16 (IH, s), 9.48 (IH, s), 8.77 (IH, s), 8.62(1H, s), 8.41 (IH, d),8.2 (4H, m), 7.95 (IH, d), 1.64 (9H, s); LC-MS rt 2.18 m/z 343 ES-.

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

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

Adding a certain compound to certain chemical reactions, such as: 10570-40-8, name is 4-Methyl-4H-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 10570-40-8, COA of Formula: C3H5N3

A solution of 4-methyl-1,2,4-triazole (0.32 g, 3.9 mmol) and benzyl bromide (0.50 mL, 1.1 equiv.) in CH3CN (5 mL) was refluxed for 21 h. On cooling, the product crystallized and was collected by filtration and dried. Yield: 0:72 g (74%). M. p. 158 C. – 1H NMR (300 MHz, [D6]DMSO): delta = 3:91 (s, 3H), 5.66 (s, 2H), 7.38 – 7.43 (m, 5H), 9.21 (s, 1H), 10.32 (s, 1H) ppm. – 13C NMR (75 MHz, [D6]DMSO): delta = 34:2, 54.5, 128.8 (5C), 133.4, 143.2, 145:8 ppm. – IR (neat): nu = 2988 w, 2940 w, 1582 m, 1457 w, 1357 w, 1152 m, 999 w, 912 w, 721 s, 695 s, 640 m, 621 m, 614 m cm-1.

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

Reference:
Article; Laus, Gerhard; Kahlenberg, Volker; Wurst, Klaus; Schottenberger, Herwig; Zeitschrift fur Naturforschung – Section B Journal of Chemical Sciences; vol. 69; 9-10; (2014); p. 950 – 964;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics