Triazoles

Related Products of 16681-67-7,Some common heterocyclic compound, 16681-67-7, name is 4-Bromo-2-methyl-2H-1,2,3-triazole, molecular formula is C3H4BrN3, 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 solution of 4-bromo-2-methyl-2H-1,2,3-triazole (250 mg, 1.543 mmol) in 1,4-dioxane (20 mL) were added 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (780.9 mg, 3.086 mmol) and KOAc (454.8 mg, 4.630 mmol). The mixture was degassed for 10 mm, followed by addition of Pd(Ph3P)4 (126.0 mg, 0.154 mmol), and degassed for another 10 mm. The reaction mixture was sealed, stirred at 80C for 3h, and cooled to rt. To the mixture was added a mixture of Intermediate 3 (426.7 mg, 0.77 1 mmol) and K2C03 (1.064 g, 7.7 17 mmol) in toluene/H20/ethanol (30 mL). The mixture was degassed for 10 mm, followed by addition of Pd(Ph3P)4 (178.2 mg, 0.154 mmol), and degassed for anotherlO mm. After being stirred at 80C for 16h, the mixture was cooled to rt, diluted with cold water, and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The crude compound was purified by column chromatography using 60% EtOAc/hexanes to afford 58-1 (300 mg, 35%). LCMS: 556.1 [M+Hjt

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

Reference:
Patent; KALYRA PHARMACEUTICALS, INC.; HUANG, Peter, Qinhua; KAHRAMAN, Mehmet; BUNKER, Kevin, Duane; (194 pag.)WO2018/67512; (2018); 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.

To a solution of tert-butyl-3,8-diazabicyclo[3.2.1 ]octane-3-carboxylate (0.3 mmol, 750 mu, 0.4 M) in DCE were added benzenesulfonyl chloride (0.45 mmol, 900 mu, 0.5M, 1 .5 eq) in DCE and 0.9 mmol DIPEA (156 mu, 3 eq) and the mixture was shaken overnight at RT. 2 mL TFA/DCE 3:1 were added and the mixture was shaken at RT for 3 h. After evaporation of the solvent, 1 H-1 ,2,3-triazole-5-carboxylic acid (0.6 mmol, 1 .2 mL, 2 eq, 0.5M) in NMP, 928 mu DIPEA (3.6 mmol, 12 eq; adjustment of pH to 8) and HATU (0.6 mmol, 1.2 mL, 2 eq, 0.5 M) in NMP were added and the mixture was shaken overnight to yield after preparative HPLC 26 mg (25%) of the title compound 3,8- diazabicyclo[3.2.1 ]oct-3-yl(1 H-1 ,2,3-triazol-4-yl)methanone.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-[1,2,3]Triazole-4-carboxylic acid, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SIEBENEICHER, Holger; STEUBER, Holger; TER LAAK, Antonius; NUBBEMEYER, Reinhard; ROTTMANN, Antje; IRLBACHER, Horst; BADER, Benjamin; PETERS, Michaele; WAGENFELD, Andrea; TEREBESI, Ildiko; (123 pag.)WO2017/202817; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7411-23-6, A common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, 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 solution of 3,5-dibromo-lh-l,2,4-triazole (150.0 g, 661.2 mmol) in tetrahydrofuran (1500 mL) was slowly added p-toluenesulfonic acid (17.1 g, 99.2 mmol), followed by 3,4-dihydro-2h-pyran (166.9 g, 1983.6 mmol) at 0 C. After addition, the reaction mixture was heated at 70 C for 3 h and concentrated under reduced pressure. The residue was poured into water (500 mL) and adjusted to pH = 9 by addition of saturated aqueous sodium bicarbonate. The resulting mixture was extracted with ethyl acetate (3 x 400 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduce pressure. The resulting crude product was washed with methanol (2 x 50 mL), dried under reduced pressure to give crude 3,5-dibromo-l-tetrahydropyran-2-yl-l,2,4- triazole (155 g, 75%) as a white solid. XH NM (400 MHz, CDCI3) delta 5.49 – 5.46 (m, 1H), 4.12 – 3.99 (m, 1H), 3.72 – 3.61 (m, 1H), 2.38 – 2.26 (m, 1H), 2.18 – 2.07 (m, 1H), 1.98 – 1.90 (m, 1H), 1.78 – 1.60 (m, 3H).

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; HAMILTON, Gregory; PATEL, Snahel; ZHAO, Guiling; DANIELS, Blake; STIVALA, Craig; (208 pag.)WO2019/72942; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 61-82-5, These common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, 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 aldehyde (1 mmol), dimedone (1 mmol), 3-amino-1,2,4-triazole (1 mmol), and [C4(H-DABCO)2][HSO4]4 (16 mg) washeated in an oil bath (90 C) under solvent-free conditions. Aftercompletion of the reaction, as identified by TLC, using n-hexane:EtOAc (7:3) as the eluent, 10 mL of water was added and stirredfor 10 min. The catalyst was dissolved in water and the solid wasfiltered off and washed with warm EtOH, to obtain the pure targetmolecule.

Statistics shows that 1H-1,2,4-Triazol-5-amine is playing an increasingly important role. we look forward to future research findings about 61-82-5.

Reference:
Article; Safari, Niloufar; Shirini, Farhad; Tajik, Hassan; Journal of Molecular Structure; vol. 1201; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 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 16681-70-2, Recommanded Product: 16681-70-2

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 2-(2-oxo-pyrrolidin-1-yl)-ethyl ester (52.6 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 (13 mg; purity 95%). MS m/z [M+H]+ calc’d for C28H33N5O5, 520.25. found 520.4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-[1,2,3]Triazole-4-carboxylic acid, and friends who are interested can also refer to it.

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

Synthetic Route of 23579-79-5, These common heterocyclic compound, 23579-79-5, name is 3,5-Dibromo-1-methyl-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.

LiHMDS (1 Min THF, 420 mL, 420 mmol) was added dropwise at 0 C to a cooled (ice bath) solution of 3-amino-4-fluorobenzotrifluoride (70 mL, 527.8 mmol) and 1H-1,2,4-Triazole, 3,5-dibromo-1-methyl-(46a, 50 g, 207.6 mmol) in anhydrous THF (500 mL). The reaction mixture was stirred at room temperature (rt) for 20 h. A saturated aqueous NH4Cl solution was added slowly. The reaction mixture was extracted with dichloromethane (DCM) and the organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The resulting slurry was triturated in heptane/DIPE and a solid was formed,filtered and dried under vacuum at 60 C, to provide 65 in 78% yield; mp 159.2 C. 1H NMR (600 MHz, CDCl3) delta ppm 3.77 (s, 3H), 6.37 (d, J = 3.9 Hz, 1H),7.20-7.24 (m, 1H), 7.27-7.29 (m, 1H), 8.34 (dd, J = 7.7, 2.2 Hz, 1H). MS (ESI) m/z 339 [M+H].+ Anal. (C10H7BrF4N4) C, H, N.

Statistics shows that 3,5-Dibromo-1-methyl-1H-1,2,4-triazole is playing an increasingly important role. we look forward to future research findings about 23579-79-5.

Reference:
Article; Velter, Adriana I.; Bischoff, Franois P.; Berthelot, Didier; De Cleyn, Michel; Oehlrich, Daniel; Jaroskova, Libuse; Macdonald, Gregor; Minne, Garrett; Pieters, Serge; Rombouts, Frederik; Van Brandt, Sven; Van Roosbroeck, Yves; Surkyn, Michel; Trabanco, Andrs A.; Tresadern, Gary; Wu, Tongfei; Borghys, Herman; Mercken, Marc; Masungi, Chantal; Gijsen, Harrie; Bioorganic and Medicinal Chemistry Letters; vol. 24; 24; (2014); p. 5805 – 5813;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, 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. Application In Synthesis of 1,4-Dimethyl-1H-1,2,3-triazole

A vessel containing (S)-6-(5-bromo-1-(trans-4-hydroxycyclohexyl)-1H-benzo[d]imidazol-2-yl)- 1 -(3 ,4-difluorophenyl)piperidin-2-one (intermediate 17, 50 mg,0.10 mmol), 1,4-dimethyl-1H-1,2,3-triazole (15 mg, 0.15 mmol), potassium acetate (50mg, 0.51 mmol) and tert-amyl alcohol (0.75 mL) was evacuated then backfilled withnitrogen three times. cataCXium A Pd G3 (7 mg, 10 tmol) was added and the mixturewas heated to 100 C for 18 h. The mixture was diluted with water (8 mL) then extracted with dichloromethane (3 x 8 mL). The combined organic phases were concentrated under reduced pressure to give the crude product. The crude product was purified by chromatography on silica gel (4 g column, 50-100% MeAc/isohexane) to afford a pale brown gum. The gum was triturated in tert-butyl methyl ether to yield (S)1 -(3 ,4-difluorophenyl)-6-(5-( 1 ,4-dimethyl- 1H- 1,2,3 -triazol-5-yl)- 1 -(trans-4- hydroxycyclohexyl)-1H-benzo[d]imidazol-2-yl)piperidin-2-one (26 mg, 0.047 mmol, 48% yield) as atan solid. LCMS (method 1): Rt 1.50 mi m/z 521 (M+H)t 1HNIVIR(DMSO-d6) 7.91 – 7.77 (m, 2H), 7.44 – 7.36 (m, 1H), 7.36 – 7.29 (m, 1H), 7.23 (dd, J= 8.5, 1.7 Hz, 1H), 7.09 -7.00 (m, 1H), 5.79 (t, J = 4.6 Hz, 1H), 4.71 (d, J = 4.1 Hz,1H), 4.41 – 4.26 (m, 1H), 3.94 (s, 3H), 3.73 – 3.61 (m, 1H), 2.55 (dt, J = 9.8, 6.2 Hz,2H), 2.48 – 2.24 (m, 2H), 2.23 (s, 3H), 2.21 – 2.12 (m, 1H), 2.08 – 1.91 (m, 3H), 1.91 -1.70 (m, 3H), 1.50- 1.35 (m, 2H), 1.25- 1.15 (m, 1H).

The synthetic route of 60166-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELLCENTRIC LTD; PEGG, Neil Anthony; TADDEI, David Michel Adrien; SHANNON, Jonathan; PAOLETTA, Silvia; QIN, Ting; HARBOTTLE, Gareth; (95 pag.)WO2018/73587; (2018); 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Methyl-1H-1,2,4-triazole

CuI (1.71 g, 8.9 mmol) and N,N’-dimethylethylenediamine (1.91 ml, 17.92 mmol) were added to a mixture of 2-amino-5-iodopyridine (5.03 g, 22.4 mmol), 3 -methyl- IH- 1,2,4- triazole (2.42 g, 29.1 mmol) and Cs2CO3 (14.60 g, 44.81 mmol) in DMF (40 ml). The r.m. was heated at 110 0C for 7 h., the r.m. was cooled, EtOAc was added and the mixure was washed with H2O. The H2O layer was extracted 5 times with EtOAc. The combined organic layers were dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was purified by RP preparative HPLC [RP Shandon Hyperprep C18 BDS (8 mum, 250 g, LD. 5 cm); mobile phase: a gradient of (0.25 % NH4HCO3 solution in H2O)/MeOH/CH3CN]. The product fractions were collected and the solvent was evaporated. Yield: 1.5 g of intermediate 56 (38 %). –

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; TRESADERN, Gary, John; TRABANCO-SUAREZ, Andres, Avelino; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2010/70008; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 288-36-8 name is 1H-1,2,3-Triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate 1 : 5-Fluoro-2-[1 ,2,3]triazol-2-yl-benzoic acid.5-Fluoro-2-[1 ,2,3]triazol-2-yl-benzoic acid. To a solution of 5-fluoro-2- iodo-benzoic acid (3.86 g, 14.65 mmol), 2H-[1 ,2,3]triazole (2.5 g, 36.2 mmol), Cs2C03 (8.62 g, 24.5 mmol), frans-N,N’-dimethyl-cyclohexane-1 ,2-diamine (0.4 mL), Cul (244 mg) and DMF (13 mL) were added to a microwave ready vessel and heated to 100 C for 10 min. The mixture was cooled, diluted with water, and extracted with EtOAc. The aqueous layer was acidified and extracted with EtOAc. The organic layer was dried over Na2S04 and concentrated.Chromatography (DCM to 10% MeOH/1 % HOAc/DCM) gave the product as a white powder (2.14 g, 71 %). 1H NMR (400 MHz, CD3OD): 7.91 (s, 2H), 7.76 (dd, J = 8.9, 4.8 Hz, 1 H), 7.59 (dd, J = 8.5, 2.9 Hz, 1 H), 7.49 – 7.42 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-1,2,3-Triazole, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4928-88-5,Some common heterocyclic compound, 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, molecular formula is C4H5N3O2, 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 3A Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate (20) A mixture of methyl 1,2,4-triazole-3-carboxylate (0.64 g, 5 mmol), 1,2,3,5-tetra-O-acetyl-beta-L-ribofuranose (2) (1.5 g, 4.72 mmol) and bis(p-nitrophenyl)-phosphate (20 mg) were placed in a pear shaped flask and placed in a preheated oil bath at (160-165¡ã C.). The flask was connected to a water aspirator and kept at 160-165¡ã C. (oil bath temperature) under reduced pressure with stirring for 25 min. The reaction mixture was removed, cooled and diluted with EtOAc (150 mL) and sat. NaHCO3 (100 mL). The product was extracted in EtOAc. The organic extract was washed with water (100 mL) and brine (50 mL), dried and evaporated to dryness. The residue that obtained was purified by flash column of silica gel using CHCl3 –>EtOAc as the eluent. The pure fractions were collected and evaporated to dryness to give 1.2 g (66percent) of pure product: 1 H NMR (CDCl3) delta 2.10 (3s, 9H, 3 COCH3), 3.98 (s, 3H, OCH3), 4.22 (m, 1H), 4.46 (m, 2H), 5.54 (t, 1H), 5.76 (m, 1H), 6.04 (d, 1H, C1′,), and 8.38 (s, 1H, C3 H). Anal. Calc. for C15 H19 N3 O9 (385.22): C, 46.75; H, 4.97; N,10.91. Found: C, 46.82; H, 4.57; N=10.71.

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

Reference:
Patent; ICN Pharmaceuticals, Inc.; US6130326; (2000); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics