Triazoles

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, Safety of 1H-[1,2,3]Triazole-4-carboxylic acid

Example 20 3-{(R)-3-(5?-Chloro-2?-fluorobiphenyl-4-yl)-2-[(3H-[1,2,3]triazole-4-carbonyl)amino]propyl}tetrahydrofuran-3-carboxylic Acid (isomers a and b) [0453] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]tetrahydrofuran-3-carboxylic acid (isomer a; 10 mg, 24 mumol, 1.0 eq.) and DIPEA (20 muL, 100 mumol, 4.0 eq.) were dissolved in DMF (100 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 88 mumol, 3.7 eq.), HATU (15 mg, 39 mumol, 1.6 eq.), and DIPEA (40 muL, 200 mumol, 8.0 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for ten minutes, then both solutions were combined and stirred at room temperature and when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture; the organics were then separated, concentrated and purified by preparative HPLC to yield the title compound (isomer a; 7.8 mg). LCMS (ESI): calc. C23H22ClFN4O4=472; obs. M+H=473.0. Retention time: 4.73 min. [0455] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]tetrahydrofuran-3-carboxylic acid (isomer b; 10 mg, 24 mumol, 1.0 eq.) and DIPEA (20 muL, 100 mumol, 4.0 eq.) were dissolved in DMF (100 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 88 mumol, 3.7 eq.), HATU (15 mg, 39 mumol, 1.6 eq.), and DIPEA (40 muL, 200 mumol, 8.0 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for ten minutes, then both solutions were combined and stirred at room temperature. When the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture; the organics were then separated, concentrated and purified by preparative HPLC to yield the title compound (isomer b; 2.9 mg). LCMS (ESI): calc. C23H22ClFN4O4=472; obs. M+H=472.9. Retention time: 4.77 min. [0456] LC/MS Method: flow rate: 1.5 mL/min; Buffer A: 0.1% TFA/H2O; Buffer B 0.1% TFA/MeCN; gradient elution from 5-100% B over 9.6 min, then 100% B for 1.0 minute, detection at 254 nm.

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 BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/209352; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 28938-17-2, name is 4,5-Dibromo-2-methyl-2H-1,2,3-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. HPLC of Formula: C3H3Br2N3

Intermediate 14d (0551) 5-Bromo-2-methyl-2H- 1 ,2,3-triazole-4-carboxylic acid (0552) A solution of 4,5-dibromo-2-methyl-2H-l,2,3-triazole (Intermediate 14e; 144 g, 597.81 mmol) in anhydrous THF (1.5 L) was cooled to -30 C under nitrogen atmosphere and i- PrMgCl (330 mL, 658 mmol, 2M in THF) was added dropwise. The solution was stirred at -30 C for 1 hour, and then bubbled with C02 for 3 hours at <10 C. The reaction was then stirred at 25 C for 16 hours. The mixture was quenched with aqueous HC1 (-3000 mL, 0.1M) to pH = ~2 and extracted with EtOAc (3 L x 3). The organic phase was then extracted with aqueous NaOH (0.1M, 2 L x 3). The aqueous phase was then added to aqueous HC1 (~6 L, 0.1M) to pH=~2 and extracted with EtOAc (3L x 3). The organic phase was dried with Na2S04 and concentrated under vacuum to give 5-bromo-2-methyl- 2H-l,2,3-triazole-4-carboxylic acid (Intermediate 14d; 105 g, 85.26% yield) as a white solid. lH NMR (DMSO, 400 MHz) delta 4.23 (s, 3H). 13C-NMR (400MHz, DMSO) delta 160.86, 138.23, 124.52, 43.38. The synthetic route of 4,5-Dibromo-2-methyl-2H-1,2,3-triazole has been constantly updated, and we look forward to future research findings. Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; FERON, James, Lyman; (80 pag.)WO2017/80980; (2017); 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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C2H5N5

EXAMPLE 31 3,5-Diamino-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole The synthesis method of Example 1-(3) was applied. 3,5-Diamino-1H-1,2,4-triazole (11.0 g), dimethylformamide (100 ml) and methyl isothiocyanate (10.0 g) were used as reagents. After the reaction, recrystallization from ethyl acetate gave 13.0 g of white powdery crystals (yield (68percent). Melting point: 176°-178° C. IR (KBr): 3430, 3280, 1620, 1520 cm-1 1 H-NMR (DMSO-d6) delta: 2.98 (3H, d, J=4.4 Hz), 5.63 (2H, brs), 8.14 (2H, brs),9.19 (1H, m)

The synthetic route of 1455-77-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Green Cross Corporation; US5750545; (1998); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, molecular formula is C3H4N4O2, 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. SDS of cas: 3641-13-2

General procedure: A mixture of benzil (0.01 mol), aldehydes (0.01 mol), 3-amino-1,2,4-triazole-5-carboxylic acid (0.01 mol), ammonium acetate (0.01 mol) and ceric ammonium nitrate (15 mol%) as a catalyst were refluxed in ethanol (15 mL) for about 3-4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was cooled to room temperature. The solid formed was filtered and dried. The crude products were recrystallized by ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3641-13-2, its application will become more common.

Reference:
Article; Nikalje, Anna Pratima G.; Ghodke, Mangesh S.; Kalam Khan, Firoz A.; Sangshetti, Jaiprakash N.; Chinese Chemical Letters; vol. 26; 1; (2015); p. 108 – 112;,
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 1455-77-2 as follows. category: Triazoles

1H-1,2,4-Triazole-3,5-diamine (12.4 g, 0.125 mol) was dissolved in AcOH (50 ml), and diethyl 2-(ethoxymethylene)malonate (32.5 g, 0.15 mol) was added. The solution was refluxed overnight, then cooled, filtered, and dried to give Key Intermediate VI (22 g, 79percent) as a white solid.

According to the analysis of related databases, 1455-77-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WOLKERSTORFER, Andrea; Szolar, Oliver; Handler, Norbert; Cusack, Stephen; Sauvaitre, Thibault; Simon, Celine; Morice, Christophe; Giethlen, Bruno; Langer, Thierry; Smith, Mark; So, Sung-Sau; Classen-Houben, Dirk; Buschmann, Helmut; US2013/317021; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 60166-43-0, name is 1,4-Dimethyl-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 60166-43-0, Safety of 1,4-Dimethyl-1H-1,2,3-triazole

1,4-Dimethyl-1H-1,2,3-triazole (27.4 mg, 0.282 mmol), potassium acetate (92 mg,0.939 mmol), PdOAc2 (4.22 mg, 0.019 mmol), (1S,4r)-4-(5-bromo-2-((5)-1-(3,4- difluorophenyl)-5 -oxopyrrolidin-2-yl)- 1H-benzo[d] imidazol- 1 -yl)cyclohexyl acetate (100 mg, 0.188 mmol) and cataCXium A (13.47 mg, 0.038 mmol) were suspended in 2-methylbutan-2-ol (1234 pi, 11.27 mmol) under nitrogen. The reaction mixture was purged with nitrogen for 5 mm and then heated to 100C for 18 h. The reaction was cooled to RT and partitioned between EtOAc (40 mL) and water (30 mL). The organicphase was separated, washed with brine (25 mL) and then dried over MgSO4, filtered and concentrated in vacuo to afford a yellow oil, which was purified by chromatography on silica gel (24 g column, 0-5% MeOHIDCM) to afford (1S,4r)-4-(2-((5)-1-(3,4- difluorophenyl)-5 -oxopyrrolidin-2-yl)-5 -(1 ,4-dimethyl- 1 H- 1,2,3 -triazol-5 -yl)- 1H- benzo[d]imidazol-1-yl)cyclohexyl acetate (38 mg, 36%) as a colourless solid; Rt 1.93mm (method 1), m/z 549; 1H NMR (d6-DMSO) : 8.06 (1H, d, J=8.6 Hz), 7.84 (1H,ddd, J13.3, 7.4, 2.7 Hz), 7.73 (1H, d, J1.6 Hz), 7.38 (1H, dt, J=10.6, 9.2 Hz), 7.24(1H, dd, J=8.5, 1.7 Hz), 7.16 (OH, d, J=9.3 Hz), 6.13 (1H, d, J7.4 Hz), 5.06-4.94 (1H,m), 4.60 (1H, t, J=12.5 Hz), 3.90 (3H, s), 2.81 – 2.53 (3H, m), 2.48 – 2.39 (2H, m), 2.19(3H, s), 2.15 -2.05 (4H, m), 2.04 (3H, s), 1.98 – 1.88 (1H, m), 1.88 – 1.79 (1H, m), 1.79- 1.63 (2H, m).

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

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

4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, 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. SDS of cas: 4923-01-7

General procedure: Method I. A mixture of Py (4.4 ml) and AcOH (3.0 ml) was stirred and treated by the addition of 5-aminoazole1a-h (0.01 mol) and (2E)-(3-morpholin-4-yl)-acrylonitrile (2) (1.38 g, 0.01 mol). The obtained mixture was refluxed at 150C for 5 h. After refluxing, the mixture was cooled. The precipitate that formed was filtered off, washed with a small amount of EtOH, and dried. Method II. A solution (or suspension) of the appropriate aminoazole 1a-h (0.01 mol) in solvent (15 ml) (EtOH in the case of compound 3a, dioxane in the case of compounds 3b-h) was stirred at 50C and treated by adding 3,3-diethoxypropionitrile (4) (1.5 ml, 0.01 mol), then 36% HCl solution (0.86 ml, 0.01 mol). The reaction mixture was refluxed for 2.5-3 h, the suspension (or solution) was cooled to room temperature, and the target product was isolated by the method indicated for each particular compound.

The synthetic route of 4923-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gazizov, Denis A.; Fedotov, Victor V.; Gorbunov, Evgeny B.; Ulomskiy, Evgeny N.; Yeltsov, Oleg S.; Rusinov, Gennady L.; Rusinov, Vladimir L.; Chemistry of Heterocyclic Compounds; vol. 55; 6; (2019); p. 573 – 577; Khim. Geterotsikl. Soedin.; vol. 55; 6; (2019); p. 573 – 577,5;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

[0742] To a solution of Compound 1 (15.9 mg, 30 f.tmol) indioxane (0.3 mL) was added HCI (149 f.LL, 598 fllllOI). Theresulting solution was stirred at room temperature for 2 hours,and then concentrated in vacuo. In a separate flask, a solutionof 3H-[1,2,3]triazole-4-carboxylic acid (4.1 mg, 36 f.tmol)and HATU (14 mg, 36 f.tmol) in DMF (0.3 mL) was stirred atroom temperature for 30 minutes. After this time, a solution ofthe crude amine in DMF (0.3 mL) was added, followed byDIPEA (16 f.LL, 90 f.tmol). The resulting solution was stirredfor 1 hour at room temperature then concentrated in vacuowhen the reaction was deemed complete by LCMS to yieldCompound 2 (16 mg), which was used without further purification.

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

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

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. 13423-60-4, name is 1-Phenyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H7N3

EXAMPLE 109 1-phenyl-4-(prop-1-yl)triazolium bromide 0.300 g (0.002 mol) 1-phenyltriazole 1 and 0.188 ml (0.254 g, 0.002 mol) 1-bromopropane 2 were dissolved in a pressure tube in 5 ml THF. The reaction mixture was stirred for 1 h at 50 C.; however, because no precipitate formed, the temperature was raised first to 80 (2 h) and then to 110 C. After 21 h at 110 C. the reaction mixture was cooled down. A DC check still indicated considerable amounts of the educt 1, so that additional 0.376 ml (0.508 g, 0.004 mol) of the educt 2 was added and stirring was continued for 24 h at 110 C. Subsequently, the reaction mixture was cooled down to room temperature and the same volume petroleum ether was added. The precipitated solid is filtered off, washed with petroleum ether and dried in HV. M 268.16 Yield: 0.0374 g (7%) 1H-NMR DM-102.w (300 MHz/DMSO): (ppm)=0.98 (t, 3H, 9-H); 3.95 (q, 2H, 8-H); 4.31 (t, 2H, 7-H); 7.70 (m, 3H, 5/5’/6H); 7.96 (d, 2H, 4/4′-H); 9.51 (s, 1H, 1-H); 11.00 (s, 1H, 2-H) 13C-NMR DM-102 (74.475 MHz/DMSO):

According to the analysis of related databases, 13423-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TECHNISCHE UNIVERSITAET DRESDEN; US2011/105761; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7411-23-6, The chemical industry reduces the impact on the environment during synthesis 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life.

3,5-dibromo-iH-1,2,4-triazole (48.1 mg, 0.212 mmol) and BF3OEt2 (53 mul, 0.418 mmol) were added to a stirred solution of Intermediate 6 (25.4 mg, 0.042 mmol) in 1,2- dichloroethane (0.42 ml). The reaction mixture was a yellow solution that was heated to 50C. After 1.5 hr, the reaction mixture had become an orange suspension. 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 purified using a single HPLC run on a 19 x 150 mm Sunfire Prep C 18 OBD 10 mum column by eluting with acetonitrile/water + 0.1% TFA. The HPLC fractions of the faster eluting regioisomer were combined, the solvent was evaporated under reduced pressure, and the residue was lyophilized from ethanol and benzene to give EXAMPLE 33 A (2.1 mg) as a white solid. The HPLC fractions of the slower eluting regioisomer were combined, the solvent was evaporated under reduced pressure, and the residue was lyophilized from ethanol and benzene to give EXAMPLE 33B (25.9 mg) as a white solid.EXAMPLE 33A:1H NMR (CD3OD, 600 MHz, ppm) delta 0.76 (s, 3H, Me), 0.76 (d, 3H, Me), 0.82 (d, 3H, Me), 0.84 (d, 3H, Me), 0.85 (d, 3H, Me), 0.89 (d, 3H, Me), 0.90 (s, 3H, Me), 1.03 (s, 3H, Me), 1.16 (s, 3H, Me), 1.20 (s, 3H, Me), 1.22-1.35 (m), 1.40-1.44 (m), 1.46-1.52 (m), 1.55-1.65 (m), 1.75-1.97 (m), 2.12-2.22 (m), 2.25-2.31 (m), 2.38 (dd, 1H, H13), 2.84 (s, 1H, H7), 2.85 (d, 1H), 3.49 (d, 1H), 3.56 (dd, 1H), 3.56 (d, 1H), 3.61 (d, 1H), 3.96 (d, 1H), 4.19 (d, 1H), 5.53 (dd, 1H, H5), 5.92-5.98 (m, 1H, H14).Mass Spectrum: (ESI) m/z = 795.22 (797.22) (M+H).EXAMPLE 33B:1H NMR (CD3OD, 600 MHz, ppm) delta 0.76 (s, 3H, Me), 0.76 (d, 3H, Me), 0.84 (d, 3H, Me), 0.85 (d, 3H, Me), 0.87 (d, 3H, Me), 0.88 (s, 3H, Me), 0.89 (d, 3H, Me), 0.93 (s, 3H, Me), 1.15 (s, 3H, Me), 1.20 (s, 3H, Me), 1.22-1.34 (m), 1.39-1.43 (m), 1.47-1.65 (m), 1.75-1.96 (m), 2.10-2.22 (m), 2.34 (dd, 1H, H13), 2.84 (s, 1H, H7), 2.96 (d, 1H), 3.48 (d, 1H), 3.54 (dd, 1H), 3.54 (d, 1H), 3.58 (d, 1H), 3.84 (d, 1H), 3.93 (d, 1H), 5.49 (dd, 1H, H5), 5.71-5.77 (m, 1H, H14).Mass Spectrum: (ESI) m/z = 795.21 (797.19) (M+H).

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, 3,5-Dibromo-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP &amp; 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