Triazoles

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. 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 252742-72-6

Example 8: Synthesis of I5-Chloromethyl-2,4-dihydro-[1 ,2,4]triazol-3-one-variant:To a solution of 0.6Og (1.48mmol, 1 equivalent) of III in 3.1 mL of DMF were added 226mg (1.64mmol, 1.1 equivalents) of potassium carbonate at ambient temperature. The mixture was stirred at 209C and a solution of 238mg (1.78mmol, 1.2 equivalents) of 5-Chloromethyl-2,4-dihydro-[1 ,2,4]triazol-3-one in 1.5ml_ of DMF was added dropwise within 15min. The reaction was stirred for 15min at 209C before 1 OmL of water were added dropwise while the product started to crystallize. The resulting suspension was stirred for 10min at 259C before it is cooled to 00C and stirred for 1 h. The crystals was collected by filtration and washed with cold water to give 416mg (68percent) of the title compound after drying under reduced pressure (400C, 10mbar) as a white crystalline product.Example 8a: Synthesis of I lambda^I -Amino^-chloro-eth-^-ylideneJ-hydrazinecarboxylic acid methyl ester-variant: To a solution of 500mg (1.14mmol, 1 equivalent) of III in 4.2mL of acetonitrile were added 546muL (3.29mmol, 2.9 equivalents) of lambda/,lambda/-diisopropylethylamine and 244mg (1.48mmol, 1.29 equivalents) of /V- [1 -Amino-2-chloro-eth-(Z)-ylidene]-hydrazinecarboxylic acid methyl ester. The resulting suspension was stirred at ambient temperature for 3h while a clear solution was formed. The reaction mixture was concentrated under reduced pressure (450C, 100mbar) and the residue was dissolved in 1 OmL of dichloromethane and washed with 1 OmL of a 26.5percent aqueous sodium chloride solution. The organic layer was concentrated under reduced pressure (459C, 100mbar). Then 4.2mL of acetonitrile were added to the residue and the mixture was transferred to a reactor where it was stirred for 55h at 1109C and 1.5bar. Then the reaction mixture was concentrated under reduced pressure (450C, 10 mbar) and the residue was dissolved in 5.6mL of methanol. The reaction mixture was heated to reflux and charcoal was added. The reaction mixture was kept at reflux for 30min before it was filtered over a bed of celite and washed with methanol. The filtrate was concentrated under reduced pressure and then suspended in acetonitrile. The resulting crystalline product I was collected by filtration and washed with cold acetonitrile to give 324mg (53percent) of the title compound as a white crystalline product.Example 9: Synthesis of I without isolation of intermediates:A mixture of 33.5g (77mmol, 1 equivalent) of Xl dissolved in 496ml_ of methanol and 6.69g of Pd/C (10percent) was charged with hydrogen and stirred for 2h at ambient temperature. The catalyst was filtered off and washed three times with 5OmL of methanol. The filtrate was concentrated under reduced pressure (450C, 10mbar) to yield in 34g of III as a colourless oil. This oil was dissolved in 278ml_ of acetonitrile and 28g (218mmol, 2.9 equivalents) of lambda/,lambda/-diisopropylethylamine and 16g (97,8mmol, 1.3 equivalents) of /V-[1 – Amino-2-chloro-eth-(Z)-ylidene]-hydrazinecarboxylic acid methyl ester were added. The mixture was stirred at ambient temperature for three hours and then concentrated under reduced pressure. The residue was dissolved in 30OmL of dichloromethane and washed with 30OmL of a 26.5percent aqueous sodium chloride solution. The organic layer was concentrated under reduced pressure (45¡ãC, 10mbar). Then 13OmL acetonitrile were added and the resulting mixture was transferred to a reactor where it was stirred for 45h at 1100C and 1.5 bar. The reaction mixture was then concentrated under reduced pressure (450C, 10mbar) and the residue was dissolved in 371 mL methanol. The reaction mixture was heated to reflux and charcoal was added. The reaction mixture was kept at reflux for 30min before it was filtered over a bed of celite and washed with methanol. The filtrate was concentrated under reduced pressure and then suspended in 278mL of acetonitrile. The resulting crystals were collected by filtration and washed with acetonitrile to give 377g (69percent) of the title compound as a white crystalline product.NMR: 1H-NMR (DMSOd6, 300MHz) delta (ppm) = 1.36 (d, CH3, 3H, J 6.5Hz), 2.39(dt, CH2, 1 H, J 11.7Hz, J 3.1 Hz), 2.75 (d, CH2, 1 H, J 14.2Hz), 2.84 (d, CH2, 1 H, J 11.7Hz), 3.38 (d, CH2, 1 H, J 13.9Hz), 3.49 (d, CH, 1 H, J 2.54), 3.62 (d, CH2, 1 H, J 10.9Hz), 4.12 (t, CH2, 1 H, J 9.9Hz), 4.33 (d, CH, 1 H, J 2.7Hz), 4.94 (q, CH, 1 H, J 6.5Hz), 7.07 (t, CH, 2H, J 8.8Hz), 7.37 (s, CH, 2H), 7.51 (t, CH, 2H, J 6.1 Hz), 7.83 (S, CH, 1 H), 11.29 (bs, NH, 2H). 13C-NMR (DMSOd6, 75.47MHz) delta (ppm) = 24.75, 50.79, 51.88, 59.07, 68.02, 71.87, 95.77, 114.79, 115.07, 121.39, 121.60, 125.22, 126.87, 128.83, 129.88, 130.31 , 130.74, 131.18, 131.37, 131.47, 133.52, 133.56, 144.24, 146.87, 156.72, 160.45, 163.68.

According to the analysis of related databases, 252742-72-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sandoz AG; WO2009/106486; (2009); 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., Safety of 1-Methyl-1H-1,2,3-triazole

Bis(1-Methyl-1H-1,2,3-triazol-5-yl)methanone A solution of 1-methyl-1H-1,2,3-triazole (0.954 g, 11.4 mmol, prepared according to PCT Int. Appl., 2008098104) in THF (22 mL) was stirred at ?-70 C. under argon while n-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 methoxy(methyl)carbamate (0.665 g, 4.99 mmol) in THF (3 mL) was 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 NH4Cl (3 mL) and the aqueous layer was extracted with THF (1*6 mL). The combined organic layers were dried (Na2SO4), 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*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; US2015/105366; (2015); A1;,
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. 288-88-0, name is 1H-1,2,4-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Formula: C2H3N3

Intermediate 71; 1-Ethyl- IH-I, 2,4-triazole; A solution of DBU (220.2 g, 1.736 moles) in THF (200 ml) was added dropwise to a mechanically stirred suspension of 1, 2,4-triazole (100 g, 1.44 moles) and ethyl iodide (318 g, 2.026 moles) in dry THF (1 L) at 0 C, over a period of 3 hrs via addition funnel. The reaction mixture was allowed to warm to RT and stirred for overnight. The reaction mixture was filtered through celite and washed with THF (2x250ml). The combined filtrates were concentrated and the residue was distilled under reduced pressure to give the product as colorless liquid. (55gm) NMR (400 MHz, CDC13, delta): 1.51(t, 3H), 4.21 (q, 4H), 7.92 (s, IH), 8.05 (s, IH).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; PEER MOHAMED, Shahul, Hameed; WATERSON, David; WO2010/67125; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 16681-67-7, These common heterocyclic compound, 16681-67-7, name is 4-Bromo-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.

4H-[l,2,4]triazolo[4,3-a][l,5]benzodiazepine, 5,6-dihydro-(4R)-l,4-dimethyl-8-(2- methyl- 2H-l,2,3-triazole-4-yl)-6-(4-chloro-phenyl) (Compound 48). A mixture of 4-R-4H- [l,2,4]triazolo[4,3-a][l,5]benzodiazepine, 5,6-dihydro-l,4-dimethyl-8-(4,4,5,5- tetramethyl-1.3.2- dioxaborolan-2-yl)-6-(4-chloro-phenyl) (200 mg, 0.44 mmol), 4-bromo-2-methyl-2H-1.2.3- triazole (72 mg, 0.44 mmol), tetrakis(triphenylphosphine)palladium(0) (51 mg) and potassium carbonate (243 mg, 1.76 mmol) in mixed solution of tetrahydrofuran (10 mL) and water (2 mL) was heated at 100C for 30 minutes under microwave (pressure: 17.2 bar, equipment power : 150W). The reaction mixture was diluted with ethyl acetate (50 mL), washed by brine (20 mL x 3), dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel,dichloromethane/methanol = 10:1) to afford 4-R-4H-[ 1,2,4] triazolo[4,3-a][l,5]benzodiazepine, 5,6-dihydro-l,4-dimethyl-8-(2-methyl-2H-l,2,3-triazole-4-yl)-6-(4-chloro-phenyl) as a white solid (80 mg, 44.5 %).

Statistics shows that 4-Bromo-2-methyl-2H-1,2,3-triazole is playing an increasingly important role. we look forward to future research findings about 16681-67-7.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; HEWITT, Michael, C.; TAYLOR, Alexander, M.; HARMANGE, Jean-Christophe; WO2012/151512; (2012); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7343-33-1, name is 5-Bromo-1H-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 7343-33-1, Computed Properties of C2H2BrN3

To a 250 mL reaction flask was added 3-bromo-lH-l,2,4-triazole (5 g, 33.8 mmol), copper(I) iodide (0.644 g, 3.38 mmol) and cesium carbonate (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 ml) and l-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100 ¡ãC for 20 h. The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite. The Celite was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo.Purification via flash chromatography (silica/EtO Ac/Hex) yielded 3-bromo-l-(4- (trifluoromethoxy)phenyl)-lH-l,2,4-triazole as an off white solid (3.78 g, 12.27 mmol,72.6percent): mp 69-70 ¡ãC; ]H NMR (400 MHz, CDC13) delta 8.44 (s, 1H), 7.70 (d, / = 8.9 Hz, 2H), 7.38 (d, J = 8.5 Hz, 2H); 19F NMR (376 MHz, CDC13) delta -58.04; EIMS m/z 307.

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; DOW AGROSCIENCES LLC; CROUSE, Gary D.; DEMETER, David A.; SPARKS, Thomas C.; WANG, Nick X.; DENT, William Hunter; DEAMICIS, Carl; NIYAZ, Noormohamed M.; BAUM, Erich W.; FISCHER, Lindsey Gayle; GIAMPIETRO, Natalie Christine; WO2013/9791; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-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. COA of Formula: C3H3N3O2

General procedure: General Procedure (GP-Al) for carboxamide formation: A mixture of amine I (1 equiv) , desired carboxylic acid (1 equiv) , triethylamine (Et3N) (3 equiv) , and 2- (lfl-benzotriazole-l-yl) -1 , 1 , 3 , 3- tetramethyluronium hexafluoro-phosphate (HBTU) (1.5 equiv) in DMF (0.25 M) was stirred at room temperature until the reaction was complete by TLC or LC-MS. The mixture was diluted with 0 and extracted with EtOAc. The combined organic extracts were washed with H2O , brine, dried over Na2S0< , filtered, and concentrated under reduced pressure. The resulting residue was purified by either normal phase silica gel column chromatography (typical eluents included either a mixture of or hexanes and EtOAc or a mixture of CH2CI2 and a 90:9:1 mixture of CH2CI2/CHjOH/concentrated NH4OH} or C- 18 reversed phase column chromatography (typical eluents included CCN and H20) to afford the desired carboxamide XX. The product structure was verified by 1H NMR and by mass analysis. Example 2: (lH-1, 2, 4-Triazol-3-yl) ( ( 3a, 5R, 6aS) -5- (2- (trifluoromethyl)phenyl>hexahydrocyclopenta fc]pyrrol-2 (IH) -yl) methanone 18) Step A: Following general procedure GP-A1 , (3aR, 5S, 6aS) -5- (2- (trifluoromethyl) henyl) octahydrocyclopenta [c] yrrole hydrochloride and IH-l , 2 , 4-triazole-3-carboxylic acid were converted to (1H-1,2,4- triazol-3-yl) ( (3ai, SR, 6&S) -5- (2- (trifluoromethyl(phenyl) hexahydrocyclopenta[c]pyrrol-2 (IH) -yl)methanone as a white solid (0.071 g, 52%): NMR (500 MHz, CDC13) delta 12.7.1 (bs, IH) , 8.12 (bs, IH) , 7.67 (m, IH), 7.49 (m, 2H) , 7.26 (m, IH) , 4.43 (m, 2H) , 3.93 (m, 2H) , 3.53 (m, IH) , 3.08-2.81 (m, 2H) , 2.42 (m, 2H) , 1.65 (m, 2H) ; ESI MS m/z 351 [M + H]*.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4928-87-4, its application will become more common.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; PETRUKHIN, Konstantin; CIOFFI, Christopher; JOHNSON, Graham; DOBRI, Nicoleta; FREEMAN, Emily; CHEN, Ping; CONLON, Michael; ZHU, Lei; WO2014/152018; (2014); 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. 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole, A new synthetic method of this compound is introduced below., category: Triazoles

To a stirred solution of EE-3 (10 g, 44.08 mmol) in DMF (60 mL) is added K2C03 (9.158 g, 66.12 mmol) at room temperature then the reaction mixture is stirred at room temperature for 1 hour. EE-4 (5.422 g, 44.08 mmol) is added and the reaction mixture is stirred at room temperature for 12 hours. The reaction mixture is quenched with water then extracted with EtOAc twice. The organics are combined and concentrated. The residue is purified by column chromatography on silica gel eluting with EtOAc in heptane to yield Intermediate EE-5.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HUGHES, Robert Owen; LI, Xiang; NEMOTO, Peter Allen; SMITH KEENAN, Lana Louise; WU, Lifen; XIONG, Zhaoming; (65 pag.)WO2018/111803; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 288-88-0, name is 1H-1,2,4-Triazole, molecular formula is C2H3N3, 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: C2H3N3

STR6 A solution of 17.9 g (0.075 mole) of 2-(4-chlorophenylethyl)-2-tert.-butyloxirane and 6.9 g (0.1 mole) of 1,2,4-triazole in 30 ml of ethanol in a sealed tube is heated at 150 C. for 20 hours. The tube is allowed to cool and the reaction solution is evaporated. The residue is dissolved in ether, washed three times with water and once with sodium chloride solution, dried over sodium sulphate and evaporated. The residue is chromatographed over a column of silican gel (mobile phase: dichloroethane/ethyl acetate 1:1). 12.3 g (53.2% of theory) of 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-3-pentanol are obtained as a viscous oil. The hydrochloride of melting point 212 C. is obtained in virtually quantitative yield by customary reaction with ethereal hydrogen chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-88-0, its application will become more common.

Reference:
Patent; Bayer Aktiengesellschaft; US4668660; (1987); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 41253-21-8, 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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

2-(lH-l,2,4-Triazol-l-yl)benzonitrile. A suspension of 2-fluorobenzylnitrile (3.0 g, 25 mmol) and 1,2,4-triazole sodium salt (2.4 g, 27 mmol) were stirred in tetrahydrofuran (7 mL) and dimethylformamide (14 mL) at 95 0C for 18 h. After cooling and concentrating, the product was crystallized from hot CH2Cl2/hexane (1:1) to give the title compound as a white solid (4.25 g, 100% yield). 1H-NMR (300 MHz, CDCl3) 6 ppm: 8.74 (IH, s), 8.16 (IH, s), 7.82 (IH, dd, J= 4.9,1.3 Hz), 7.77-7.25 (2H, m), 7.57-7.51 (IH, m). LCMS [M+H]+ calcd for C9H7N4: 171.06; found: 171.12.

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, Sodium 1,2,4-triazol-1-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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: C2H3N3

2-iodobenzoic acid (1 g, 4.03 mmol), 2H-l,2,3-triazole (0.334 g, 4.84 mmol), copper(I) iodide (0.768 g, 4.03 mmol), cesium carbonate (2.63 g, 8.06 mmol) were reacted in DMF at 120 C under microwave irradiation for 20 minutes. Then the reaction was monitored confirming the presence of the required product. Large amount of starting material resulted left. The reaction was further irradiated for 20 minutes at 120 C. Solvent was then removed under vacuum, poured into water (100 ml) and neutralised with 37% HC1. Aqueous phase was extracted with Et20 (3×100 ml), and the collected organic phases were concentrated to give 1 g of crude material. This was purified with Biotage SP1 (over a 340g C18 column) eluting with a gradient of ACN and water (modified with 0.5% HCOOH). Fractions were collected and concentrated under vacuum to give the title compound D43 as colourless solid (140 mg). UPLC (GEN QC Basic): rt = 0.29 minutes, peak observed: 188 (M-l) C9H7N302 requires: 189. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 6.47 (br. s., 1 H) 7.47 – 7.59 (m, 1 H) 7.66 (t, 1 H) 7.75 – 7.87 (m, 3 H) 7.91 (d, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-36-8, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89606; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics