Triazoles

Related Products of 4923-01-7, A common heterocyclic compound, 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, molecular formula is C3H6N4, 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.

General procedure: 3-Amino-1,2,4-triazole 8a-f (1.0 mmol), o-hydroxybenzaldehyde9a-e (1.0 mmol), acetone (10) (0.22 ml,3.0 mmol), and abs. EtOH (2 ml) were mixed in amicrowave process vial, and then 4 N solution of HCl indioxane (0.07 ml, 0.3 mmol) was added. The mixture wasirradiated at 150C for 30 min. The reaction mixture wascooled by an air flow and stirred for 24 h at roomtemperature for complete precipitation of the product. Theprecipitate was filtered off, washed with EtOH (1 ml) andEt2O (3×1 ml), and dried. Compounds 1a-w were obtainedin a form of white solids.

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:
Article; Guemue?, Mustafa K.; Gorobets, Nikolay Yu.; Sedash, Yuriy V.; Chebanov, Valentin A.; Desenko, Sergey M.; Chemistry of Heterocyclic Compounds; vol. 53; 11; (2017); p. 1261 – 1267; Khim. Geterotsikl. Soedin.; vol. 53; 11; (2017); p. 1261 – 1267,7;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 6523-49-5, 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. 6523-49-5 name is 4-(1,2,4-Triazol-1-yl)aniline, 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.

Title Compound 300 mg of the product, 7A, was dissolved in THF and 0.15 g of Intermediate 45B and 0.1 ml of pyridine were added. The mixture was refluxed for 3 hours, then dilute HCl was added. A precipitate was obtained which was filtered and washed with acetone to give 200 mg of an off-white product. Microanalysis: theory(%, 1 H20): C, 50.5; H, 3.00; N, 17.1; obtained (%): C, 50.5; H, 2.80; N, 16.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1,2,4-Triazol-1-yl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Sartori, Eric; Maillet, Magali; Paugam, Marie France; Nicolai, Eric; Lawrence, Michael; US2005/143384; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-65-5, 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

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) (Aldrich) 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), the title compound as blunt needles.

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

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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 1001401-62-2,Some common heterocyclic compound, 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, molecular formula is C9H7N3O2, 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 1 2-(((3R,6R)-l-(2-(2H-l,2,3-Triazol-2-yl)benzoyl)-6-methylpiperidin-3- yl)amino)isonicotinonitrile Step 1: (2R,55′)-Benzyl 2-methyl-5-((methylsulfonyl)oxy)piperidine-l-carboxylate (2) A solution of (2R,55)-benzyl 5-hydroxy-2-methylpiperidine-l-carboxylate (15.0 g, 60.2 mmol), 4-dimethylamino pyridine (0.74 g, 6.0 mmol), and (( (401 mL) was treated with DIEA (15.8 mL, 90.0 mmol) and cooled at 0 C. Methanesulfonyl chloride (5.9 mL, 75 mmol) in (( (67 mL) was added dropwise and stirring continued at 0 C for 2 h. The reaction was diluted with water and 1 N HQ and the separated organics were washed with brine, dried over MgS04, filtered, concentrated and dried, providing the crude title compound which was used without further purification. LRMS m/z (M+H) 328.3 found, 328.1 required. Step 2: (2R,5R)-Benzyl 5-azido-2-methylpiperidine-l-carboxylate (3) A solution of crude (2R,55)-benzyl 2-methyl-5-((methylsulfonyl)oxy)piperidine- 1 -carboxylate (19.7 g, 60.2 mmol) and sodium azide (6.65 g, 102 mmol) in DMF (86 mL) was heated to 85 C overnight. The reaction was diluted with EtOAc, washed 2x with water, lx with brine, dried over magnesium sulfate, filtered, and concentrated, providing the crude title compound which was used without further purification. LRMS m/z (M+H) 275.3 found, 275.2 required. Step 3: (2R,5R)-Benzyl 5-amino-2-methylpiperidine-l -carboxylate (4) To a solution of (2R,5R)-benzyl 5-azido-2-methylpiperidine-l-carboxylate (15.2 g, 55.4 mmol) in THF (111 mL) was added trimethylphosphine (1.0 M in toluene, 55.4 mL, 55.4 mmol) dropwise over 20 min. The reaction was quenched with water (30 mL) and stirred at RT overnight. The mixture was diluted with dichloromethane, washed 2x with water, lx with brine, dried over magnesium sulfate, filtered, and concentrated, providing the crude title compound as an orange oil which was used without further purification. LRMS m/z (M+H) 249.6 found, 249.3 required. Step 4: (2R,5R)-Benzyl-5-((?ert-butoxycarbonyl)amino-2-methylpiperidine-l-carboxylate (5) A solution of (2R,5R)-Benzyl 5-amino-2-methylpiperidine-l-carboxylate (3.08 g, 12.4 mmol) and 4-dimethylaminopyridine (0.015 g, 0.12 mmol) in dichloromethane (62 mL) was treated with a solution of di-tert-butyl dicarbonate (2.91 mL, 12.5 mmol) in dichloromethane (20 mL) dropwise and stirred at RT overnight. The reaction was concentrated in vacuo, providing the crude title compound which was used without further purification. LRMS m/z (M+H) 349.4 found, 349.3 required. Step 5: tert-Butyl ((3R,6R)-6-methylpiperidin-3-yl)carbamate (6) A solution of (2R,5R)-benzyl-5-((/er/-butoxycarbonyl)amino-2-methylpiperidine- 1 -carboxylate (4.32 g, 12.4 mmol) and palladium (10 wt % on activated carbon, 0.300 g, 2.82 mmol) in degassed ethanol (100 mL) and methanol (5 mL) was stirred for 72 h under an atmosphere of hydrogen gas. Additional palladium (10 wt % on activated carbon, 0.10 g, 0.94 mmol) was added, and the reaction was recharged with hydrogen gas and allowed to stir at RT overnight. The degassed mixture was then filtered over celite, washing with EtOH. The filtrate was concentrated to give the titled compound as a crude, light yellow solid which was used without further purification. Step 6: tert-Butyl((3R,6R)-l-(2-(2H-l,2,3-triazol-2-yl)benzoyl)-6-methylpiperidin-3- yl)carbamate (7) A solution of 2-(2H- 1,2,3 -triazol-2-yl)benzoic acid (4.24 g, 22.40 mmol), tert- butyl ((3R,6R)-6-methylpiperidin-3-yl)carbamate (3.20 g, 14.93 mmol), l-hydroxy-7- azabenzotriazole (4.06 g, 29.9 mmol), EDC (5.72 g, 29.9 mmol), and DIEA (15.65 mL, 90 mmol) in DMF (100 mL) was heated at 50 C overnight. The reaction was diluted with saturated, aqu. aHC03 and extracted 2x with EtOAc. The organics were washed with brine, dried over MgS04, filtered, and concentrated. The residue was purified by silica gel gradient chromatography (0-80% EtOAc in hexanes), providing the title compound. LRMS m z (M+H) 386.4 found, 386.2 required. Step 7: (2-(2H-l,2,3-Triazol-2-yl)phenyl)((2R,5R)-5-amino-2-methylpiperidin-l-yl)methanone (8) A solution of tert-butyl((3R,6R)-l-(2-(2H-l,2,3-triazol-2-yl)benzoyl)-6- methylpiperidin-3-yl)carbamate (3.6 g, 9.3 mmol) in EtOAc (78 mL) was saturated with HC1 (g) and stirred for 2 h. The reaction was concentrated and the residue basified with 1 N NaOH. The mixture was extracted 3x with EtOAc, then the organics were washed with brine, dried over MgS04, filtered, and concentrated. The residue was purified by silica gel gradient chromatography (0-20% MeOH in CH2C12), providing the title compound. LRMS m/z (M+H) 286.3 found, 286.3 required. Step 8: 2-(((3R,6R)-l-(2-(2H- 1,2,3 -triazol-2-yl)benzoyl)-6-methylpiperidin-3- yl)amino)isonicotinonitrile A solution of (2-(2H-l,2,3-triazol-2-yl)phenyl)((2R,5R)-5-amino-2- methylpiperidin- 1 -yl)methanone (400 mg, 1.40 mmol) 2-fluoroisonicotinonitrile (342 mg, 2.80 mmol), and cesium carbonate (776 mg, 2.383 mmol) in DMSO (4673 muKappa) was heated at 50 C for 48 h. The reaction was cooled, dilut…

The synthetic route of 1001401-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2014/85208; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature 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 A 2-(2H-l .2.3-Triazol-2-yl)benzoyl acid A solution of 2-iodobenzoic acid (3.0 g, 12.09 mmol) in DMF (1.0 mL) was treated with 1,2,3-triazole (1.5 g, 21.7 mmol), copper(I) iodide (0.25 g, 1.2 mmol), Cs2C03 (7.08 g, 21.7 mmol), and fras-N,N’-dimethylcyclohexane-l ,2-diamine (0.31 g, 2.17 mmol). The mixture was heated at 120 C for 12h. The reaction was cooled to rt, diluted with EtOAc, and filtered through Celite. The residue was purified by gradient elution on Si02 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the title compound.1HNMR (500 MHz, DMSO-d6) delta 13.05 (br s, 1H), 8.12 (s, 2H), 7.81-7.52 (m, 4H) ppm. LRMS m/z (M+H) 190.2 found, 190.2.

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; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (116 pag.)WO2016/100161; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7170-01-6, These common heterocyclic compound, 7170-01-6, name is 3-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.

General procedure: To 3,6-dichloropyridazine (500 mg, 3.36 mmol) in 5 mL DMF are added 1H-1,2,4-triazole (460 mg, 6.71 mmol) and cesium carbonate (2.41 g, 7.38 mmol) and the reaction mixture is stirred at 60 C. for 18 h. The mixture is quenched with water and the precipitation is filtered, washed and dried to give 0.7 g of the product. (0171) C8H6N8 (M=214.19 g/mol) (0172) ESI-MS: 215 [M+H]+ (0173) 1H NMR (400 MHz, DMSO-d6) delta=9.66 (s, 1H), 8.47 (s, 1H), 8.44 (s, 1H)

Statistics shows that 3-Methyl-1H-1,2,4-triazole is playing an increasingly important role. we look forward to future research findings about 7170-01-6.

Reference:
Patent; Boehringer Ingelheim International GmbH; Larsen, Janus Schreiber; Binder, Florian; Cui, Yunhai; Hucke, Oliver; Lipinski, Radoslaw; Montel, Florian; Ostermeier, Markus; Perera, Alexandre; Peters, Stefan; US2020/24261; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 1001401-62-2, 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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

A solution of 2-iodobenzoic acid (3.0 g, 12.09 mmol) in DMF (1.0 mL) was treated with 1,2,3-triazole (1.5 g, 21.7 mmol), CsCO3 (7.08 g, 21.7 mmol), and trans-N,N’- dimethylcyclohexane-l52-diamine (0.31 g, 2.17 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to rt, diluted with EtOAc5 and filtered through Celite. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting desired 2-(2H-l52,3-triazol-2-yl)benzoyl acid. Data for 2-triazolyl isomer: 1HNMR (500 MHz, DMSO-d6) delta 13.05 (br s , IH)5 8.12 (s, 2H), 7.81-7.52 (m, 4H) ppm. The undesired l-(2H-l,2,3-triazol-2-yl)benzoic acid eluted second. A portion of the desired acid (0.10 g, 0.53 mmol) was treated with thionyl chloride (0.59 g, 5.3 mmol) in dichloromethane (5.0 mL) at rt. After stirring at RT for 1 h, the mixture was concentrated, azeotroping with benzene to yield acid chloride A-3.

The synthetic route of 2-(2H-1,2,3-Triazol-2-yl)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2007/126934; (2007); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 4922-98-9, 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. 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of aminotriazole 11a?m (3.1mmol), glacial acetic acid (5mL), and diethyl ethoxymethylenemalonate (4.6mmol) was refluxed for 3h. After cooling to room temperature, the resulting precipitate was collected by filtration, washed with cold water and dried. The residue was stirred with cold ethyl ether (20mL) and filtered to afford the desired product. Following general procedure C, compound 12c was isolated as a white solid. Yield 67percent, mp>300°C. 1H NMR (200MHz, DMSO-d6) delta: 14.00 (br s, 1H); 8.64 (s, 1H); 8.14?8.10 (m, 2H); 7.55 (m, 3H); 4.26 (q, J=7.0Hz, 2H); 1.28 (t, J=6.8Hz, 3H)

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, 5-Phenyl-1H-1,2,4-triazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Aghazadeh Tabrizi, Mojgan; Baraldi, Pier Giovanni; Ruggiero, Emanuela; Saponaro, Giulia; Baraldi, Stefania; Poli, Giulio; Tuccinardi, Tiziano; Ravani, Annalisa; Vincenzi, Fabrizio; Borea, Pier Andrea; Varani, Katia; European Journal of Medicinal Chemistry; vol. 113; (2016); p. 11 – 27;,
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. 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H8N4

General procedure: 3-Amino-1,2,4-triazole 8a?f (1.0 mmol), o-hydroxybenzaldehyde9a?e (1.0 mmol), acetone (10) (0.22 ml,3.0 mmol), and abs. EtOH (2 ml) were mixed in amicrowave process vial, and then 4 N solution of HCl indioxane (0.07 ml, 0.3 mmol) was added. The mixture wasirradiated at 150°C for 30 min. The reaction mixture wascooled by an air flow and stirred for 24 h at roomtemperature for complete precipitation of the product. Theprecipitate was filtered off, washed with EtOH (1 ml) andEt2O (3×1 ml), and dried. Compounds 1a?w were obtainedin a form of white solids.

The synthetic route of 4922-98-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guemue?, Mustafa K.; Gorobets, Nikolay Yu.; Sedash, Yuriy V.; Chebanov, Valentin A.; Desenko, Sergey M.; Chemistry of Heterocyclic Compounds; vol. 53; 11; (2017); p. 1261 – 1267; Khim. Geterotsikl. Soedin.; vol. 53; 11; (2017); p. 1261 – 1267,7;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 423165-07-5,Some common heterocyclic compound, 423165-07-5, name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, molecular formula is C13H22N4, 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 an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C. N?-{2-Chlorophenyl)-[3-(3-isopropyl-5-methyl-[1,2,4]-triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]methyl}hydrazinecarboxamide (4a): White solid, yield: 75.85 %, m.p. 230-232 C. IR (KBr, numax, cm-1): 3464, 3242, 3151, 3060, 2987,1722, 1654, 1591, 1510, 1415, 1344, 1278, 1219, 1157, 1093,1051, 1033, 918, 852, 736, 627. 1H NMR (DMSO-d6, 400 MHz):delta10.49 (s, 2H, -NH2, D2O exchangeable), 8.26 (s, 1H, chiralproton), 8.15-8.18 (m, 1H, Ar-H, J1= 6.023 Hz, J2= 3.51 Hz),7.47-7.49 (m, 1H, Ar-H, J1= 5.27 Hz, J2= 3.26 Hz, J= 7.027Hz),7.368-7.397 (m, 2H, Ar-H, J2= 3.514Hz, J2= 6.023 Hz),6.589 (br, s, 2H, -2NH), 3.789 (s, 3H,-CH3), 3.46 (m, 1H, Ha),3.31-3.36 (1H, m, J= 9.53 Hz), 2.668-2.677 (m, 2H, J= 1.757Hz), 2.326-2.335 (m, 2H, J= 1.757 Hz), 1.88-1.97 (m, 4H, J1= 1.225 Hz, J2= 2.008 Hz), 1.253-1.236 (d, 6H, 2 × CH3, J=7.027 Hz); 13C NMR: 8.1 (CH3), 24.4 (2 × CH3), 28.4 (2 ×CH2), 26.3 (1CH)-isopropyl), 31.8 (1CH), 36.6 (2 × CH2), 52.7(2 × CH), 65.2 (1CH, adjacent to arom. ring), 126.3, 128.4,128.6, 130.4, 136.7, 137.3 (6C-arom. ring), 158.8 (-C=O,amide), 163.7 (2C, imine (C=N)). Mass: m/z: 429 (M-2), 391((M-2)-isopropyl), 414 ((M-2)-NH3), 301, 309, 279.

The synthetic route of 423165-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Viveka, T. Lakshmi; Sharada, L. Nalanda; Asian Journal of Chemistry; vol. 30; 9; (2018); p. 2029 – 2034;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics