Triazoles

Electric Literature of 7170-01-6, A common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, molecular formula is C3H5N3, 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 mixture of the intermediate 5 500 mg, 60% sodium hydride (dispersion in paraffin liquid) 60 mg and N,N-dimethylformamide 2.5 mL was added 3-methyl-1H-1,2,4-triazole (which was prepared by a method described in US 2006/0293304 A1) 113 mg. The mixtures were stirred at 0C for 2.5 hours. To the reaction mixture was then added saturated aqueous sodium hydrogen carbonate solution and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and brine and dried over anhydrous sodium sulfate. The resulting organic layers were concentrated under reduced pressure. The resulting residues were subjected to a silica gel colunm chromatography to give the present compound 4 153 mg. H1-NMR (CDCl3) delta: 9.03 (1H, s), 8.80 (1H, br s), 8.68 (1H, d), 8.35 (1H, br s), 8.22 (1H, d), 3.92 (3H, s), 3.81 (2H, q), 2.54 (3H, s), 1.39 (3H, t).

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; Sumitomo Chemical Company, Limited; TANABE, Takamasa; MIZUNO, Hajime; OKAMOTO, Hiroshi; (41 pag.)US2017/135348; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 184177-83-1, These common heterocyclic compound, 184177-83-1, name is 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one, 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.

2-[(l S2S)-l-Ethyl-2-benzyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-l- piperozinyl] phenyl]-3H-l,2,4-triazol-3-one (1 kg) was added to the Flask along with Dimethylsulfoxide (8 lit) at room temperature and stirred for 15 min. Solution of Sodium hydroxide (0.15 kg) in Water (0.3 lit) was added and maintained for 1 hr and ((3S,5R)-5-((lH-l,2,4-triazol-l-yl) methyl)-5-(2,4-difluorophenyl)- tetrahydrofuran-3-yl)methyl-4-nitrobenzene sulfonate (1.2 kg) was added and maintained for 4-5 hrs. Water (10 lit) was added to the reaction mixture and stirred for 15 min. Ethyl acetate (7.5 lit) was added and stirred for 15 min. Aqueous layer and Ethyl acetate layer were separated and aqueous layer was extracted with Ethyl acetate (3 lit). Aqueous layer and Ethyl acetate layer were separated and total Ethyl acetate layer was washed with Water (5 lit) and brine solution. Ethyl acetate layer was dried with Sodium sulfate and distilled under vacuum at below 50C. The resultant crude was treated with Isopropyl alcohol (10 lit) and heated to 75-80C. The resultant mass was cooled to room temperature, maintained for 2 hrs, filtered the solid and washed with Isopropyl alcohol (1 lit).Yield: 1.3Kg; HPLC: 98.46%.

Statistics shows that 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one is playing an increasingly important role. we look forward to future research findings about 184177-83-1.

Reference:
Patent; METROCHEM API PVT LTD.; NANDEPU, Venkateswara Rao; BIJJULA, Venkata krishna Reddy; BATHINA, Satyanarayana; (44 pag.)WO2019/77627; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

[0850] 3H-1,2,3-triazole-4-carboxylic acid (3.4 mg, 30f.tmol) was combined with HATU (11 mg, 30 f.tmol) in DMF(0.3 mL) and stirred at room temperature for 10 minutes;DIPEA (1 eq.) was added and the mixture was stirred for 1minute. Compound2 (lOmg, 30 f.tmol) inDMF (0.5 mL)wascombined with DIPEA (5.2 f.LL, 30 f.tmol), then added to theactivated acid solution. The resulting solution was stirred atroom temperature for 30 minutes; LC/MS showed the mass ofthe desired product. The solvent was removed in vacuo andthe crude residue was purified by reverse phase chromatographyto yield Compound a (6.1 mg) as a TFA salt. MS rn/z[M+Ht calc’d for C27H31CIFN50 4 , 544.21; found 545.2.

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

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

Reference of 7343-33-1, 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 7343-33-1 as follows.

A mixture of 3-brom-1, 2, 4-lH-triazole (prepared as described in Chemische Berichte 1967, 100, 2250) (1.0 g, 6.76 mmol), tri (4- fluorophenyl) bismuth acetate (prepared by the method described in Synthetic Communications 1996,4569) (4.53 g, 7.4 mmol), copper (II) acetate (0.25 g, 20molpercent) and N, N, N’, N’-tetramethylguanidine (1.7 mL, 13.5 mmol) in dry tetrahydrofuran (30 mL) was stirred at 50OC under a balloon of air for 16 hr. The suspension was poured into water (100 mL) and 1M citric acid (30 mL) to give a suspension of pH 3-4. Ethyl acetate (100 mL) was added and the mixture was filtered through Celite , washing the filter cake with ethyl acetate (100 mL). The two phases of the filtrate were separated and the organic layer was dried (Na2SO4) and concentrated. Flash column chromatography on silica gel, eluting with 25percent then 40percent ethyl acetate-isohexane, gave 1- (4-fluorophenyl)-3-bromo- 1,2, 4-lH-triazole as an off-white solid (0.74 g, 45percent). 8 (iH, 400MHz, CDCl3) 7.18-7. 24 (2H, m), 7.60-7. 65 (2H, m), 8.37 (1H, s). MS (ES+) 242,244 ([MH] +).

According to the analysis of related databases, 7343-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/93252; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 3641-08-5, 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. 3641-08-5, name is 2H-1,2,4-Triazole-3-carboxamide belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE I Preparation of 1(and 2 and 4)-Acetyl-s-triazole-3-carboxamide A mixture of 0.2 g. of 1,2,4-triazole-3-carboxamide and 0.5 ml. of acetic anhydride is heated on an oil bath at a temperature of 150 C. for 20 minutes. The wet solid mass is triturated with diethyl ether and collected and washed with diethyl ether yielding 0.2 g. of colorless solid. This solid is recrystallized from acetonitrile giving a colorless solid, m.p. 212-215 C. (dec).

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

Reference:
Patent; American Cyanamid Company; US4006159; (1977); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6818-99-1, name is 3-Chloro-1,2,4-triazole, molecular formula is C2H2ClN3, 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-Chloro-1,2,4-triazole

The procedure described in G.B. 1,157,256 was followed: In a 100 ml flask equipped with a mechanical stirrer, a temp probe, a heating mantle, a reflux condenser, and a positive nitrogen set up was placed with 3-chloro-1,2,4-triazole 5.2 gm (50.24 mmoles), NaCN 2.6 gm (53.05 mmoles), and dimethylformamide 55 ml. The mixture was heated to reflux for 16 hours and quenched with 250 ml ice water. The solid was filtered, washed with water, and dried to give a black solid, 0.53 gm (11% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6818-99-1, its application will become more common.

Reference:
Patent; Ampac Fine Chemicals LLC; US2009/292122; (2009); A1;,
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 22300-52-3 as follows. Safety of 4,5-Dibromo-2H-1,2,3-triazole

Step 1 : A mixture of A-24.1 (2.00 g, 1 1 .0 mmol), A-24.2 (3.80 g, 17.0 mmol), Cul (0.13 g, 0.68 mmol), A-24.3 (0.14 mL, 1 .00 mmol) and K2C03 (2.30 g, 17.0 mmol) in dry DMF (10 mL) is heated to 120¡ãC by microwave irradiation and stirred for 40 min. The mixture is poured into water and extracted with Et20. The aq. phase is acidified with HCI (4N aq. solution) and extracted with EA. The combined organic phases are dried and concentrated to give the crude product which is purified by flash column chromatography on silica gel (using a solvent gradient from 100percent EA to EA/MeOH = 9/1 ) to provide 3.6 g of A-24.4. APCI+/-: 365 [M+H]+; HPLC (Rt): 1 .10 min (Method N).

According to the analysis of related databases, 22300-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; (102 pag.)WO2017/178344; (2017); 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1H-[1,2,3]Triazole-4-carboxylic acid

lH-l,2,3-triazole-4-carboxylic acid (9.8 mg, 87 muiotaetaomicron) and HATU (36.4 mg, 96 muiotaetaomicron) were combined in DMF (3.0 mL) and stirred at room temperature for 15 minutes. Compound 2 (40.3 mg, 87 muiotaetaomicron) and DIPEA (46 mu,, 261 muiotaetaomicron) were added and the resulting solution was stirred at room temperature for 15 minutes, after which time LCMS indicated desired product formation. The solvent was removed in vacuo and the crude residue was purified by reverse phase chromatography to yield Compound c (34.5 mg) as a TFA salt. MS m/z [M+H]+ calc’d for C28H3 found 558.

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FLEURY, Melissa; BEAUSOLIEL, Anne-Marie; HUGHES, Adam D.; LONG, Daniel D.; WILTON, Donna A.A.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 288-36-8, name is 1H-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. Product Details of 288-36-8

Intermediate G To a mixture of 2-bromo-4-fluorobenzoic acid (30 g, 137 mmol), cesium carbonate (89.26 g, 274 mmol), and copper(I) iodide (5.27 g, 27.4 mmol) in DMF (200 mL) were added N,N’-dimethylcyclohexane-l,2-diamine (3.7 mL,23.3 mmol) and lH-l,2,3-triazole (18.92 g, 274 mmol). The resulting mixture was stirred at 110 C overnight, cooled, concentrated in vacuo, and diluted with water (150 mL). The aqueous layer was extracted with EtOAc (300 mL x 3). The aqueous layer was acidified with 2 N HC1 and extracted with EtOAc (300 mL x 4). The combined organic layers were washed with brine (150 mL x 3), dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography gel (petroleum ether : EtOAc = 100: 1 – 5 : 1) to provide the title compound as a solid. LRMS m/z (M+H) 208.0 found, 208.0 required.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; LIVERTON, Nigel; LUO, Yunfu; (85 pag.)WO2016/100156; (2016); 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. 81606-79-3, name is 2-(1,2,4-Triazol-1-yl)acetonitrile, A new synthetic method of this compound is introduced below., Product Details of 81606-79-3

Step 1: l-(5-((4H-l,2,4-Triazol-4-yl)methyl)-2-(difluoromethoxy)benzyl)-6-bromo-2-meth l-l,2- dihydro-3H-indazol-3-one A mixture of 6-bromo- 1 -(5-(bromomethyl)-2-(difliioromethoxy)berizr ‘l)-2-methyl- 1 ,2-dihydro-3H- indazoi-3-one (Preparation 20, step 3) (0.100 g, 0.210 mmol) and 2-(lH-l,2,4-triazol-l-yl)acetonitrile {Synthesis 1995, 9, 1183-1189) (0.026 g, 0.210 mmol) in MeCN (1 mL) was heated at about reflux for about 6 h, after which additional 2~(lH-l,2,4-triazoi-l-yl)acetonitrile (0.020 g, 0.164 mmol) was added and heating continued for about 24 h. The reaction mixture was concentrated under reduced pressure and the residue was treated with 2 M aq. sodium hydroxide (2 mL, 4 mmol). After stirring for about 1 h, the mixture was extracted with EtOAc (3 x 5 mL) and the combined organic phases were washed with sat. aq. NaCl (5 mL), dried over Na2S04, filtered, and concentrated under reduced pressure. The sample was purified on silica gel using 0-5% MeOH with DCM to give the title compound (0.053 g, 54%); LC/MS (Table A, Method i) = 1.04 min; MS m/z: 464 and 466 X i 11 >

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; ABBVIE INC.; ARGIRIADI, Maria; BREINLINGER, Eric; DIETRICH, Justin, D.; FRIEDMAN, Michael; IHLE, David; MORYTKO, Michael; MULLEN, Kelly; OSUMA, Augustine; LO SCHIAVO, Gloria, Y.; WILSON, Noel, S.; (303 pag.)WO2016/168633; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics