Day: March 17, 2021

These common heterocyclic compound, 7343-33-1, name is 5-Bromo-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. HPLC of Formula: C2H2BrN3

A mixture of (f?)-A/-(piperidin-3-yl)-2-(pyrazolo[1 ,5-a]pyridin-3-yl)pyrimidin-4-amine (Preparation 34, 298 mg, 1.01 mmol) and 3-bromo-1H-1,2,4-triazole (75 mg, 0.51 mmol, prepared as described in Journal of Medicinal Chemistry, 2004, 47 (19), 4645- 4648) was heated at 150 ¡ãC overnight. The crude mixture was purified by reverse phase chromatography (C-18 silica from Waters.(C)., water/acetonitrile/methanol as eluents [0.1percent v/v formic acid buffered] 0percent to 100percent) to give the title compound (96 mg, 52percent) as a white solid.LRMS (m/z): 362 (M+1)+.1H NMR delta (300 MHz, DMSO-d6): 1.5 (d, 1 H), 1.7 (ms, 1 H), 1.8 (m, 1 H), 2.0 (m, 1 H), 2.8 (m, 1H), 3.0 (m, 1 H), 3.4 (m, 1 H), 3.7 (m, 1 H), 4.2 (m, 2H), 6.3 (bs, 1 H), 7.0 (t, 1 H), 7.3 (m, 1 H), 7.4 (m, 1H), 8.1 (m, 1 H), 8.2 (s, 1 H), 8.5 (m, 1 H), 8.6 (s, 1 H), 8.8 (d, 1 H).

The synthetic route of 5-Bromo-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; BACH TA?A, Jordi; PAGES SANTACANA, Lluis, Miquel; TALTAVULL MOLL, Joan; EASTWOOD, Paul, Robert; GONZALEZ RODRIGUES, Jacob; GIULIO MATASSA, Victor; WO2011/101161; (2011); 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. category: Triazoles

To 2H-I,2,3-triazoe (2.0 g, 29 rnmo) n DMF (145 mL) was added NaH (116 g, 29 mmo, 60/b n mnera o) at RT and the mixture was sfirred for lh. After coohng to 0C, 2-choro-I-fluoro-4-ntrobenzene (4.6 g, 26.1 rnmo) was added and the reacUon mixture was stirred at 0C for l.5h, then at RT for I.5h. The mixture was quenched with water and extracted with AcOEt, The organic phase was washed with water and brine, dried over Na2SO4, fitered and concentrated. The crude product was purified by sihca g& co?umn (heptane/AcOEt: 90/10 to 50/50) to afford 2-(2-choro-4-nitropheny)-2 H-. 1,2,3- triazoe. M/z = 225-227 [M+H]+, Rt = 095 mm (UPLC Method 83).

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; NOVARTIS AG; PISSOT SOLDERMANN, Carole; QUANCARD, Jean; SCHLAPBACH, Achim; SIMIC, Oliver; TINTELNOT-BLOMLEY, Marina; ZOLLER, Thomas; (161 pag.)WO2015/181747; (2015); 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. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., SDS of cas: 7343-33-1

Sodium hydride (1.2eq) was added to a solution of 3-bromo-lH-[l,2,4]triazole (leq) in dry DMF (2.3ml/mmol) at 00C and under an atmosphere of nitrogen The solution was stirred at 00C for 20min, then, SEM-Cl (1.2eq) was added. The mixture was stirred at room temperature overnight and diluted with H2O and ethyl acetate. The organic layers was washed with H2O then brine, dried on anhydrous Na2SO4, filtered and concentrated in vacuum to give the titled compound. Crude compound 3- bromo-l-(2-trimethylsilanyl-ethoxymethyl)-lH-[l,2,4]triazole was engaged in step 2 without purification. IH-NMR (CDCl3): delta (ppm) 0.00 (t, 9H); 0.92 (t, 2H); 3.64 (t, 2H); 5.44 (s, 2H); 8.13 (s, IH)

The synthetic route of 7343-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIVALIS; BERECIBAR, Amaya; GUEDAT, Philippe; MOHAMED-ARAB, Celine; WO2011/4017; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 74205-82-6, 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. 74205-82-6 name is (1H-1,2,4-Triazol-1-yl)methanol, 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.

General procedure: A mixture containing 25 ml of acetonitrile, two equivalents of (3,5-dimethyl-1H-pyrazol-1-yl) methanol (compound 2), and one equivalent of N,N-Diethyl-propanediamine was stirred at room temperature for 4 days. Next, the solvent was concentrated at a reduced pressure, washed with brine and dichloromethane. The organic solution was dried with MgSO4, and the solvent was concentrated at reduced pressure to yield compound 3 as light yellow oil.

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

Reference:
Article; Bendaha, Hasnae; Yu, Lisa; Touzani, Rachid; Souane, Rachid; Giaever, Guri; Nislow, Corey; Boone, Charles; El Kadiri, Sghir; Brown, Grant W.; Bellaoui, Mohammed; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4117 – 4124;,
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. 151899-62-6, name is 3-Iodo-1-trityl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Iodo-1-trityl-1H-1,2,4-triazole

Step 2: Preparation of 5-(3-chloro-4-fluorophenyl)-3-methyl-3-(pyrimidin-5-ylmethyl)-l-(l- trityl-l,2,4-triazol-3yl)-l,3-dihydro-2H-indol-2-oneTo 5-(3-chloro-4-fluorophenyl)-3-methyl- 1 -pyrimidin-2-yl- 1 ,3-dihydro-2H-indol-2-one (648 mg, 1.76 mmol), l-trityl-3-iodo-l,2,4-triazole (809 mg, 1.85 mmol, prepared using similar procedures as described in US Pat. No. 5,393,732 incorporated herein by reference in its entirety. Potassium carbonate (1071 mg, 7.75 mmol), N, N’-dimethylethylenediamine (0.300 mL, 2.82 mmol) and copper (I) iodide (268 mg, 1.41 mmol) under nitrogen was added toluene (15 mL).The mixture was stirred at 100 0C for 18 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 25S, eluting with 0-100% ethyl acetate/hexanes, to afford -(3-chloro-4- fluorophenyl)-3-methyl-l-pyrimidin-2-yl-l,3-dihydro-2H-indol-2-one as a white solid. 1H NMR (CDCl3): delta 8.98 (s, 1 H), 8.34 (s, 2 H), 8.04 (s, 1 H), 7.56 (m, 1 H), 7.41 (m, 1 H), 7.30(m, 18 H), 7.05 (d, 1 H, J = 8.3 Hz), 3.31 (d, I H1 J = 13.7 Hz), 3.12 (d, I H1 J = 13.8 Hz) 1.59 (s,3H)MS: m/e 699.24 (M + Na)+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 151899-62-6.

Reference:
Patent; MERCK & CO., INC.; WO2009/45386; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 15294-81-2, 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 15294-81-2 as follows.

A mixture of 4,5-dibromo-1,2,3-triazole (1.0 mmol, 227 mg) and Na2SO3 (3.0 mmol, 378 mg) in water (3.0 mL) was stirred at 100 C (hot plate) for 3 days. The mixture was cooled to rt, then extracted with ethyl acetate (5 mL x 2). The combined extract was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was crystallized from ethyl acetate and heptane to give the desired product as a white solid (99 mg, 67% yield). 1H NMR (400 MHz, DMSO-d6) delta 8.10 (s, 1H) ppm. 13C NMR (100 MHz, DMSO-d6) delta 130.6, 120.5 ppm. HRMS calculated for [C2H2BrN3+H]+ 147.9505, found: 147.9502.

According to the analysis of related databases, 15294-81-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sakurada, Isao; Tetrahedron Letters; vol. 58; 32; (2017); p. 3188 – 3190;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application 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.

lH-l,2,3-triazole-4-carboxylic acid (15.9 mg, 141 muiotaetaomicron) and HATU (53.5 mg, 141 muiotaetaomicron) were dissolved in DMF (2 mL) and stirred for 15 minutes at room temperature. (2R,^R)-4-Amino-2-azido-5-(5′-chloro-2′-fluorobiphenyl-4-yl)pentanoic acid ethyl ester (50 mg, 128 muiotaetaomicron) and DIPEA (67 mu^, 384 muiotaetaomicron) were added, and the mixture was stirred at room temperature for 15 minutes then concentrated in vacuo and the residue was dissolved in EtOH (2 mL). An aqueous solution of IN NaOH (1.3 mL, 1.3 mmol) was added, and the mixture was stirred at room temperature for 30 minutes then concentrated in vacuo and the residue was purified by reverse phase chromatography to yield Compound 1 (45 mg).

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.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 956317-36-5,Some common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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 solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), CsCO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dimethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-2, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. A solution of the acid (3.56 g, 17.52 mmol) in 150 mL of DCM was stirred and cooled to 00C. The solution was treated with oxalyl chloride (1.9 mL, 21.9 mmol) and DMF (68 muL, .878 mmol). The solution was slowly warmed to room temperature and stirred overnight. Solvent was concentrated and the resulting solid was azetroped with DCM and concentrated to provide A-4 as a yellow solid.

The synthetic route of 956317-36-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; FLORES, Broc; SCHREIER, John, D.; WO2010/48016; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 1455-77-2,Some common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, 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: A suspension of 3,5-diamino-1,2,4-triazole (0.1 g, 1 mmol) in absolute EtOH (10 mL) was added to a stirring solution of azo-coupled precursors, Ia-IVa, (2 mmol) in absolute EtOH (50 mL) during a period of 10 min at 60-70 ¡ãC. The mixture was heated in water bath for 15 h at 80 ¡ãC with stirring. The mixture was filtered whilst hot and the obtained solid was washed with hot ethanol (three time) and then with diethylether. The resulted product was dried in air.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Diamino-1,2,4-triazole, its application will become more common.

Reference:
Article; Khanmohammadi, Hamid; Erfantalab, Malihe; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 86; (2012); p. 39 – 43;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

815588-93-3, name is 1-Methyl-1H-1,2,4-triazole-5-carboxylic acid, 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. category: Triazoles

[00152] To a stirring solution of 7 (0.315 g, 2.48 mmol) in CH2C12 (60 mL) was added EDCI.HC1 (336 mg, 1.76 mmol), HOBt (297 mg, 2.20 mmol), DIPEA (0.67 mL, 3.67 mmol) and Int-C (0.5 g, 1.47 mmol) at 0¡ãC. The reaction mixture was stirred at RT for 16 h. After consumption of the starting material (by TLC), the reaction mixture was diluted with DCM and washed with water. The separated organic layer was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to obtain crude product. This material was purified bycolumn chromatography followed by prep-HPLC purification to afford Compound D (80 mg, 12percent). H-NMR: (400 MHz, DMSO-d6): delta 8.09 (s, 1H), 4.55-4.51 (m, 1H), 4.08 (d, 2H), 3.97 (s, 2H), 3.87-3.84 (m, 3H), 3.70-3.55 (m, 2H), 3.45 (t, 1H), 3.35-3.31 (m, 2H), 2.75 (s, 3H), 2.27-2.24 (m, 2H), 1.98-1.92 (m, 4H), 1.85-1.84 (m, 2H), 1.19 (d, 3H). LCMS (m/z): 448 [M++l]

The synthetic route of 815588-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NAUREX, INC.; LOWE, John, A.; KHAN, M., Amin; WO2014/120800; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics