Tag: M.W=0-100

Some common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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

General procedure: 20 mg of gamma-Fe2O3Ph-PMO-NaHSO4 was added to a roundbottomflask containing an aromatic aldehyde (1 mmol), 3-amino-1,2,4-triazole 2 (1.0 mmol), b-diketones (dimedone 3, 1,3-cyclohexadione 4 or ethyl acetoacetate 5) (1.0 mmol) and stirredunder solvent-free conditions at 100 C in certain times. Meanwhile,the progress of the reactionwas indicated by TLC (n-hexane:ethyl acetate; 7:3). With completing the reaction, 3ml ethanol waspoured and the magnetic nanocomposite was separated in thepresence of a magnetic stirring bar; the reaction mixture becameclear. The crude product was recrystallized from ethanol to give thepure product. The pure products were characterized by conventionalspectroscopic methods. Physical and spectral data for theselected compounds are represented below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61-82-5, its application will become more common.

Reference:
Article; Haghighat, Mahdieh; Shirini, Farhad; Golshekan, Mostafa; Journal of Molecular Structure; vol. 1171; (2018); p. 168 – 178;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 41253-21-8, These common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, 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.

Example 46: Preparation of eis-4-amino-5-chIoro-N-[l-(3-(lH-l.,2,4-triazol-l- vDpropyr)-3-methoxypiperidin-4-v?-2-methoxybenzamideStep 1: Preparation of l-(3-chloropropyD-lH-l,2,4-triazole1 g of a 1 ,2,4-triazole sodium salt was dissolved in N,N-dimethylforrnamide, and the solution was cooled to 0C, to which 570 mg of 60% sodium hydride (NaH) was then added.The reactants were stirred for 20 min, and 1.3 mL of l-bromo-3-chloropropane was slowly added thereto. The reaction mixture was warmed to room temperature and stirred for 12 hours, followed by addition of water and extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford 600 mg (38%) of the title compound.1H NMR(CDCl3): delta 8.08(s, IH), 7.93(s, IH), 4.37-4.34(m, 2H), 3.47-3.43(m, 2H), and 2.35-2.29(m, 2H)

The synthetic route of 41253-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DONG-A PHARM. CO., LTD.; WO2008/114971; (2008); 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Methyl-1H-1,2,4-triazole

The solution of compound 1 (30 g, 0.13 mol) in THF (1.5 L) was cooled to -78 C. Then a solution of vinyl magnesium in THF (508 mL, 1N, 0.51 mol) was added dropwise to the above solution maintained below -40 C. The mixture was stirred for 3 hrs at -78 C before being quenched with saturated aqueous NH4Cl solution. The layers were separated, the aqueous layer was extracted with EtOAc (3¡Á500 mL) and the combined organic layer was washed with brine and concentrated. The crude product was purified by silica gel column chromatography to obtain compound 2 (5 g, 17%). Compound 2 (4.0 g, 17.2 mmol) was dissolved in freshly prepared NaOMe (20 mL). CuI (3.2 g, 17.2 mmol) was added to the above solution. The mixture was stirred at 110 C under microwave for 3 hrs. After the mixture was completed, the mixture was added EtOAc and H2O, then the suspension was filtered, the filtrate was separated. The organic layer was concentrated to give crude product which was purified by column chromatography to give compound 3 (1.8 g, 45%). A mixture of compound 3 (0.7 g, 3.8 mmol) and 3-methyl-1,2,4-triazole (6.4 g, 76.8 mmol) was added copper powder (0.49 g, 7.68 mmol) and KOH (0.43 g, 7.68 mmol). The mixture was heated tomelt at 170-175 C under N2. After the starting material was consumed completely, the mixture was added EtOAc and H2O, then the suspension was filtered, the filtrate was separated. The organic layer was concentrated to give crude product which was purified by column chromatography to give compound 4 (0.23 g, 26%). A solution of compound 4 (0.23 g, 1 mmol) in THF (12 mL) was cooled to -10 C, EtMgBr (0.47 g, 3.5 mmol)was added dropwise at -10 C followed by the addition of pyridine(0.3 mL). The slurry was cooled to -45 C, and the ethyl 2-chloro-2-oxoacetate (0.55 g, 4 mmol) was added dropwise at -45 C. The slurry was allowed to -10 C and stirred at this temperature for 1h. After the reaction was completed, the mixture was quenched with IPA (2mL) and H2O (20 mL). The mixture was extracted with EtOAc, the organic layer was washed with brine and concentrated to give crude product which was purified by column chromatographyto give compound 5 (0.17 g, 52%). A solution of compound 5 (0.17 g, 0.52mmol) in MeOH (5 mL) was added NaOH (0.041 g, 1.03 mmol) and H2O (2mL). The mixture was stirred at 25 C for 6 hrs and then added 1N HCl to adjusted pH 6, the mixture was concentratedto give compound 6 (0.29 g) as crude product.

The synthetic route of 7170-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tuyishime, Marina; Lawrence, Rae; Cocklin, Simon; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 228 – 234;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, 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

A mixture of 7-bromo-5-nitroisoquinolin-1(2H)-one (293b, 4.00 g, 14.9 mmol), 1,4-dimethyl-1H-1,2,3-triazole (2.17 g, 22.3 mmol), palladium acetate (334 mg, 1.49 mmol), CatacXiumA (butyl di-1-adamantylphosphine) (1.10 g, 2.97 mmol), and potassium acetate (7.30 g, 74.3 mmol) in 2-methyl-2-butanol (100 mL) was degassed with nitrogen, and heated at 120 C. in a sealed tube overnight. After cooling down room temperature, the reaction mixture was partitioned between ethyl acetate (300 mL) and water (300 mL). The organic phase was separated, washed with brine (1*300 mL), dried over sodium sulfate, concentrated to dryness, and purified by silica gel chromatography (eluting with a gradient of 0%-10% methanol in ethyl acetate), affording 7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one (293c, 2.55 g, 60% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) delta 11.95 (br. s., 1H), 8.57 (s, 2H), 7.55 (d, J=5.38 Hz, 1H), 6.98 (d, J=7.34 Hz, 1H), 4.00 (s, 3H), 2.29 (s, 3H). MS: 284 [M-1].

The synthetic route of 60166-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; EDWARDS, Martin Paul; KUMPF, Robert Arnold; KUNG, Pei-Pei; MCAPLINE, Indrawan James; NINKOVIC, Sacha; RUI, Eugene Yuanjin; SUTTON, Scott Channing; TATLOCK, John Howard; WYTHES, Martin James; Zehnder, Luke Raymond; US2014/179667; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route 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 solution of 3-methyl-1H-1,2,4-triazole (7.3 g, 88 mmol) in DMF (75 mL) was added K2CO3 (60.7 g, 439 mmol) and 2-bromopropionic acid tert-butyl ester (14.6 mL, 88 mmol). The reaction was stirred at room temperature overnight. The mixture was diluted with EtOAc (500 mL), washed with water (¡Á3) then brine. Dried over MgSO4 and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/isohexane (20 to 100%) to give 13 g of crude product as a 3:1 mixture of regioisomers. The mixture was purified by Chiralcel OD with a gradient from 4% to 30% IPA/Heptane. Then the first two peaks were separated with Chiracel OD column isocratically eluting with 4% IPA/Heptane. The second peak was collected as the desired single stereoisomer (R or S) (2-(3-methyl-1H-1,2,4-triaol-1-yl)propanoic acid tert-butyl ester) (3.5 g, 19%). 1H-NMR (500 MHz, CDCl3) delta 8.05 (s, 1 H), 4.90 (q, J=7 Hz, 1 H), 2.35 (s, 3 H), 1.72 (d, J=7 Hz, 3 H), 1.40 (s, 9 H). ESI-MS calculated for C10H17N3O2: Exact Mass: 211.13; Found 156.05 (-tBu).

The synthetic route of 7170-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berger, Richard; Chang, Lehua; Edmondson, Scott D.; Goble, Stephen D.; Ha, Sookhee Nicole; Kar, Nam Fung; Kopka, Ihor E.; Li, Bing; Morriello, Gregori J.; Moyes, Chris R.; Shen, Dong-Ming; Wang, Liping; Zhu, Cheng; US2009/253705; (2009); 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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C2H4N4

A mixture of aldehyde (1 mmol), dimedone (1 mmol), 3-amino-1,2,4-triazole (1 mmol), and [C4(H-DABCO)2][HSO4]4 (16 mg) washeated in an oil bath (90 C) under solvent-free conditions. Aftercompletion of the reaction, as identified by TLC, using n-hexane:EtOAc (7:3) as the eluent, 10 mL of water was added and stirredfor 10 min. The catalyst was dissolved in water and the solid wasfiltered off and washed with warm EtOH, to obtain the pure targetmolecule.

The synthetic route of 61-82-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Safari, Niloufar; Shirini, Farhad; Tajik, Hassan; Journal of Molecular Structure; vol. 1201; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16681-65-5, name is 1-Methyl-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. category: Triazoles

To a flask containing 1-methyl-1H-1,2,3-triazole (430 mg, 0.8 mmol) was added THF (15 mL) and the solution was cooled to -43 C. using a CH3CN-CO2 bath. Then, n-BuLi, (2.5 M in hexanes, 0.7 mL, 1.75 mmol) was added dropwise. The reaction mixture was stirred at -40 C. for 30 minutes, then tert-butyl-3-(4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline-6-carbonyl)-azetidine-1-carboxylate (430 mg, 0.8 mmol, Intermediate 61: step b) in 2 mL THF was introduced. The reaction mixture was allowed to warm to room temperature over 30 minutes, and was quenched after 45 minutes with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (3*30 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on Silica gel (10% acetone-hexane increasing to 30% acetone) afforded the title compound as a white amorphous solid. 1H NMR (500 MHz, CDCl3) delta 8.24 (d, J=2.1 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.56-7.47 (m, 3H), 7.40 (d, J=8.1 Hz, 2H), 7.35 (dd, J=8.7, 2.1 Hz, 1H), 4.35 (s, 2H), 4.20 (t, J=8.8 Hz, 1H), 4.07 (s, 3H), 4.00 (dd, J=9.3, 5.6 Hz, 1H), 3.92 (dd, J=8.9, 5.7 Hz, 1H), 3.67 (s, 3H), 3.62 (t, J=8.8 Hz, 1H), 3.52-3.38 (m, 1H), 1.38 (s, 9H); MS (ESI): mass calcd: Chemical Formula: C30H31ClF3N5O4; Exact Mass: 617.2. m/z found 617.8 [M+H]+.

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

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

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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., COA of Formula: C3H5N3

General procedure: TBHP (3 eq.) was added to a solution of 3-phenyl-1,2,4-triazole (0.4 mmol) 1a, benzaldehyde 2a (0.6 mmol), followed by TBAI (20 mol%) in DCE(4 mL). The reaction mixture was stirred at 120 oC under nitrogen atmosphere for 5 h. After completion of the reaction confirmed by TLC, the reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic and aqueous layers were then separated and aqueous layer was extracted with ethyl acetate twice. The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude. The crude was further purified by silica gel chromatography using EtOAc/hexane as eluents to furnish the desired product 3 or 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:
Article; Agisho, Habtamu Abebe; Esatu, Habdolo; Hairat, Suboot; Zaki, Mehvash; Tetrahedron Letters; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. HPLC of Formula: C2H5N5

3-Amino-6-chloro-1,2,4,5-tetrazine (4) (1:00 g, 7.60mmol) was dissolved in a mixture of 16:0 mL acetonitrile and 2:0 mL water. To the stirred solution 3,5-diamino-1,2,4-triazole (1:51 g, 15:2 mmol) was added. The mixturewas heated to 90 ¡ãC and refluxed for 16 h. The precipitatewas filtered and washed with water and acetonitrile. Theproduct (9) was recrystallized from water. After standing overnight at ambient temperature, the crystals were filteredand dried. 1:33 g (5:78 mmol; 76percent) of red needles of 9 were yielded. ? Elemental analysis (C4H10N10O2, 230.19)exp. (calcd.) in percent: C 20.62 (20.87); H 4.18 (4.38); N 60.37(60.85). ? DSC (5 C min1, ¡ã C): Tdec:: c 314 ¡ãC. ? 1H NMR([D6]DMSO, 25 ¡ãC, ppm): d =5.38 (s, 2H, NH2 triazole),6.94 (s, 2H, NH2 triazole), 7.83 (s, 2H, NH2 tetrazine).? 13C NMR ([D6]DMSO, 25 ¡ãC, ppm): d =155.5 (1C,C-NH2 triazole), 156.3 (1C, C-NH2 triazole), 162.7 (1C,C-tetrazine), 162.9 (1C, C-tetrazine). ? MS ((+)-DEI): m=z = 194.1 (100) [C4H6N10]+, 124.1 (43) [C3H4N6]+,99.1 (5) [C2H5N2]+, 82.1 (19) [C2H2N5]+. ? Raman: n(cm-1)=3250 (2), 3184 (5), 1648 (7), 1570 (5), 1555 (12), 1526 (5), 1477 (90), 1399 (4), 1371 (8), 1335 (6), 1158 (10),1027 (18), 866 (100), 828 (4), 669 (7), 580 (9), 456 (5), 356(4), 345 (7), 321 (6). ? Sensitivity data: IS: > 40 J; FS: >360 N; ESD: > 1 J.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1455-77-2, its application will become more common.

Reference:
Article; Klapoetke, Thomas M.; Preimesser, Andreas; Stierstorfer, Joerg; Zeitschrift fur Naturforschung, B: Chemical Sciences; vol. 68; 12; (2013); p. 1310 – 1320;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-34-2, name is 3,5-Dimethyl-4H-1,2,4-triazole, 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. HPLC of Formula: C4H7N3

General procedure: To a solution of 1-(3-chloropyridin-2-yl)piperidine-4-carboxylic acid (0.61 mmol) andamine/aniline (0.73 mmol, 1.2 eq.) in DMF (4 ml) was added TBTU, (alternatively HATU or EDCI)(0.92 mmol, 1.5 eq.) and diisopropyl ethylamine (1.8 mmol, 3.0 eq.). The reaction mixture wasstirred at room temperature until completion of the reaction. The reaction mixture was dilutedwith ethyl acetate and washed with 1N HCl, water and brine. The organic phase was dried oversodium sulfate, filtered and concentrated. The crude material was purified by columnchromatography or preparative HPLC (C18, acetonitrile/water gradient).

The synthetic route of 7343-34-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Schlapbach, Achim; Revesz, Laszlo; Pissot Soldermann, Carole; Zoller, Thomas; Regnier, Catherine H.; Bornancin, Frederic; Radimerski, Thomas; Blank, Jutta; Schuffenhauer, Ansgar; Renatus, Martin; Erbel, Paulus; Melkko, Samu; Heng, Richard; Simic, Oliver; Endres, Ralf; Wartmann, Markus; Quancard, Jean; Bioorganic and Medicinal Chemistry Letters; vol. 28; 12; (2018); p. 2153 – 2158;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics