Category: Triazoles

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. 7170-01-6

2,3-Dichloro-5-nitropyridine (2 g, 10.36 mmol), 3-methyl-1H-1,2,4-triazole (1.722 g, 20.73 mmol) and Cs2CO3 (6.798 g, 20.73 mmol) were added to DMF (30 mL) and the reaction was stirred at rt for 12 h. The reaction mixture was quenched with water (200 mL). The mixture was extracted with ethyl acetate (100 mL*3). The organic layer was dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The crude residue was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate from 100:0 to 50:50) to afford a mixture of compounds 20a and 20a-1 (780 mg, 31%) as a white solid. A mixture of 3-chloro-2-(3-methyl-i H-i ,2,4-tri-azol- i -yl)-5-nitropyridine, 20a and 3-chloro-2-(5-methyl-i H-i ,2,4-triazol-i -yl)-5-nitropyridine, 20a- i (780 mg, i .63mmol) was dissolved in MeOH (20 mE), and Zn (0) (i.058g, i 6.28 mmol) and aqueous NH4C1 (20 mE) were added.The reaction mixture was stirred at rt for i 6 h. The reactionmixture was filtered though a pad of diatomaceous earth andthe pad washed with ethyl acetate (20 mEx3). Water (50 mE)was added and the organic layer was separated, dried overNa2SO4, filtered and the filtrate was concentrated to drynessto give a crude mixture of compounds 20b and 20b- i (400mg, 59%) as a yellow solid. ?H NMR (400 MHz, METHANOE-d 4) oe ppm 2.43 (s, 3H), 2.85 (d, J=0.66 Hz, iH), 2.99(s, iH), 7.2i-7.23 (m, iH), 7.82 (d, J=2.65 Hz, iH), 7.86(dd, J=4.85, 2.43 Hz, iH), 8.02 (s, iH), 8.6i-8.65 (m, iH),8.63 (s, iH).10965] A mixture of compounds 5-chloro-6-(3-methyl-1 H-i ,2,4-triazol- i -yl)pyridin-3-amine, 20b and 5-chioro-6- (5-methyl-i H-i ,2,4-triazol- i -yl)pyridin-3-amine, 20b- i (iOO mg, 0.3i mmol), i-(isoquinolin-4-yl)-5-(trifluorom- ethyl)-iH-pyrazole-4-carboxylic acid, 4c (263.0 mg, 0.63 mmol), and pyridine (62.0 mg, 0.78 mmol) were dissolved in dichioromethane (iO mE), and P0C13 (96.2 mg, 0.63 mmol) was added. The mixture was stirred at rt for 2.5 h. Sat. aqueous NH4C1 (20 mE) was added and the mixture was extracted with dichloromethane (20 mEx2). The combined organic layers were dried over Na2504, filtered, and the filtrates were concentrated under reduced pressure to afford a crude yellow oil. The crude oil was purified by reverse phase HPEC (A: water (0.05% HC1)-CAN, B: MeCN, AB:(48%/52%). The pure fractions were concentrated under reduced pressure and lyophilized to dryness to afford a mixture of compounds 53 and 54 (90 mg). The mixture was separated by Supercritical Fluid Chromatography (0.i% NH3H2O: MEOH. Mobile phase: A: CO2 B: 0.i% NH3H2O:MEOH; AB 75/25).10966] Cpd 53:10967] N-(5-chloro-6-(3-methyl- iH- i ,2,4-triazol-i -yl)pyridin-3-yl)- i -(isoquinolin-4-yl)-5-(trifluoromethyl)- iHpyrazole-4-carboxamide, (37.8 mg, 24.i%) as a white solid. ECMS (ESI) mlz M+i: 498.9. ?H NMR (400 MHz, DMSOd 5) oe ppm 2.34-2.40 (m, 3H), 7.27-7.30 (m, iH), 7.8i-7.90 (m, iH), 7.90-7.97 (m, iH), 8.33-8.4i (m, iH), 8.66-8.72 (m, iH), 8.74-8.82 (m, 2H), 8.86-8.98 (m, 2H), 9.60 (s, iH).10968] Cpd 54:10969] N-(5-chloro-6-(5-methyl-i H-i ,2,4-triazol-i -yl)pyridin-3-yl)- i -(isoquinolin-4-yl)-5-(trifluoromethyl)- iHpyrazole-4-carboxamide (i8.4 mg, 11.7%) as a white solid.ECMS (ESI) mlz M+i: 499.0. ?H NMR (400 MHz, DMSOd 5) oe ppm 2.34-2.37 (m, 3H), 7.23-7.32 (m, iH), 7.82-7.90(m, iH), 7.9i-7.98 (m, iH), 8.06-8.i2 (m, iH), 8.33-8.4i(m, iH), 8.59-8.64 (m, iH), 8.65-8.70 (m, iH), 8.75-8.8i(m, iH), 8.85-8.90 (m, iH), 9.58-9.64 (m, iH).

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

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7411-23-6, 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 7411-23-6 as follows.

To a solution of 3,5-dibromo-lH-l,2,4-triazole (5.00 g, 22 mmol) in CH3CN (50 ml) was added 4-bromo-l-butene (3.27 g, 24 mmol) and DIPEA (4.00 ml, 24 mmol), the resulting solution was then heated at 90 C for 3 h. The r.m. was then cooled and diluted with EtOAc (100 ml), washed with an aq. sat. solution of NaHC03 followed by brine, dried (MgSC^), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel (eluent: Heptane/DCM from 100/0 to 0/100). The product fractions were collected and concentrated in vacuo, yielding 5.55 g of intermediate 60 (89 %).

According to the analysis of related databases, 7411-23-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; DE CLEYN, Michel, Anna, Jozef; VAN BRANDT, Sven, Franciscus, Anna; GIJSEN, Henricus, Jacobus, Maria; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; WO2011/86098; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7411-23-6, name is 3,5-Dibromo-1H-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. 7411-23-6

3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) and Mannich base2p (752 mg, 2.9 mmol) were refluxed for 2 h in EtOH (10 mL). Productwas isolated analogously to compound 4a; yield: 475 mg (59%); colorlesscrystals; mp 199-200 C (EtOH).IR (KBr): 3309, 3240, 1643, 1582, 1539, 1512, 1454, 1427, 1369, 1346,1300, 1261, 1204, 1084, 1045, 930, 810, 775 cm-1.1H NMR (400 MHz, DMSO-d6): delta = 11.46 (s, 1 H, NH), 9.21 (s, 1 H, OH),7.52 (s, 1 , NHCO), 7.22 (d, J = 8.7 Hz, 1 H, Ar), 6.78 (d, J = 8.7 Hz, 1 H,Ar), 5.48 (s, 2 H, CH2N), 3.45 (td, J = 6.9, 2.3 Hz, 2 H, CH2), 3.01 (t, J =6.9 Hz, 2 H, CH2).13C NMR (100 MHz, DMSO-d6): delta = 162.3 (C=O), 150.4 (C), 139.4 (C),132.5 (C), 131.3 (C), 128.8 (C), 125.7 (C), 117.1 (C), 115.0 (CH), 114.5(CH), 110.3 (C), 46.0 (CH2), 41.5 (CH2), 22.8 (CH2).Anal. Calcd for C14H11Br2N5O2: C, 38.12; H, 2.51; N, 15.88. Found: C,38.05; H, 2.46; N, 15.92.

Statistics shows that 7411-23-6 is playing an increasingly important role. we look forward to future research findings about 3,5-Dibromo-1H-1,2,4-triazole.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
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 4928-87-4 as follows. 4928-87-4

1,2,4-triazole-3-carboxylic acid (116 mg, 1.02 mmol) was dissolved in methylene chloride (20 ml) and DMF (5 ml), reacted with EDCI (196 mg, 1.02 mmol) and HOBt (138 mg, 1.02 mmol) for 20 min, and then stirred together with 4b-amino-9b-hydroxy-7-isopropyl-4b,9b-dihydro-5-oxa-indeno[2,1-a]-inden-10-one (300 mg, 1.02 mmol) overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO4 and concentrated in a vacuum. Purification by column chromatography (10% methanol in methylene chloride) afforded the title compound as a white solid. (141 mg, 35%). [0812] 1H-NMR (300 MHz, CD3OD) delta 1.17 (d, J=6.9 Hz, 6H, CH3), 2.85 (sep, J=6.9 Hz, 1H, CH), 6.68 (s, 1H, ArH), 6.90 (d, J=8.0 Hz, 1H, ArH), 7.45 (d, J=7.9 Hz, 1H, ArH), 7.607.97 (m, 4H, ArH), 8.40 (s, 1H, ArH).

According to the analysis of related databases, 4928-87-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN K.U. LEUVEN R & D; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Jung, Young Sik; Lee, Chong Kgo; Kim, Hae Soo; Jeong, Hee Chun; Kim, Pil Ho; Han, Soo Bong; Shin, Jin Soo; Neyts, Johan; Thibaut, Hendrik Jan; US2014/114068; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-33-1, 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. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

(f?)-2-(6-Fluoroimidazo[1 ,2-a]pyridin-3-yl)-N-(piperidin-3-yl)pyrimidin-4-amine (42 mg, 0.13 mmol, Preparation 9b) and 3-bromo-1 H-1 ,2,4-triazole (10 mg, 0.07 mmol, prepared as described in the J. Med. Chem. 2004, 47(19), 4645-4648) are heated overnight at 150 ¡ãC. The crude reaction mixture is directly purified by reverse phase chromatography (C-18 silica from Waters, water/1 :1 acetonitrile-methanol as eluents [0.1percent v/v formic acid buffered] 0percent to 100percent) to obtain the title compound (4 mg, 15percent) as a solid.LRMS (m/z): 380 (M+1)+.1H-NMR delta (CDCIa): 1.8 (m, 2H), 1.9 (m, 1 H), 2.0 (m, 1 H), 3.2 (m, 1 H), 3.3 (m,1 H), 3.7 (m, 1 H), 4.1 (m, 2H), 5.2 (bs, 1 H), 6.1 (m, 1 H), 7.2 (m, 1 H), 7.6 (dd,1 H), 7.8 (m, 1 H), 8.1 (m, 1 H), 8.5 (s, 1 H), 9.8 (m, 1 H).

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; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; BACH TANA, Jordi; PAGES SANTACANA, Lluis Miquel; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; MATASSA, Victor Giulio; WO2011/76419; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, The chemical industry reduces the impact on the environment during synthesis 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, I believe this compound will play a more active role in future production and life.

Intermediate 52: step b 1-(4-(1-methyl-1H-1,2,3-triazole-5-carbonyl)piperidin-1-yl)ethanone A solution of i-memyl-lH-l ,2,3-triazole (0.28 g, 3.37 mmol) in dry THF (3 mL) was cooled in a -78 C bath and -butyllithium (2.5 M in hexanes, 1 .26 mL, 3.15 mmol) was added dropwise over a 20 minute period. The suspension was stirred in the cold bath for 30 minutes and then 1 – acetyl-A’-methoxy-N-methy}piperidine-4-carboxamide (0.74 g, 3.45 mmol, Intermediate 52: step a) dissolved in THF (3 mL) was added dropwise. The resulting suspension was stirred at -78 C for 5 minutes then warmed to 0 C and stirred for an additional 30 minutes. The mixture was warmed to room temperature and stirred for 2,5 hours then quenched with saturated aqueous NH4C . The aqueous mixture was extracted with EtOAc (2 x). The combined EtOAc extracts were dried over Na2S04, filtered, concentrated to dryness and chromatographed (EtOAc/DCM) to provide the title compound.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-1,2,3-triazole. I believe this compound will play a more active role in future production and life.

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; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 4928-87-4

To a reaction of 1/7-1, 2, 4-triazole-3 -carboxylic acid (226 mg, 2.0 mmol) and 3- (trifluoromethoxy)aniline (0.28 mL, 2.1 mmol) in dry DMF (10 mL) was added 1- hydroxybenzotriazole monohydrate (337 mg, 2.2 mmol) and EDC (N-(3- Dimethylaminopropyl)-N’-ethylcarbodiimide) (422 mg, 2.2 mmol) followed by N- methylmorpholine (0.88 mL, 8.0 mmol via syringe). The mixture was stirred at room temperature under nitrogen and the solids were gradually dissolved. The contents were stirred at room temperature for 24.0 h, and then slowly diluted into iced water and extracted with DCM (2 x 50 mL). The DCM phase was washed with ice cold water (2 x 100 mL). The DCM phase was dried over anhydrous Na2S04, concentrated under reduced pressure and chromatographed on silica gel using EtOAc and Hexanes (50:50) as eluents to get the desired amide 5 (123.8 mg, 23 % yield) as a white solid. -NMK (400 MHz, DMSO-de): <514.89-14.74 (m, 1H), 10.82 (br s, 1H), 8.67 (br s, 1H), 8.00 (br s, 1H), 7.88 (d, J= 8 Hz, 1H), 7.49 (t, J= 8.2 Hz, 1H), 7.11 (d, J= 8 Hz, 1H); 19F-NMR (376 MHz, DMSO-de): <5 -56.69 ppm. MH+ = 273.2 m/z. 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, 4928-87-4, other downstream synthetic routes, hurry up and to see. Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; NATIONAL JEWISH HEALTH; WEMPE, Michael Fitzpatrick; VAZQUEZ-TORRES, Andres; DAI, Shaodong; (72 pag.)WO2020/41556; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8,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.

2-(2H-1.2,3-triazol-2-yl>5-methylbenzoic acid (A-3)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 1200C 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 Na2SO^ filtered and concentrated. The residue was purified by gradient elution on Sitheta2 (0 to 10% MeOH in water with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-3, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. Data for A-3 : 1HNMR (500 MHz, DMSO-d6) d 12.98 (br s , IH), 8.04 (s, 2H), 7.72-7.45 (m, 3H), 2.41 (s, 3H) ppm.

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

Reference:
Patent; MERCK & CO., INC.; WO2008/8518; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

61-82-5, 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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine, A new synthetic method of this compound is introduced below.

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.

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

16681-65-5, Name is 1-Methyl-1H-1,2,3-triazole, 16681-65-5, 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.

intermediate 6: step a(1-methyl-1H-1,2,3-triazol-5-yl)(1-methyl-1H-imidazol-5-yl)methanolA solution of 1 -methyl- lH- l ,2,3-triazole (1 .47 g, 17.7 mmol, PCT Int. Appl. 2008098104) in 20 mL THF was cooled to -40 C in a dry-ice/acetonitrile bath. -Butyllithium (1.6 M in hexane, 10.2 mL, 16.3 mmol) was added dropwise via syringe and the mixture was stirred at -40 C for 30 minutes. A solution of 1 -methyl- 1 H-imidazole-5-carbaldehyde (1.50 g, 13.6 mmol) in 10 mL THF was then added and the mixture was stirred for 5 minutes, then was transferred to an ice/water bath. After 1 hour, the mixture was quenched by addition of saturated aqueous NPLCl, diluted with water, and extracted twice with EtOAc. The aqueous phase, which contained the title compound, was then concentrated. The residue wras purified by flash column chromatography (silica gel, gradient 3-10% MeOH-DCM) to afford the title compound as a light yellow foam.

Statistics shows that 1-Methyl-1H-1,2,3-triazole is playing an increasingly important role. we look forward to future research findings about 16681-65-5.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; 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.; LEONARD, Kristi, A.; WO2015/57203; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics