Triazoles

Synthetic Route of 1338226-21-3,Some common heterocyclic compound, 1338226-21-3, name is 3-(Chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one, molecular formula is C4H6ClN3O, 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 75L flask was charged a 9.63wt% solution of 3-(chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one in NMP (11.6 kg,7.55 mol), 3 -chloro-5 -((2-oxo-4-(trifluoromethyl)- 1 ,2-dihydropyridin-3 -yl)oxy)benzonitrile (2.00 kg, 6.29 mol), NMP (3.8 L) and 2-methyl-2-butanol (6.0 L). To the resulting suspension was slowly added N,N-diisopropylethylamine (4.38 L, 25.2 mol) over 4h. The reaction was aged 18h at ambient temperature. The reaction is considered complete when HPLC indicated <1% 3 -chloro-5 -((2-oxo-4-(trifluoromethyl)- 1 ,2-dihydropyridin-3 -yl)oxy)benzonitrileremaining. The tan solution was quenched with acetic acid (1.26 L, 22.0 mol) and aged at ambient temperature overnight. The tan solution was warmed to 70 C. Water (2.52 L) was added and the batch was seeded with anhydrate Form 11(134 g)(procedures for making anhydrate Form II are described in W02014/052171). The thin suspension was aged lh at 70C. Additional water (14.3 L) was added evenly over 7 h. The slurry was aged 2h at 70 C andthen slowly cooled to 20 C over 5 h. The slurry was filtered and washed with 2 :1 NMP/water(6 L), followed by water washes (6 L x 2). The filter cake was dried under N2 to give 2.53 kg(85% yield) of a white solid that was confirmed to be crystalline Form II of the title compoundby X-ray powder defraction analysis. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one, its application will become more common. Reference:
Patent; MERCK SHARP & DOHME CORP.; CAO, Yang; GAUTHIER, Donald, R., Jr.; HUMPHREY, Guy, R.; ITOH, Tetsuji; JOURNET, Michel; QIAN, Gang; SHERRY, Benjamin, D.; TSCHAEN, David, M.; WO2015/84763; (2015); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, name is 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. name: 1H-1,2,3-Triazole

To a stirred solution of compound 54 (5.00 g, 74.55 mmol) in DCM (100 mL) was added 3,4-dihydro-2H-pyran (6.90 g, 82.00 mmol) and p-Toluenesulfonic acid (0.62 g, 3.62 mmol), the mixture was stirred at rt for 16 h, TLC showed that the start materials was consumed up, stopped the reaction, concentrated in vacuo, the residue was purified by column (EtO Ac/Hex 1/10 to 1/6) to give compound 55 (9.00 g, 81% yield) as a colorless oil. MS (ESI) (M/Z): [M+H]+ =154.1; 1H NMR (400 MHz, CDC13) delta 7.67 (s, 2H), 5.73 (dd, 7 = 9.1, 2.7 Hz, 1H), 4.03 (ddd, 7 = 11.7, 3.7, 2.4 Hz, 1H), 3.79 – 3.69 (m, 1H), 2.48 – 2.38 (m, 1H), 2.16 – 2.04 (m, 2H), 1.77 – 1.69 (m, 2H), 1.67 – 1.61 (m, 1H).

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHANG, Hai-Jun; (63 pag.)WO2018/217439; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 118863-62-0,Some common heterocyclic compound, 118863-62-0, name is 3-(4-Bromophenyl)-1H-[1,2,4]triazole, molecular formula is C8H6BrN3, 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.

1.5 g of 3-(4-bromophenyl)-l77-l, 2, 4-triazole prepared in Step 2 was dissolved in (0678) 5.0 mL of N. N-d i m e th y 1 fo rm am i dc . and the resulting reaction mixture was cooled to 0 C. To the reaction mixture, 0.32 g of sodium hydride was added, and then the reaction mixture was stirred for 30 minutes. 1.67 g of (2-(chloromethoxy)ethyl)trimethylsilane was added thereto and the reaction mixture was then stirred at 0C for 15 minutes and additionally stirred at room temperature for 2 hours further. After addition of distilled water, the reaction mixture was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give a residue as a yellow liquid. The residue was purified with silica gel column chromatography (developing solvent: n- hexane/ethyl acetate= 2/1) to give 1.1 g of the title compound as a white solid (yield: (0679) 46.4 %). -NMR (CDCb, 400MHz) d 8.20(s, 1H), 7.8 l-7.79(m, 1H), 7.76-7.74(m, 1H), 7T4(d, 1H), 6.97(d, 1H), 3.96(s, 3H), 3.83(d, 2H), 2T5-2. lO(m, 1H), l.06(d, 6H)

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

Reference:
Patent; YUHAN CORPORATION; HAN, Tae Dong; TAK, Hee Jae; KIM, Eun Kyung; CHOI, Su Bin; PARK, Sol; KIM, Dong Hoon; KIM, So Young; CHOI, Hyun Ho; KIM, Tae Wang; JU, Mi Kyeong; HA, Na Ry; LEE, Eui Chul; (247 pag.)WO2019/180646; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 63666-11-5, 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 63666-11-5 as follows.

A suspension of ethyl 5-amino-lH-l,2,4-triazole-3-carboxylate in acetic anhydride was refluxed for 30 min. Excess acetic anhydride was evaporated. Water was added to the residue and the mixture was stirred overnight. The colourless product was filtered off, washed with water and dried to obtain 0.134 g (53% yield) of the product. 1H-NMR (40 MHz, DMSO-d6): 1.35 (3H. t. OCH2CH3), 2.12 (3H, s, COC), 4.3 (2H, q, OCH2CH3), 11.71 (1H, s, NHCO), 13.74 (1H, s, NH-triazole)

According to the analysis of related databases, 63666-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 4SC DISCOVERY GMBH; LEBAN, Johann; ZAJA, Mirko; WO2014/1464; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4320-91-6, name is 2H-1,2,3-Triazole-2-acetic acid, molecular formula is C4H5N3O2, 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: C4H5N3O2

A round bottom flask was charged with (2S,4R)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide hydrochloride (150 mg, 0.37 mmole, 1 eq), prepared as in Reference 6, 2H-l,2,3-triazole-2-ylacetic acid (51 mg, 0.40 mmole, 1.1 eq), HATU (152 mg, 0.40 mmole, 1.1 eq) and DMF (1 mL). DIEA (195 muL, 1.11 mmole, 3 eq) was added and the mixture stirred at ambient temperature for 18 hours. The reaction mixture was partitioned between ethyl acetate and deionized water. The aqueous layer was separated and extracted twice with ethyl acetate. The combined organics were washed with 5% lithium chloride (3 x 5 mL), IN sodium bicarbonate (2 x 5 mL) and then deionized water (2 x 5 mL) and concentrated in vacuo. Product was purified from the residue via flash chromatography (silica, 5% MeOH, 95% EtOAc). Clean fractions were combined and concentrated in vacuo to afford Compound 50, (2S,4R)-l-(2-(2H-l,2,3-triazol-2- yl)acetyl)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2- carboxamide (171 mg, 89% yield), as a white solid. Major isomer: 1H-NMR (400MHz, DMSO-D6): ? 9.97 (s, IH), 7.80 (s, 2H), 7.58-7.51 (m, 2H), 7.34-7.07 (m, 6H), 7.04-6.90 (m, 4H), 5.48 (q, 2H), 4.53-4.46 (m, IH), 3.85-3.76 (m, IH), 2.77-2.61 (m, 3H), 2.03-1.86 (m, 2H). MS (EI) for C28H25F2N5O3, found 517.9 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4320-91-6, its application will become more common.

Reference:
Patent; EXELIXIS, INC.; IBRAHIM, Mohamed, Abdulkader; JEONG, Joon, Won; JOHNSON, Henry William, Beecroft; KEARNEY, Patrick; LEAHY, James, W.; LEWIS, Gary, L.; NOGUCHI, Robin, Tammie; NUSS, John, M.; WO2010/45580; (2010); A1;,
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. 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Phenyl-1,2,4-triazolidine-3,5-dione

General procedure: A mixture of dimedone (1 mmol), aldehyde or isatin (1 mmol) and 4-phenylurazole (1 mmol), and catalyst (0.01 g, 5 mol%) in water (5 mL) was refluxed. After completion of the reaction that was monitored by TLC (EtOAc:n-hexane, 1:3), the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with water and cooled with ethanol to afford the pure product.

According to the analysis of related databases, 15988-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Seyyedhamzeh, Mozhdeh; Shaabani, Shabnam; Hamidzad Sangachin, Mona; Shaabani, Ahmad; Research on Chemical Intermediates; vol. 42; 4; (2016); p. 2845 – 2855;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-70-2,Some common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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.

3A: (2S,4R)-5-(3′-Fluorobiphenyl-4-O-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid 1,2,3-Triazole-4-carboxylic acid (27.3 mg, 241 mumol) was combined with EDC (42.7 muL, 241 mumol), 4-methylmorpholine (1 eq.) and HOBt (32.6 mg, 241 mumol) in DMF (0.2 mL). The resulting mixture was stirred for 5 minutes at room temperature. A solution (2S,4R)-4-amino-5-(3′-fluorobiphenyl-4-yl)-2-hydroxymethyl-2-methylpentanoic acid (80 mg, 240 mumol) and 4-methylmorpholine (53.1 muL, 483 mumol) in DMF (0.3 mL) was added, and the resulting mixture was stirred for 15 minutes. The reaction was quenched with ACOH and the product was purified by preparative HPLC and lyophilized to yield the title compound (30 mg). MS m/z [M+H]+ calc’d for C22H23FN4O4, 427.17. found 427.2.

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-4-carboxylic acid, its application will become more common.

Reference:
Patent; Fleury, Melissa; Hughes, Adam D.; US2014/45906; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 27808-16-8, 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. 27808-16-8 name is 4-Methyl-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.

A solution of 4-methyl-iH-i,2,3-triazole (500 mg,6.02 mmol), 2,3-dichloro-5-nitropyridine (1277.42 mg, 6.62 mmol), K2C03 (2491.22 mg, 18.05 mmol) in CH3CN (5 mE) was stirred at it for 12 h. The mixture was concentrated under reduced pressure, the crude product was purified by colunm chromatography over silica gel (petroleum ether ethyl acetate from 20:1 to 1:1). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford i25a (1.1 g, 76.3%) as a yellow solid. ECMS (ESI) mlz M+i: 239.7. Zn (1491.96 mg, 22.95 mmol) was added to a solution of mixture of 3-chloro-2-(4-methyl-2H-i,2,3-tri- azol-2-yl)-5-nitropyridine and 3-chloro-2-(4-methyl-i H-i, 2,3-triazol-i-yl)-5-nitropyridine, i25a (1.1 g, 2.30 mmol) in aqNH4C1 (30 mE) and H20 (30 mE). The mixture was stirred at it for 16 h. To the suspension was added aq NaHCO3 to adjust to pH 9-10, and the mixture was filtered through a pad of diatomaceous earth. The filter cake was washed with CH2C12 (100 mEx3). The combined filtrates were washed with brine (200 mE), dried over MgSO4 and concentrated under reduced pressure to afford mixture of 5-chloro-6-(4-methyl-2H- 1 ,2,3-triazol-2-yl)pyridin-3-amine and 5-chloro-6-(4-methyl-i H-i ,2,3-triazol- 1 -yl)pyriF din-3-amine, 125b (1 g) as a brown solid, used directly for the next step. LCMS (ESI) mlz M+H: 209.7

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-1H-1,2,3-triazole, and friends who are interested can also refer to it.

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

Synthetic Route of 60166-43-0, 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. 60166-43-0 name is 1,4-Dimethyl-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.

In a pressure vessel equipped with a magnetic stirring bar, was added (Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

118863-62-0, name is 3-(4-Bromophenyl)-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. HPLC of Formula: C8H6BrN3

To a solution of 1-iodo-4-(trifluoromethoxy)benzene (15.0 g, 52.0 mmol) in dimethylformamide (90 mL) and water (10 mL) was added 3-(4-bromophenyl)-1H-1,2,4-triazole (C51) (11.0 g, 49.0 mmol), cesium carbonate (34.0 g, 104 mmol), copper(I) iodide (2.80 g, 14.7 mmol), and 8-hydroxyquinoline (2.20 g, 15.0 mmol), and the solution was heated at 140 C. for 8 hours. The cooled solution was decanted from a layer of solid, diluted with a ammonium hydroxide (1N, 100 mL) solution, and extracted with of diethyl ether (2*100 mL). The combined organic layer was dried and concentrated, and the brown solid was eluted through a short silica gel column using 20% ethyl acetate/hexanes as eluent to give the title compound as a light tan solid (9.50 g, 50%): mp 111-113 C., 1H NMR (400 MHz, CDCl3) delta 8.56 (s, 1H), 8.07 (d, J=8.6 Hz, 2H), 7.79 (d, J=8.8 Hz, 2H), 7.62 (d, J=8.6 Hz, 2H), 7.39 (d, J=8.8 Hz, 2H); ESIMS m/z 384 ([M+H]+).

The synthetic route of 118863-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; Fischer, Lindsey G.; Baum, Erich W.; Crouse, Gary D.; DeAmicis, Carl; Lorsbach, Beth; Petkus, Jeff; Sparks, Thomas C.; Whiteker, Gregory T.; US2014/274688; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics