Day: March 16, 2021

Synthetic Route of 7411-23-6, These common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-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.

General procedure: 3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) or 3-chloro-1,2,4-triazole (300 mg, 2.9 mmol), o-quinone methide precursor 2 (2.9mmol), and K2CO3 (1.2 g, 8.7 mmol) were refluxed for 4 h in DMF (10mL). After completion of the reaction, the mixture was cooled, andpoured into H2O (30 mL). The precipitate formed was collected by filtration,washed with H2O, dried, and recrystallized.

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

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

Electric Literature of 956317-36-5, 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. 956317-36-5 name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, 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.

Step 2) Synthesis of 5-methyl-2- (2H-1, 2, 3-triazol-2-yl) benzoyl chlorideTo a solution of 5-methyl-2- (2H-1, 2, 3-triazol-2-yl) benzoic acid (2.03 g, 10 mmol) in anhydrous DCM (20 mL) were added sulfoxide chloride (15 mL, 206 mmol) and pyridine (0.15 mL, 2 mmol) slowly. The reaction was heated to reflux for 3 hours, and then cooled. The solvent was removed in vacuo to give a product, which was used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; ZHANG, Ji; (90 pag.)WO2017/88759; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-70-2, name is 1H-[1,2,3]Triazole-4-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. SDS of cas: 16681-70-2

lH-l,2,3-triazole-4-carboxylic acid (50.8 mg, 449 muiotaetaomicron) and HATU (171 mg, 449 muiotaetaomicron) were dissolved in DMF (3 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 (160 mg, 409 muiotaetaomicron) and DIPEA (214 mu^, 1.2 mmol) were added, and the mixture was stirred at room temperature for 15 minutes, at which time LCMS indicated the mass of the desired compound. The mixture was then concentrated in vacuo to yield Compound 1, which was used in the next step without purification.

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

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. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-(1,2,4-Triazol-1-yl)aniline

To a solution of formamidine from Step 3 (250mg, 0.73mM) in acetic acid (2ml) was added the 4-triazolylaniline (117mg, 0.73mM). The reaction was heated to 125C for2hrs. The mixture was cooled down and 15ml of 2N NaOH was added. The product crashed out and was isolated by filtration. The solid was purified by column (SiOH) with DCM:EtOH:NH3 400-200:8:1 and isolated as a yellow solid (258mg, 75%).1H NMR (D6-DMSO) delta 10.06 (IH , broad s), 9.29 (IH, s), 8.81 (IH, s) 8.63 (IH, s), 8.25 (2H, m), 8.09 (IH, s), 8.05 (IH, s), 7.83 (4H, m), 7.70 (IH, d, J 10Hz), 7.39 (IH, t,J 10Hz), 4.21 (2H, t, J 7.5Hz), 2.68 (2H, t, J 7.5Hz), 2.24 (6H , s).LC-MS rt 1.99 m/z 470 ES+

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; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-36-8, The chemical industry reduces the impact on the environment during synthesis 288-36-8, name is 1H-1,2,3-Triazole, I believe this compound will play a more active role in future production and life.

To a mixture of the product from step 2 (7.9 g, 38 mmoi), Cs2CO3 (24.8 g,76 mmol) and Cui (2.88 g, 7,6 inmol) in DMF (200 mL) were added 21-{41,2,3ltriazole (5.24 g,76 rnrnoi) and N,Ndimethyi-cyciohexanei,2-diamine (0.9 g, 6.5 rnmoi) and the mixture was stirred at 110C overnight. The cooled mixture was adjusled to pHi2 with 1M sodium hydroxide and extracled with EtOAc (50 mL x 3). The aqueous layer was adjusted to pH 4 with I M FIC and extractedwith EtOAc (50 mLx4). The extracts was dried over Na2SO4, filtered, the filtrate concentrated in vacuo and the residue purified by chromatography on silica (Petroleum ether : EtOAc =10:1) to provide the title compound. LRMS m/z (M-f-1-1) 196.0 found, 196.0 required.

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, 1H-1,2,3-Triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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. Formula: C3H5N3

D) ethyl 6-methyl-5-(4-methyl-1H-1,2,3-triazol-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate A mixture of ethyl 5-chloro-6-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate (400 mg), 4-methyl-1H-1,2,3-triazole (153 mg), potassium carbonate (277 mg) and N,N-dimethylformamide (5 mL) was stirred at room temperature overnight. The reaction mixture was poured into water at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (106 mg). MS (API+): [M+H]+287.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27808-16-8, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kawasaki, Masanori; Mikami, Satoshi; Nakamura, Shinji; Negoro, Nobuyuki; Ikeda, Shuhei; Nomura, Izumi; Ashizawa, Tomoko; Imaeda, Toshihiro; Seto, Masaki; Sasaki, Shigekazu; Marui, Shogo; Taniguchi, Takahiko; (130 pag.)US2016/159808; (2016); 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. 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 22300-52-3

The 10.0g (44.1mmol) 4,5- dibromo -2H-1,2,3- triazole (commercially available) was dissolved in 90ml of tetrahydrofuran was added 6.1g (44.2mmol) of potassium carbonate, cooled to -10 , was added 7.5g (53mmol) of methyl iodide.In the 35 ~ 40 to react until the reaction is complete.50ml of water was added, the tetrahydrofuran was distilled off, 90ml and extracted with methyl tert-butyl ether, dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure, the residual solid was added methyl tert-butyl ether, 10ml, 70ml of n-hexane was added slowly, solid precipitation, the addition was completed, stirring at room temperature for 1 to 2 hours.Filtered to give pure 4,5-dibromo-1-methyl -1H-1,2,3- triazole 5.8g, 57% yield.

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 22300-52-3.

Reference:
Patent; The Haiya Chemical Co., Ltd.; Jiang, Yueheng; Que, Limin; Xu, Jun; Qin, Dongguang; Cai, Tong; (17 pag.)CN105585534; (2016); A;,
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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

MnCl2¡¤4H2O (0.198 g, 1.0 mmol) in 3.0 mL of aqueous solution wasslowly added into a flask containing H3dctrz (0.078 g, 0.5 mmol) andpbtrz (0.08 g, 0.5 mmol) in 10.0 mL of aqueous solution. The reactingsolution was kept stirring for 6.0 h. The precipitate was filtrated, andcolourless crystals were isolated from the filtrate within 6 weeks. Yield:0.164 g (52.2% based on Mn(II)). Elemental analysis (EA) for calcd. 1(C6H8N6O6Mn, 315.12): C 16.96, H 1.78, N 22.25; found: C 17.34H 1.94, N 21.22%. IR (cm-1, s = strong, m = medium, w = weak): 3361s,3122s, 1625s, 1476s, 1411s, 1368w, 1353w, 1296s, 1162w, 1012m,984w, 892w, 841m, 670 m.

The synthetic route of 4928-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yan, Juan-zhi; Lu, Li-ping; Zhu, Miao-li; Feng, Si-si; Journal of Solid State Chemistry; vol. 262; (2018); p. 351 – 359;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 23579-79-5,Some common heterocyclic compound, 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, molecular formula is C3H3Br2N3, 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) 1 -(5-Bromo-2-methyl-2H-[ 1 ,2,4]triazol-3-yl)-ethanol To a solution of 3,5-dibromo-l-methyl-lH-l,2,4-triazole (2.634 g, 10.9 mmol, Eq: 1.00) in tetrahydrofuran (184 ml) was added dropwise at -78 C under argon atmosphere n- butyllithium 1.6 M in hexanes (6.83 ml, 10.9 mmol, Eq: 1.00). The resulting mixture was stirred for 20 minutes at -75 C then a solution of acetaldehyde (1.2 g, 1.54 ml, 27.3 mmol, Eq: 2.5) in tetrahydrofuran (36.9 ml) was added slowly and stirring at -75 C was continued for further 1.5 hours. The mixture was quenched with sat. aq. NH4C1 solution and was warmed to 25 C. The mixture was diluted with ethyl acetate and washed 2 times with water. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated affording l-(5-bromo-2- methyl-2H-[l,2,4]triazol-3-yl)-ethanol (1.639 g, 72.7%) as a light yellow oil. MS: m/z= 206/209 (M+H+)

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-Dibromo-1-methyl-1H-1,2,4-triazole, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KUHN, Bernd; LERNER, Christian; RUDOLPH, Markus; SCHAFFHAUSER, Herve; WO2013/178572; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1533519-84-4,Some common heterocyclic compound, 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, molecular formula is C15H13N3S, 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 the compound of Formula (5) (30 g, 112.22 mmol) in N,N-dimethylformamide (94 mL) was charged sodium bicarbonate (18.39 g, 218.96 mmol) to provide a suspension. 1,2-Bis(chloroacetoxy)ethane (compound of Formula (4-A)) (11.77 g, 54.74 mmol) was then charged and the mixture stirred at room temperature for 72 hours. Following the completion of the reaction, the reaction mixture was poured into ice water (250 mL) over 10 minutes to form a slurry, which was warmed to room temperature and stirred for 1 hour. The product was then collected by filtration, washed with cold (0-5 C.) water (2*60 mL), and suction dried for 45 minutes to provide a damp cake. A new flask was charged with the damp cake along with dichloromethane (300 mL) and stirred at room temperature for 30 minutes to afford a clear, biphasic solution. The organic phase was removed and washed with water (2*120 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo at 30-35 C. The foamy solid was then dried in vacuo at room temperature for 24 hours to afford the compound of Formula (3-A) as a foamy light yellow solid (quantitative yield, HPLC purity=99.35 area %). 1H-NMR (CDCl3, 300 MHz) delta: 0.75-0.94 (4H, m), 1.10-1.22 (4H, m), 2.41 (2H, tt, J=5.64 Hz, 8.47 Hz), 4.08 (ABq, 4H, DeltadeltaAB=0.05, JAB=16.36 Hz), 4.34 (4H, s), 7.29-7.43 (6H, m), 7.57 (2H, apparent dt, J=1.23 Hz, 7.64 Hz), 7.66 (2H, apparent dt, J=1.23 Hz, 7.60 Hz), 8.28 (2H, s), 8.53 (2H, d, J=8.35 Hz).

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

Reference:
Patent; Apotex Inc.; Bodhuri, Prabhudas; Green, Melanie R. A.; Karadeolian, Avedis; Weeratunga, Gamini; Gorin, Boris; (33 pag.)US2018/258057; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics