Triazoles

Reference of 41253-21-8, A common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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.

(ii) Preparation of crude anastrozole of formula-I; Into a 10L, three-necked RB flask was charged l.4kg of above crude compound of formula-V and 7L of anhydrous DMF. The reaction mass was stirred for 30min and added 0.65kg of solid sodium triazole (prepared by reaction of molar quantities of 1,2,4- IH-triazole and sodium hydroxide in isopropanol at reflux temperature and isolated by filtering of the reaction mass at room temperature) in lots keeping the temperature below 25 C. The reaction mass was maintained under stirring at this temperature for 4hr. HPLC of the reaction mass indicated the absence of starting material. The reaction mass was transferred into a 50L flask containing 21L of water and stirred for 30min. Reaction mass was extracted with toluene (2 x 3L and 1 x 1L). Toluene layers were combined and . washed with water (2 x 2L). Toluene was distilled of from the filtrate under vaccum to get 1.2kg of crude anastrozole.; Example 3; Preparation of pure anastrozole of the formula-I; (i) Preparation of crude anastrozole; Into a 1L, three-necked RB flask was charged 45g of anhydrous sodium triazole and 250ml of dry DMF under nitrogen atmosphere. The reaction mass was cooled to 25 C. Bromo compound of formula-V (100g, prepared according to the process given in EP 0296749, example 1) was added to the reaction mass over a period of 2hr. The reaction mass was maintained at this temperature until the completion of reaction. The reaction mass was transferred into 3L flask containing 1.6L of water and stirred for 30min. Reaction mass was extracted with toluene (2 x 300ml and 1 x 100ml). Toluene layers were combined and washed with water (2 x 200ml). Toluene layer was treated with activated carbon (5g) and filtered. Toluene was distilled of from the filtrate under vaccum to get 95g of crude anastrozole.; Example 4; Preparation of pure anastrozole of the formula-I; (i) Preparation of crude anastrozole; Into a 1L, three-necked RB flask was charged 60g of sodium triazole monohydrate and 400ml of dry DMF under nitrogen atmosphere. The reaction mass was cooled to 25 C. Bromo compound of formula-V (100g, prepared according to the process given in EP 0296749, example 1) was added to the reaction mass over a period of 2hr. The reaction mass was maintained at this temperature until the completion of reaction. The reaction mass was transferred into 3L flask containing 1.6L of water and stirred for 30min. Reaction mass was extracted with toluene (2 x 300ml and 1 x 100ml). Toluene layers were combined and washed with water (2 x 200ml). Toluene layer was treated with activated carbon (5g) and filtered. Toluene was distilled of from the filtrate under vaccum to get 96g of crude anastrozole.

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

Reference:
Patent; NATCO PHARMA LIMITED; PULLA REDDY, Muddasani; VENKAIAH CHOWDARY, Nannapaneni; WO2005/105762; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7411-23-6, A common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, 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.

3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) and salicylic alcohol2c (447 mg, 2.9 mmol) were refluxed for 2 h in DMF (10 mL). Aftercompletion of the reaction, the mixture was cooled and poured intoH2O (30 mL). The precipitate formed was collected by filtration,washed with H2O, dried, and recrystallized from EtOH; yield: 585 mg(60%); colorless crystals; mp 149-150 C.IR (KBr): 3500-3000 (O-H), 1612, 1593, 1553, 1520, 1485, 1468,1433, 1364, 1290, 1267, 1231, 1184, 1069, 1005, 916, 837, 777, 760,721, 704 cm-1.1H NMR (400 MHz, DMSO-d6): delta = 9.09 (s, 1 H, OH), 6.91 (dd, J = 8.2,1.2 Hz, 1 H, Ar), 6.73 (t, J = 7.9 Hz, 1 H, Ar), 6.57 (d, J = 7.6 Hz, 1 H, Ar),5.26 (s, 2 H, CH2), 3.75 (s, 6 H, 2 ¡Á CH3O).1H NMR (400 MHz, CD3CN): delta = 6.91 (dd, J = 8.0, 1.4 Hz, 1 H, Ar), 6.89(br s, 1 H, OH), 6.79 (t, J = 8.0 Hz, 1 H, Ar), 6.66 (dd, J = 7.8, 1.4 Hz, 1 H,Ar), 5.27 (s, 2 H, CH2), 3.82 (s, 6 H, 2 ¡Á CH3O).13C NMR (100 MHz, DMSO-d6): delta = 148.0 (C), 144.8 (C), 139.6 (C),131.7 (C), 121.5 (C, CH), 119.5 (CH), 112.4 (CH), 56.4 (2 ¡Á CH3), 49.2(CH2).13C NMR (100 MHz, CD3CN): delta = 147.2 (C), 144.2 (C), 139.4 (C), 130.5(C), 121.4 (CH), 120.3 (C), 119.7 (CH), 111.7 (CH), 55.9 (2 ¡Á CH3), 48.7(CH2).Anal. Calcd for C10H9Br2N3O2: C, 33.09; H, 2.50; N, 11.58. Found: C,32.95; H, 2.41; N, 11.45.

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; 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 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.

A solution of 1-methyl-1H-1,2,3-triazole (0.28 g, 3.37 mmol) in dry THF (3 mL) was cooled in a -78 C. bath and n-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-N-methoxy-N-methylpiperidine-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 NH4Cl. The aqueous mixture was extracted with EtOAc (2*). The combined EtOAc extracts were dried over Na2SO4, filtered, concentrated to dryness and chromatographed (EtOAc/DCM) to provide the title compound.

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

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

Some common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-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. name: 3-Methyl-1H-1,2,4-triazole

To a stiffing solution of 4-fluorobenzaldehyde (5.0 g, 40.32 mmol) in DMF (50 mL), were added K2CO3 (3.34 g, 40.32 mmol) and 3-methyl-1,2,4-trizole (3.34 g, 40.32 mmol) and the resultant reaction mixture was stirred at RT for 4 h. After completion of the reaction (TLC), the reaction mixture was diluted with water and extracted with EtOAc (3*). The combined EtOAc layer was washed with water and brine then dried over Na2SO4 and concentrated under reduced pressure to afforded the title compound as a white solid (4.1 g, 60%): mp 125-128 C.; 1H NMR (400 MHz, CDCl3) delta 10.05 (s, 1H), 8.76 (s, 1H), 8.02 (d, 2H), 7.85 (d, 2H), 2.50 (s, 3H); ESIMS m/z 188.04 ([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 7170-01-6, its application will become more common.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171312; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

138624-97-2, name is 1-Benzyl-1H-1,2,4-triazole-3-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. Recommanded Product: 138624-97-2

To a screw cap vial 6-amino-4-methyl-2-(trifluoromethyl)-7,8-dihydro-4H-pyrazolo[1,5-a][1,3]diazepin-5(6H)-one (74mg, 0.298 mmol), l-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (158 mg, 0.417 mmol), 1-benzyl-1H-1,2,4-triazole-3-carboxylic acid (76mg, 0.358 mmol) was added and dissolved in N,N-dimethylformamide (5 mL). To the reaction mixture was added trimethyl amine (0.166 mL, 1.19 mmol), the vial was capped and stirred at RT for 16 h. The mixture was concentrated to dryness in vacuo and the residue was purified by RP-HPLC affording 1-benzyl-N-(4-methyl-5-oxo-2-(trifluoromethyl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,3]diazepin-6-yl)-1H-1,2,4-triazole-3-carboxamide (77mg, 59% yield): 1H NMR (400 MHz, DMSO-d6) delta 8.82 (s, 1H), 8.63 (d, J = 7.6 Hz, 1H), 7.49 – 7.19 (m, 5H), 6.93 (s, 1H), 5.49 (s, 2H), 4.51 – 4.42 (m, 1H), 4.39 – 4.27 (m, 2H), 3.27 (s, 3H), 2.72 – 2.59 (m, 1H), 2.48 – 2.42 (m, 1H). LC-MS RT = 4.34 min, m/z = 434.1 (M+H) +. LCMS (2 to 98% acetonitrile in water + 0.1% formic acid over 10 mins) retention time 4.34 min, ESI+ found [M+H] = 434.1.

The synthetic route of 138624-97-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, belongs to Triazoles compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 135242-93-2, HPLC of Formula: C4H7N3O

To a mixture of 176 (1-methyl-1H-1,2,4-triazol-3-yl)methanol (400 mg, 3.54 mmol) and 177 iodobenzene diacetate (1.25 g, 3.89 mmol) in 68 dichloromethane (10 mL) was added 178 TEMPO ((2,2,6,6-tetramethylpiperidin-1-yl)oxyl) (56 mg, 354 mumol). The mixture was stirred at 15-20 C. for 2 h. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=1:2) to give 179 1-methyl-1H-1,2,4-triazole-3-carbaldehyde (300 mg, 2.70 mmol, 76% yield). 1H NMR (chloroform-d 400 MHz) delta 10.01 (s, 1H), 8.19 (s, 1H), 4.06 (s, 3H

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; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Kehler, Jan; Rasmussen, Lars Kyhn; Clementson, Carl Martin Sebastian; Marigo, Mauro; (154 pag.)US2019/194189; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 4928-87-4, These common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, 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.

10.9 mg (0.077 mmol) of 1,2,4-triazole-3-carboxylic acid was dissolved in 5 ml of dichloromethane and 45.2 mg(0.119 mmol) of 2- (7-azobenzotriazole-Nu, Nu, N ‘, N’-tetramethyluronium hexafluorophosphate under ice bath was added 21.9 mg(0.216 mmol) of triethylamine,Stirring for 30min,30 mg of intermediate 121 (0.054 mmol) was added,Stir overnight at room temperature. TLC checkMeasurement,After the reaction,Add lml of saturated sodium bicarbonate solution,Stirring for 20min,Dispensing,The aqueous phase was extracted with dichloromethane,mergeThe organic phase,dry,Steamed in crude.The crude product was purified by preparative silica gel plate (methanol: dichloromethane = 1: 10)The target compound was 9 mg in 21%

Statistics shows that 1,2,4-Triazole-3-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 4928-87-4.

Reference:
Patent; Beijing Foreland Pharma Co., Ltd; Zhang, Xingmin; Wang, Ensi; Niu, Shengxiu; Guo, Jing; Dai, Zhuolin; Zheng, Nan; Ji, Qi; Li, Qinyan; Liang, Tie; (109 pag.)CN104411706; (2016); B;,
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. 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Safety of 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one

Step 2I-8 2.34200 mg 5-Chloromethyl-2,4-dihydro-[1 ,2,4]triazol-3-one was placed in 25 mL of a 7N solution of ammonia in methanol at ambient temperature. The reaction was stirred overnight and then concentrated under reduced pressure. The product was used without further purification. Yield: 171 mg (100percent of theory)

The synthetic route of 252742-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; DAHMANN, Georg; FIEGEN, Dennis; HANDSCHUH, Sandra; KLICIC, Jasna; LINZ, Guenter; SCHAENZLE, Gerhard; SCHNAPP, Andreas; EAST, Stephen P.; MAZANETZ, Michael Philip; SCOTT, John; WALKER, Edward; WO2011/92128; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 6523-49-5, These common heterocyclic compound, 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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.

A mixture of N’-(3-Cyano-4′-hydroxy-3′-methoxy-biphenyl-4-yl)-N,N-dimethyl- formamidine (220mg) and triazolyl aniline (113mg) in acetic acid (2ml) was heated to 125 for 2h. The cooled mixture was diluted with water and filtered under suction overnight. The resulting solid was sonicated in acetone (20ml) with warming and filtered. The solid was dried to give the title compound as a yellow solid (28mg)..1H NMR (D6-DMSO) delta 3.86 (3H, s); 6.88 (IH, d); 7.28 (IH, d); 7.36 (IH, s); 7.82 (3H, m); 8.03 (2H, m); 8.15 (2H, m); 8.56 (IH, s); 8.69 (IH, s); 9.2 (2H, s); 9.98 (IH, s); LC- MS rt 2.14 m/z 411 ES+

Statistics shows that 4-(1,2,4-Triazol-1-yl)aniline is playing an increasingly important role. we look forward to future research findings about 6523-49-5.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); 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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., name: 3,5-Dibromo-1H-1,2,4-triazole

In a 250 mL round bottomed flask, 3,5-dibromo-1H-1,2,4-triazole (Int-1, 8.00 g, 35.3 mmol) was dissolved in DMF (80 mL) and the solution was cooled to 0-5 C (ice bath). Sodium hydride (60% dispersion in mineral oil, 1.69 g, 42.3 mmol) was added in portions and the resulting mixture was stirred for 45 min at 0-5 C and for 15 min at room temperature. After that, iodomethane (10.0 g, 4.41 mL, 70.5 mmol) was added dropwise at 0-5 C (ice bath). The resulting mixture was stirred for 18 h at room temperature. After that, it was concentrated in vacuo, the residue was diluted with ethyl acetate (200 mL) and water (200 mL), the aqueous phase was extracted with ethyl acetate (2 x 200 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo to yield the title compound as light yellow solid (8.15 g, 96%). 1H NMR (CDCl3, 300 MHz): delta 3.89 (3 H). MS (ES+) m/z 240.0, 242.0, 244.0 [M+H, 2 Br isotopes].

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics