Day: May 14, 2021

Reference of 7411-23-6, 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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

a. A solution of 1.72 g (43 mmol) of sodium hydroxide in 2 mL of water was added with stirring to a solution of 10.0 g (43 mmol) of triazole 1 in 100 mL of DMF, and 6.49 g (43 mmol) of isopentyl bromide was then added. The mixture was stirred for 13 h on a boiling water bath, cooled, and poured into 1 L of water. The yellow oily material was separated using a separatory funnel (bottom layer), additionally washed with water, and dried for 3 days in a vacuum desiccator over phosphoric anhydride. The product was used in further syntheses without additional purification. Yield 11.5 g (89 %).

The chemical industry reduces the impact on the environment during synthesis 3,5-Dibromo-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Tolstyakov; Russian Journal of Organic Chemistry; vol. 54; 10; (2018); p. 1537 – 1547; Zh. Org. Khim.; vol. 54; 10; (2018); p. 1525 – 1534,10;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4928-87-4,Some common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-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.

Example 8 1-(1-(1H-1,2,4-triazole-3-carbonyl)pyrrolidin-3-yl)-3-methyl-8-(6-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-2(3H)-one In an ice-water bath, 48.8 mg (0.43 mmol) of 1,2,4-triazole-3-carboxylic acid and 200.76 mg (0.528 mmol) of 2-(7-azabenzotriazole)-N,N,N’,N’-tetramethyluronium hexafluorophosphate were dissolved in 5 mL of dichloromethane, added with 97 mg (0.96 mmol) of triethylamine and stirred at 0 C for 30 minutes, then added with 100 mg (0.24 mmol) of Intermediate 145 and stirred at room temperature overnight. The reaction was monitored by TLC. After the reaction was completed, 10 mL of saturated sodium bicarbonate aqueous solution was added, stirred for 20 minutes, and separated into layers. The aqueous phase was extracted with dichloromethane, and the organic phases were combined, dried, and rotary evaporated to dryness to afford a crude product. The crude product was purified with preparative silica gel plate (dichloromethane/methanol = 10/1, V/V) to afford the target compound of Example 8 (40 mg), as a white solid. Yield: 32%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2,4-Triazole-3-carboxylic acid, its application will become more common.

Reference:
Patent; Beijing Forelandpharma Co. Ltd.; ZHANG, Xingmin; JI, Qi; WANG, Lei; GAO, Congmin; WANG, Ensi; DU, Zhenjian; GONG, Longlong; CHEN, Bo; (137 pag.)EP3072893; (2016); 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. 118863-62-0, name is 3-(4-Bromophenyl)-1H-[1,2,4]triazole, A new synthetic method of this compound is introduced below., Formula: C8H6BrN3

Example 243 (S)-2-((1-(4-(1H-1,2,4-Triazol-3-yl)phenyl)-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]inden-4-yl)oxy)propanamide 243 243 was prepared using commercially available 3-(4-bromophenyl)-1H-1,2,4-triazole and following procedures analogous to those of Example 242. LCMS (ESI): RT (min)=1.02, [M+H]+=419, method=F; 1H NMR (300 MHz, DMSO-d6) delta 12.28 (br, 1H), 8.53 (s, 1H), 8.20 (d, J=8.4 Hz, 2H), 7.82 (d, J=8.4 Hz, 2H), 7.55 (s, 1H), 7.25 (s, 1H), 6.94 (d, J=2.1 Hz, 1H), 6.62 (d, J=2.1 Hz, 1H), 4.67-4.60 (m, 1H), 4.44-4.40 (m, 2H), 4.27-4.24 (m, 2H), 2.20-2.00 (m, 2H), 1.80-1.55 (m, 2H), 1.45 (d, J=6.6 Hz, 3H).

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

Reference:
Patent; Genentech, Inc.; Braun, Marie-Gabrielle; Garland, Keira; Hanan, Emily; Purkey, Hans; Staben, Steven T.; Heald, Robert Andrew; Knight, Jamie; Macleod, Calum; Lu, Aijun; Wu, Guosheng; Yeap, Siew Kuen; (183 pag.)US2018/65983; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

[003 87] To a solution of (+/-)-cis-N1 -(2-chloro-7-methyl-7H-pyrrolo[2, 3 -d]pyrimidin-4-yl) cyclohexane-1,3-diamine (60 mg, 0.21 mmol) in a mixed solvent of tetrahydrofuran (4 mL) and dimethyl sulfoxide (1 mL) was added N,N-diisopropylethylamine (0.11 mL, 0.64 mmol) and 1H-1,2,3-triazole-4-carboxylic acid (48 mg, 0.43 mmol). The mixture was stirred at rt for 10 minitues, and then HATU (163 mg, 0.43 mmol) was added. The resulting mixture was stirred at rt for 3 h. To the reaction mixture was added water (10 mL), and the resulting mixture was extracted with ethyl acetate (10 mL x 3). The combined organic layers were washed with saturated brine (30 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dry and give the title compound as a colorless solid (83 mg, 100%).MS (ESI, pos.ion) m/z: 375.2 [M+H]+

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 3641-13-2, A common heterocyclic compound, 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, molecular formula is C3H4N4O2, 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: A mixture of benzil (0.01 mol), aldehydes (0.01 mol), 3-amino-1,2,4-triazole-5-carboxylic acid (0.01 mol), ammonium acetate (0.01 mol) and ceric ammonium nitrate (15 mol%) as a catalyst were refluxed in ethanol (15 mL) for about 3-4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was cooled to room temperature. The solid formed was filtered and dried. The crude products were recrystallized by ethanol.

The synthetic route of 3641-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nikalje, Anna Pratima G.; Ghodke, Mangesh S.; Kalam Khan, Firoz A.; Sangshetti, Jaiprakash N.; Chinese Chemical Letters; vol. 26; 1; (2015); p. 108 – 112;,
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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C2H2N3Na

10.0 g of the compound of formula (FF) as oil, as obtained according to ReferenceExample 1.1. e, were dissolved in 80 ml of DMSO under stirring. Then, 10 g of the sodium salt of 1,2,4-triazole were added at 25 to 30 C, and the resulting reaction mixture was stirred for 24 hours at 85 to 90 C. The mixture was then cooled to 25 to 30 C, and 25 ml of 5 % (w/v) aqueous solution of sodium hydroxide were added. The mixture was then stirred for 3 hours at 25 to 30 C. 100 ml of water were added, and the product was extracted into 150 ml of methyl tetrahydrofuran. The thus obtained organic layer was washed with a 10 % (w/v) aqueous solution of sodium chloride, and subsequently the solvents of the resulting separated organic layer were removed by distillation under reduced pressure to obtain the title compound of formula (GG) as a crude oil. The yield was 6.0 g, corresponding to a theoretical value of 86.0 %.

According to the analysis of related databases, 41253-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANDOZ AG; WILHELM, Thorsten; LANGNER, Martin; WO2012/172015; (2012); 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. 7343-34-2, name is 3,5-Dimethyl-4H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3,5-Dimethyl-4H-1,2,4-triazole

Step 2: Benzyl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-oxobutanoate To a stirring solution of 3,5-dimethyl-1-H-[1,2,4]-triazole (0.502 g, 5.16 mmol) in THF (36.9 ml) was added NaH (0.199 g, 4.98 mmol). After stirring at RT for 10 mins 2-bromo-3-oxo-butyric acid benzyl ester (step 1) (1.0 g, 3.69 mmol) was added. The mixture was stirred at 40° C. for 30 mins and then allowed to cool to RT. The mixture was absorbed onto silica and purification by chromatography on silica eluting with 0-10percent DCM/MeOH afforded the title compound as an orange oil ; LC-MS Rt 1.95 mins; MS m/z 288.3 [M+H]+; Method LowpH_v001.

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 7343-34-2.

Reference:
Patent; Devereux, Nicholas James; McKenna, Jeffrey; US2011/190360; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, 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. 16681-70-2 name is 1H-[1,2,3]Triazole-4-carboxylic 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.

1,2,3-Triazole-4-carboxylic acid (45.2 mg, 400 mumol), DIPEA (209 muL, 1.2 mmol) and HCTU (165 mg, 400 mumol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 1-cyclohexyloxycarbonyloxy-ethyl ester (193 mg, 400 mumol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The products were purified and separated by preparative HPLC, then lyophilized to yield to yield compound ZC (20 mg; purity 95%), MS m/z [M+H]+ calc’d for C31H38N4O2, 579.27. found 579.6, and compound ZD (15 mg; purity 95%), MS m/z [M+H]+ calc’d for C31H38N4O2, 579.27. found 579.6.

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

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); A1;,
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 138624-97-2 as follows. category: Triazoles

A mixture of 7-amino-i ,5-dimethyl- 8 ,9-dthydro-7H-pyrido [3,2-b] azepine-2,6-dione(20 mg, 0.09 mmol), i-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (26 mg,0.14 mmol), 1 -hydroxybenzotriazole (18.3 mg, 0.14 mmol) and 1 -benzyl- 1 ,2,4-triazole-3-carboxylic acid (22 mg, 0.11 mmol) in N,N-dimethylformamide (1 mL) was stuffed at 25 Cfor 12 h. The mixture was concentrated under reduced pressure. The residue was purified byRP-HPLC (acetonitrile 20-50%/0.05% ammonium hydroxide in water) to afford the racemicmaterial (30 mg), which was separated by chiral SFC to give arbitrarily assigned:1 -benzyl-N- [(7R)- 1 ,5-dimethyl-2,6-dioxo- 8 ,9-dihydro-7H-pyrido [3,2-b] azepin-7-yl] – i,2,4-triazole-3-carboxamide (Peak 1, retention time 2.38 mm) (8.1 mg, 25%) as white solids.?H NMR (400 MHz, CD3OD) oe 8.56 (s, 1H), 7.58 (d, J = 10.0 Hz, 1H), 7.36 – 7.34 (m, 5H),6.57 (d, J = 9.2 Hz, 1H), 5.47 (s, 2H), 4.67 – 4.62 (m, 1H), 3.68 (s, 3H), 3.29 (s, 3H), 3.06 -3.05 (m, 1H), 2.88 – 2.84 (m, 1H), 2.75 – 2.72 (m, 1H), 2.27 – 2.22 (m, 1H). LCMS RT =0.695 mm, mlz = 407.1 [M + H]. LCMS (5 to 95% acetonitrile in water + 0.03%trifluoacetic acid over 1.5 mins) retention time 0.695 mi ESI+ found [M+H] =407.1.1 -benzyl-N-[(7S)- 1 ,5-dimethyl-2,6-dioxo-8,9-dihydro-7H-pyrido[3,2-b] azepin-7-yl] -i,2,4-triazole-3-carboxamide (Peak 2, retention time 3.639 mm) (5.3 mg, 17%) as white solids. ?H NMR (400 MHz, CD3OD) oe 8.56 (s, 1H), 7.58 (d, J = 9.6 Hz, 1H), 7.37 – 7.33 (m, 5H), 6.57 (d, J = 10.0 Hz, 1H), 5.47 (s, 2H), 4.67 – 4.62 (m, 1H), 3.68 (s, 3H), 3.29 (s, 3H),3.10 – 3.05 (m, 1H), 2.88 – 2.86 (m, 1H), 2.75 – 2.72 (m, 1H), 2.27 – 2.22 (m, 1H). LCMS RT = 1.202 mi mlz = 407.2 [M + H]. LCMS (10 to 80% acetonitrile in water + 0.05%ammonium hydroxide over 3 mins) retention time 1.202 mi ESI+ found [M+H] = 407.2. SFC condition: Column: Chiralpak AD-3 100×4.6mm I.D., 3um Mobile phase: A:C02 B: methanol (0.05% DEA) Gradient: from 5% to 40% of B in 5mm and hold 40% for 2.5 mm, then 5% of B for 2.5 mm Flow rate: 2.8mL/min Column temp.: 40 C.

According to the analysis of related databases, 138624-97-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; (105 pag.)WO2018/73193; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-65-5, 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. 16681-65-5 name is 1-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 1-methyl-1H-1,2,3-triazole (0.954 g, 11.4 mmol) (PCT Int. Appl., 2008098104; also commercially available from Matrix Scientific) in THF (22 mL) was stirred at -70 C. under argon while n-BuLi (2.56 M in hexanes; 4.29 mL, 11.0 mmol) was added dropwise over 5 min. After stirring for another 5 min, a solution of ethyl methoxy(methyl)carbamate (0.665 g, 4.99 mmol) (commercially available from Aldrich) in THF (3 mL) was added dropwise over 5 min. After stirring at -70 C. for an additional 5 min, the cold bath was removed and the light slurry was allowed to warm to room temperature with stirring for 1 hour 20 min. The reaction was then quenched at room temperature with 5 M NH4Cl (3 mL) and the aqueous layer was extracted with THF (1×6 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. A portion of the residue was crystallized from 30 mL toluene to provide, after washing the filter cake with ether (1×3 mL) and heptane (1×3 mL), the title compound as blunt needles.

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

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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics