Day: March 1, 2021

Electric Literature of 7170-01-6, A common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, molecular formula is C3H5N3, 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.

To a solution of 2-chloro-4-fluorobenzaldehyde (95 mmol, 15 g) and 3-methyl-lH-l,2,4-triazole (114 mmol, 9.4 g) in CH3CN (300 mL) was added K2C03 (142 mmol, 20 g) and stirred at 60 C. After 24 h, the reaction mixture was added water and extracted with EtOAc. The organic extracts washed with saturated aq. NaCl, dried over Na2S04, filtered and concentrated in vacuo. The crude was purified by column chromatography (heptane: EtOAc = 20:80-10:90) to give the title compound. MS (ESI) m/z = 222, 224 (M+H) 1H NMR (300 MHz, CDC13) delta (ppm): 10.45 (1H, s), 8.55 (1H, s), 8.06 (1H, d, J= 8.6 Hz), 7.87 (1H, d, J= 2.1 Hz), 7.68 (1H, dd, J= 8.6, 2.1 Hz), 2.51 (3H, s).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SAKURADA, Isao; HIRABAYASHI, Tomokazu; MAEDA, Yoshitaka; NAGASUE, Hiroshi; MIZUNO, Takashi; XU, Jiayi; ZHANG, Ting; SMITH, Cameron; PARKER, Dann; WO2015/160634; (2015); A1;,
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. 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. category: Triazoles

[0856] 3H-1,2,3-triazole-4-carboxylic acid (3.4 mg, 30f.tmol) was combined with HATU (11 mg, 30 f.tmol) in DMF(0.3 mL) and stirred at room temperature for 10 minutes;DIPEA (1 eq.) was added and the mixture was stirred for 1minute. Compound2 (lOmg, 30 f.tmol) inDMF (0.5 mL)wascombined with DIPEA (5.2 f.LL, 30 f.tmol), then added to theactivated acid solution. The resulting solution was stirred atroom temperature for 30 minutes; LC/MS showed the mass ofthe desired product. The solvent was removed in vacuo andthe crude residue was purified by reverse phase chromatographyto yield Compound a (8.5 mg) as a TFA salt. MS rn/z[M+Ht calc’d for C27H31ClFN50 4 , 544.21; found 545.2.

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.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 584-13-4, name is 4H-1,2,4-Triazol-4-amine, 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 584-13-4, name: 4H-1,2,4-Triazol-4-amine

Compound (3) (4-(4H-1,2,4-Triazol-4-ylamino)benzonitrile) was synthesized by reacting Compound (1) with Compound (2) in the presence of potassium tert-butoxide in DMSO according to the method described in Non-patent Literature 3 (Okada, M.; Yoden, T.; Kawaminami, E.; Shimada, Y.; Kudoh, M.; Isomura, Y.; Shikama, H.; Fujikura, T., Chem. Pharm. Bull. 1996, 44, 1871-1879).

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, 4H-1,2,4-Triazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Riken; EP2450354; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 10570-40-8, The chemical industry reduces the impact on the environment during synthesis 10570-40-8, name is 4-Methyl-4H-1,2,4-triazole, I believe this compound will play a more active role in future production and life.

General procedure: A solution of 1,4-dichloro-2-butyne (1.23 g, 10 mmol) and the respective N-alkylazole (20 mmol) in MeCN (15 mL) was stirred at 80 C for 24 h. The precipitate wascollected by filtration, washed with MeCN, and dried under reduced pressure.

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, 4-Methyl-4H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Haslinger, Simone; Laus, Gerhard; Oberparleiter, Stefan; Wurst, Klaus; Kahlenberg, Volker; Nerdinger, Sven; Schreiner, Erwin; Schottenberger, Herwig; Heterocycles; vol. 95; 2; (2017); p. 1148 – 1158;,
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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, A new synthetic method of this compound is introduced below., Safety of 2-(2H-1,2,3-Triazol-2-yl)benzoic acid

General procedure: Et3N (0.45 mL, 3.3 mmol) was added to a solution of 2-(1H-pyrazol-4-yl)ethanamine dihydrochloride (0.30 g, 1.6 mmol) in DMF (5 mL) at room temperature, followed by stirring. 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (0.36 g, 1.8 mmol), HOBt.H2O (0.37 g, 2.4 mmol), and EDC.HCl (0.47 g, 2.4 mmol) were added to the reaction solution, followed by stirring at room temperature for 3 hours. An aqueous NaHCO3 solution was added to the reaction mixture, followed by extraction with EtOAc. The organic layer was washed with water and brine and was dried with Na2SO4. The desiccant was then removed by filtration, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (KP-NH: 28 g, CHCl3/MeOH=100/0 to 97/3) to give the titled compound (0.43 g, colorless and amorphous). MS (ESI pos.) m/z: 297 [M+H]+

The synthetic route of 1001401-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Suzuki, Ryo; Futamura, Aya; Abe, Masahito; Kashiwa, Shuhei; Hattori, Nobutaka; Nozawa, Dai; Ohta, Hiroshi; Araki, Yuko; US2014/81025; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 162848-16-0,Some common heterocyclic compound, 162848-16-0, name is 4-[1,2,4]Triazol-1-yl-benzoic acid, molecular formula is C9H7N3O2, 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 5: Synthesis of 4-[l,2,4]triazol-l-yl-benzoic acid 3-(2-methyl-l,2,3,4- tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide (Cpd 178, Table 1); Dissolve 4-[l,2,4]triazol-l-yl-benzoic acid (29 mg, 0.15 mmol) and CDI (Nu,Nu’- carbonyldiimidazole) (25 mg, 0.15 mmol) in DMF (2 mL) and stir the mixture for 1 h. To this add 3-aminomethyl-N-(2-methyl-l,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamide dihydrochloride (50 mg, 0.14 mmol) and triethylamine (0.095 mL, 0.68 mmol) and stir the mixture overnight. Dilute the mixture with water (1 mL) and trifluoroacetic acid (0.2 mL) and purify by prep-HPLC (5 -70 , CH3CN/H20) to give the desired product 4- [l,2,4]triazol-l-yl-benzoic acid 3-(2-methyl-l,2,3,4-tetrahydro-isoquinolin-7- ylcarbamoyl)-benzylamide (51 mg, 0.086 mmol). MS, electrospray 467.4 (M+H), rt 1.05 min.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KOWALSKI, Jennifer A.; LI, Xiang; MARSHALL, Daniel Richard; SCHLYER, Sabine; SIBLEY, Robert; SMITH-KEENAN, Lana Louise; SOLEYMANZADEH, Fariba; SORCEK, Ronald John; YOUNG, Erick Richard Roush; ZHANG, Yunlong; WO2012/6203; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

In a 250 mL round bottomed flask sodium hydride (60% dispersion in mineral oil) (264 mg, 6.61 mmol) was added to a colorless solution of 3,5-dibromo-1H-1,2,4-triazole (Int-1, 1 g, 4.41 mmol) in DMF (22 ml). The resulting suspension was stirred at room temp during 30 min and 1-bromo-2-methoxypropane (809 mg, 5.29 mmol) was added and the reaction was stirred at 40C over night. The reaction mixture was poured into 50 mL H2O and extracted with EtOAc (3 x 50 mL). The organic layers were washed with sat NaCl (3 x 50 mL), dried over MgS04 and concentrated in vacuo. The title compound was isolated as a red liquid (383 mg, 14.5 % yield). MS (ES+) m/z 299.9 [(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-1H-1,2,4-triazole, its application will become more common.

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

Some common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, 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. Application In Synthesis of 3,5-Diamino-1,2,4-triazole

3′-chloroacetophenone was used in place of 2-acetylthiophene in Reference Example 001 and heated to reflux in xylene in the presence of N,N-dimethylformamide diethyl acetal as in Reference Example 001, and 3-dimethylamino-1-(3-chlorophenyl)propenone (quantitative) was obtained, which was subsequently reacted with 3,5-diamino-1,2,4-triazole in toluene in the presence of 10-camphor sulfonic acid and the title compound was obtained (yield 44percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1455-77-2, its application will become more common.

Reference:
Patent; NIPPON KAYAKU KABUSHIKI KAISHA; EP1674454; (2006); 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 7170-01-6 as follows. Product Details of 7170-01-6

Procedure: A 500 mL round bottom flask was loaded with 4-methoxy-7-chloro-6-azaindole precursor 2e (9.1 g, 50 mmol; dried in vacuo), potassium carbonate (13.8 g, 100 mmol, 2 eq.), copper powder (6.35 g, 100 mmol, 2 eq.), and 3-methyl-1,2,4-triazole (83 g, 1.0 mol, 20 eq.). The solid mixture was heated to melt at 170-175 C. (external oil bath temperature) under gentle stream of anhydrous nitrogen for 12 h, by which time HPLC analysis indicates the amount of the peak for the starting material becomes 5-30% and the desired product peak becomes about 45% with isomeric by-product peak becomes 15%. As the reaction mixture cools, MeOH (150 mL) was added slowly to the stirred warm mixture. Upon cooling, the insoluble material (copper powder) was filtered through a Celite pad, and rinsed with methanol. The filtrate was concentrated in vacuo to a thick paste which was diluted with water (1 L) and extracted with EtOAc (3¡Á150 mL). The EtOAc extracts were dried (MgSO4), filtered and concentrated to obtain about 8 g of crude residue which was crystallized by dissolving in hot CH3CN (50 mL), followed by diluting with water (100 mL) and cooling at 0 C. to collect 1.45 g (12.7%) of the title compound as white solid. The filtrate was purified by C-18 reverse phase silica gel (YMC ODS-A 75 mum) eluted with 15-30% CH3CN/H2O. Appropriate fractions were combined and the aqueous solution after removing CH3CN by rotary evaporator was lyophilized to give additional 1.15 g of the title compound 3-81. The crude aqueous layer was further extracted with EtOAc several times. The ethyl acetate extracts were dried (MgSO4), filtered, concentrated, and crystallized from MeOH to give additional 200 mg of the title compound 3-81. The total yield: 2.8 g (12.2 mmol, Y. 24.5%); MS m/z 230 (MH), HRMS (ESI) m/z calcd for C11H12N5O (M+H), 230.1042, found 230.1038 (Delta-1.7 ppm); 1H NMR (CDCl3) delta ppm 2.54 (3H, s, CH3), 4.05 (3H, s, OCH3), 6.73 (1H, s, H-3), 7.40 (1H, s, H-2), 7.56 (1H, s, H-5), 9.15 (1H, s, triazole-H-5); 13C NMR (CDCl3, 125.7 MHz) delta ppm 14.2 (triazole-Me), 56.3 (OMe), 100.5 (C-3), 116.9 (C-5), 123.5, 127.2, 127.5 (C-2), 129.5 (C-7), 141.2 (C-5′), 149.5 (C-4), 161.8 (C-3′); Anal. Calcd for C11H11N5O:C 57.63, H 4.83, N 30.55, found C 57.37, H 4.64, N 30.68. [1514] The structure was confirmed by a single X-ray crystallographic analysis using crystals obtained from C-18 column fractions. A portion of C-18 column fractions containing a mixture of the desired 3-methyl-1,2,4-triazolyl analog 3-81 and isomeric 5-methy-1,2,4-triazolyl analog 4-81 was further purified by C-18 reverse phase column eluting with 8-10% CH3CN/H2O. Appropriate fractions were extracted with CH2Cl2, and slow evaporation of the solvent gave crystalline material of the isomeric 7-(5-methy-1,1,2,4-triazolyl)-4-methoxy-6-azaindole (4-81): MS m/z 230 (MH), 1H NMR (CDCl3) delta ppm 3.05 (3H, s, CH3), 4.07 (3H, s, OCH3), 6.74 (1H, q, J=2.4, H-2), 7.37 (1H, t, J=2.4, H-3), 7.65 (1H, s, H-5), 8.07 (1H, s, triazole-H-3). The structure was confirmed by a single X-ray crystallographic analysis.

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; Kadow, John F.; Yin, Zhiwei; Xue, Qiufen May; Regueiro-Ren, Alicia; Matiskella, John D.; Ueda, Yasutsugu; US2004/110785; (2004); 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 41253-21-8 as follows. name: Sodium 1,2,4-triazol-1-ide

Triazole sodium salt (6.54 mmol) was dissolved in NMP 4 mL and the mixture was heated to 115 C. (internal temperature). 2-(4-Fluorobenzyl)-8,8-dimethyl-7,9-dioxa-spiro[4,5] decan-1-one (compound (XVI-1): Ym=4-F) 1.27 g dissolved in NMP 3 mL was added thereto. After the internal temperature reached 116 C., sodium t-butoxide (2.61 mmol) and TMSOB (5.87 mmol) were added in portions over 2.3 hours to carry out the reaction. After all reagents were added, the mixture was agitated additionally for 25 minutes. The reaction solution was cooled to room temperature; saturated aqueous sodium chloride solution was added thereto; and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography, to give the title compound (XV-1) as an isomer mixture.Yield: 66.7%

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; KUREHA CORPORATION; Araki, Nobuyuki; Miyake, Taiji; Imai, Eiyu; Obata, Emiko; US2014/179517; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics