Month: February 2021

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. COA of Formula: C3H3N3O2

General procedure: General Procedure (GP-Al) for carboxamide formation: A mixture of amine I (1 equiv) , desired carboxylic acid (1 equiv) , triethylamine (Et3N) (3 equiv) , and 2- (lfl-benzotriazole-l-yl) -1 , 1 , 3 , 3- tetramethyluronium hexafluoro-phosphate (HBTU) (1.5 equiv) in DMF (0.25 M) was stirred at room temperature until the reaction was complete by TLC or LC-MS. The mixture was diluted with 0 and extracted with EtOAc. The combined organic extracts were washed with H2O , brine, dried over Na2S0< , filtered, and concentrated under reduced pressure. The resulting residue was purified by either normal phase silica gel column chromatography (typical eluents included either a mixture of or hexanes and EtOAc or a mixture of CH2CI2 and a 90:9:1 mixture of CH2CI2/CHjOH/concentrated NH4OH} or C- 18 reversed phase column chromatography (typical eluents included CCN and H20) to afford the desired carboxamide XX. The product structure was verified by 1H NMR and by mass analysis. Example 2: (lH-1, 2, 4-Triazol-3-yl) ( ( 3a, 5R, 6aS) -5- (2- (trifluoromethyl)phenyl>hexahydrocyclopenta fc]pyrrol-2 (IH) -yl) methanone 18) Step A: Following general procedure GP-A1 , (3aR, 5S, 6aS) -5- (2- (trifluoromethyl) henyl) octahydrocyclopenta [c] yrrole hydrochloride and IH-l , 2 , 4-triazole-3-carboxylic acid were converted to (1H-1,2,4- triazol-3-yl) ( (3ai, SR, 6&S) -5- (2- (trifluoromethyl(phenyl) hexahydrocyclopenta[c]pyrrol-2 (IH) -yl)methanone as a white solid (0.071 g, 52%): NMR (500 MHz, CDC13) delta 12.7.1 (bs, IH) , 8.12 (bs, IH) , 7.67 (m, IH), 7.49 (m, 2H) , 7.26 (m, IH) , 4.43 (m, 2H) , 3.93 (m, 2H) , 3.53 (m, IH) , 3.08-2.81 (m, 2H) , 2.42 (m, 2H) , 1.65 (m, 2H) ; ESI MS m/z 351 [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 4928-87-4, its application will become more common.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; PETRUKHIN, Konstantin; CIOFFI, Christopher; JOHNSON, Graham; DOBRI, Nicoleta; FREEMAN, Emily; CHEN, Ping; CONLON, Michael; ZHU, Lei; WO2014/152018; (2014); 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. 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole, A new synthetic method of this compound is introduced below., category: Triazoles

To a stirred solution of EE-3 (10 g, 44.08 mmol) in DMF (60 mL) is added K2C03 (9.158 g, 66.12 mmol) at room temperature then the reaction mixture is stirred at room temperature for 1 hour. EE-4 (5.422 g, 44.08 mmol) is added and the reaction mixture is stirred at room temperature for 12 hours. The reaction mixture is quenched with water then extracted with EtOAc twice. The organics are combined and concentrated. The residue is purified by column chromatography on silica gel eluting with EtOAc in heptane to yield Intermediate EE-5.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HUGHES, Robert Owen; LI, Xiang; NEMOTO, Peter Allen; SMITH KEENAN, Lana Louise; WU, Lifen; XIONG, Zhaoming; (65 pag.)WO2018/111803; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 288-88-0, name is 1H-1,2,4-Triazole, molecular formula is C2H3N3, 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: C2H3N3

STR6 A solution of 17.9 g (0.075 mole) of 2-(4-chlorophenylethyl)-2-tert.-butyloxirane and 6.9 g (0.1 mole) of 1,2,4-triazole in 30 ml of ethanol in a sealed tube is heated at 150 C. for 20 hours. The tube is allowed to cool and the reaction solution is evaporated. The residue is dissolved in ether, washed three times with water and once with sodium chloride solution, dried over sodium sulphate and evaporated. The residue is chromatographed over a column of silican gel (mobile phase: dichloroethane/ethyl acetate 1:1). 12.3 g (53.2% of theory) of 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-3-pentanol are obtained as a viscous oil. The hydrochloride of melting point 212 C. is obtained in virtually quantitative yield by customary reaction with ethereal hydrogen chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-88-0, its application will become more common.

Reference:
Patent; Bayer Aktiengesellschaft; US4668660; (1987); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 41253-21-8, 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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

2-(lH-l,2,4-Triazol-l-yl)benzonitrile. A suspension of 2-fluorobenzylnitrile (3.0 g, 25 mmol) and 1,2,4-triazole sodium salt (2.4 g, 27 mmol) were stirred in tetrahydrofuran (7 mL) and dimethylformamide (14 mL) at 95 0C for 18 h. After cooling and concentrating, the product was crystallized from hot CH2Cl2/hexane (1:1) to give the title compound as a white solid (4.25 g, 100% yield). 1H-NMR (300 MHz, CDCl3) 6 ppm: 8.74 (IH, s), 8.16 (IH, s), 7.82 (IH, dd, J= 4.9,1.3 Hz), 7.77-7.25 (2H, m), 7.57-7.51 (IH, m). LCMS [M+H]+ calcd for C9H7N4: 171.06; found: 171.12.

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, Sodium 1,2,4-triazol-1-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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: C2H3N3

2-iodobenzoic acid (1 g, 4.03 mmol), 2H-l,2,3-triazole (0.334 g, 4.84 mmol), copper(I) iodide (0.768 g, 4.03 mmol), cesium carbonate (2.63 g, 8.06 mmol) were reacted in DMF at 120 C under microwave irradiation for 20 minutes. Then the reaction was monitored confirming the presence of the required product. Large amount of starting material resulted left. The reaction was further irradiated for 20 minutes at 120 C. Solvent was then removed under vacuum, poured into water (100 ml) and neutralised with 37% HC1. Aqueous phase was extracted with Et20 (3×100 ml), and the collected organic phases were concentrated to give 1 g of crude material. This was purified with Biotage SP1 (over a 340g C18 column) eluting with a gradient of ACN and water (modified with 0.5% HCOOH). Fractions were collected and concentrated under vacuum to give the title compound D43 as colourless solid (140 mg). UPLC (GEN QC Basic): rt = 0.29 minutes, peak observed: 188 (M-l) C9H7N302 requires: 189. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 6.47 (br. s., 1 H) 7.47 – 7.59 (m, 1 H) 7.66 (t, 1 H) 7.75 – 7.87 (m, 3 H) 7.91 (d, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-36-8, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89606; (2012); 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. 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, A new synthetic method of this compound is introduced below., Safety of 4-[1,2,4]Triazol-1-yl-benzaldehyde

L-Proline (1.81 g, 15.6 mmol) was added to a stirring, heterogeneous mixture of 4-(1H-1,2,4-triazol-1-yl)benzaldehyde (13.5 g, 78.0 mmol, Intermediate 45, step a) and 2,2-dimethyl-1,3-dioxane-4,6-dione (11.2 g, 78.0 mmol) in ethanol (520 mL) at 23 C. After 1.5 hours, diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (19.7 g, 78.0 mmol) was added in one portion. After 16 hours, the ethanol was removed by rotary evaporation at 35 C. to afford a yellow solid. Isopropanol (300 mL) was added and the heterogeneous mixture was stirred for 10 minutes at 23 C. The mixture was filtered and the filter cake was washed with isopropanol (150 mL). The solids were collected and dried under vacuum to provide the titled compound as a white solid.

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; 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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); 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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3,5-Diamino-1,2,4-triazole

2-acetylthiophene (8.20 g) and N,N-dimethylformamide diethyl acetal (13.6 mL) were heated to reflux at 130¡ãC in xylene (13 mL) for two days. The reaction liquid was concentrated under reduced pressure, and after subjected to azeotropic distillation with toluene, crystallized with a mixed solvent of toluene-hexane and 3-dimethylamino-1-thiophen-2-ylpropenone (11.52g, yield 98percent) was obtained. The obtained 3-dimethylamino-1-thiophen-2-ylpropenone (10.78 g) was dissolve in toluene (160 mL) and stirred at 100¡ãC with 3,5-diamino-1,2,4-triazole (14.15 g) added. After 10-camphor sulfonic acid (13.82 g) was added, it was heated to reflux for 1.5 hours. After having cooled to room temperature, the supernatant was removed (decantation). The residue was suspended and washed with 5percent sodium carbonate/10percent ethanol aqueous solution, 10percent ethanol water, absolute ethanol and methylene chloride in this order and dried under reduced pressure and the title compound was obtained (8.55 g, yield 66percent).

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; NIPPON KAYAKU KABUSHIKI KAISHA; EP1674454; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3641-08-5, name is 2H-1,2,4-Triazole-3-carboxamide, 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 3641-08-5, Product Details of 3641-08-5

EXAMPLE 9 Preparation of 1(and 2 and 4)-Palmitoyl-s-triazole-3-carboxamide To a cooled, stirred mixture of 3 g. of 1,2,4-triazole-3-carboxamide and 7.4 g. of palmitoyl chloride in 125 ml. of anhydrous diethyl ether is added rapidly 2.75 g. of triethylamine. The cooling bath is removed and the mixture is stirred. at room temperature for 24 hours. The mixture is filtered and the solid is washed successively with diethyl ether, cold water, diethyl ether and then dried in vacuo for 4 hours. The solid is extracted with hot dry acetonitrile and cooled yielding a colorless solid. The solid is redissolved by heating the mixture and allowed to recrystallize from the clear, colorless solution. The product is collected, washed with acetonitrile and dried in vacuo for 3 hours, yielding 0.75 g., m.p. 145-160 C. (dec.).

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, 2H-1,2,4-Triazole-3-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; American Cyanamid Company; US4006159; (1977); A;,
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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 4928-87-4

A mixture of lH-1 ,2,4-triazole-3-carboxylic acid (8 mg, 0.07 mmol), EDCI (20 mg, 0.1 mmol), and 1-hydroxybenzotriazole (9 mg, 0.07 mmol) in DMF (1 mL) was slightly warmed up to a homogeneous solution which was added into a stirred solution of 5~(8- azabicyclo [3.2.1 ]octan-3 -yl)-7-(6-phenylpyridin-3 -yl)-2,4-dihydro- 1 H-[ 1 ,3]oxazino[5 ,4- e]pyrazolo[l,5-a]pyrimidine TFA salt (0.07 mmol) and N,N-diisopropylethylamine (37 mu,, 0.2 mmol) in DMF (2mL). It was stirred further for 10 min at room temperature. This crude compound was purified by HPLC to afford (3-(7-(6-phenylpyridin-3-yl)-2,4-dihydro-l FIJI, 3]oxazino[5,4-e]pyrazolo[l,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2. l]octan-8-yl)(4H-l?2,4- triazol-3-yl)methanone. LCMS t = 3.20 Min (10 min run, UV254nm). Mass calculated for M+ H 534.0, observed LC/MS m/z 534.0 (M+H).

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; SCHERING CORPORATION; MENG, Zhaoyang; NAN, Yang; PATEL, Mehul; SIDDIQUI, M. Arshad; REDDY, Panduranga Adulla, P.; SUN, Binyuan; WO2012/27240; (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. 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C3H6N4

(a) Ethyl 3-oxo-3-(pyridin-2-yl)propanoate (400mg, 2.07mmol) was taken in AcOH (10mL) in a 50mL round bottom flask under N2. To it was added 5-methyl-4H-1,2,4-triazol-3-amine (334mg, 2.49mmol). The reaction mixture was heated at 115C for 12h. The reaction mixture was then evaporated to dryness using toluene as an azeotropic solvent and triturated with diethyl ether. This was finally dried under high vaccum which affored 66a as a brown solid (350mg, 75%). This was then used in the next step without any further purification. LCMS(ESI) m/z 226.03 [M-H+]; 56% (purity).

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 4923-01-7.

Reference:
Article; Zuniga, Edison S.; Korkegian, Aaron; Mullen, Steven; Hembre, Erik J.; Ornstein, Paul L.; Cortez, Guillermo; Biswas, Kallolmay; Kumar, Naresh; Cramer, Jeffrey; Masquelin, Thierry; Hipskind, Philip A.; Odingo, Joshua; Parish, Tanya; Bioorganic and Medicinal Chemistry; vol. 25; 15; (2017); p. 3922 – 3946;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics