Day: March 10, 2021

252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, 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: 252742-72-6

1-200: N2-(3-Aminosulfonyl-4-fluorophenyl)-5-fluoro-N4-[4-(254-dihydro-3-oxo-l,2,4- triazol-5-yl)methyleneoxyphenyI]-2,4-pyrimidinediamine (76); [0719] To a solution of 5-chloromethyl-2,4-dihydro-l ,2,4-triazol-3-one (35 mg, 0.26 mmol) in 2-butanone, were added N2-(3-aminosulfonyl-4-fluorophenyl)-5-fluoro-N4-(4- hydroxyphenyl)-2,4-pyrimidmediamme (100 mg, 0.25 mmol) and potassium carbonate (35 mg, 0.25 mmol). The resulting mixture was micro waved at 140 0C for 5 hours, and then additional of 5-chloromethyl-2,4-dihydro-l,2,4-triazol-3-one was added as needed The reaction solvent was removed under a reduced pressure, and the residual was purified by column chromatography (silica gel, dichloromethane: methanol 8:2 v/v) to give 25 mg of N2- (3-aminosulfonyl-4-fluorophenyl)-5-fluoro-N4-[4-(2,4-dihydro-3-oxo-l,2,4-triazol-5- yl)methoxyphenyl]-2,4-pyrimidinediamine (76) as a light yellow solid. 1H NMR (D2O): delta 7.90-7.89 (d, J= 3 Hz, 1H), 7.60-7.58 (d, J= 6 Hz, 1H), 7.34 (bs, 2H), 7.24-7.18 (m, 2H), 7.05-7.02 (d, J= 9.0 Hz, 2H), 6.65-6.62 (d, J= 9.0 Hz, 2H), 5.11 (br s, 2H); LCMS (m/z): 491.05 (MH+).

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2006/133426; (2006); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-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. name: 1H-[1,2,3]Triazole-4-carboxylic acid

(R)-4-Amino-5-(5?-chloro-2?-fluorobiphenyl-4-yl)-2-ethyl-2-hydroxymethylpentanoic acid (isomer a; 85 mg, 190 mumol, 1.0 eq.) and DIPEA (250 muL, 1.4 mmol, 7.5 eq.) were dissolved in DMF (800 muL). 1H-1,2,3-triazole-4-carboxylic acid (32 mg, 290 mumol, 1.5 eq.), HATU (70 mg, 184 mumol, 1.0 eq.), and DIPEA (100 muL, 572 mumol, 7.5 eq.) were dissolved in DMF (500 muL) and stirred at room temperature for 15 minutes. The solutions were then combined and the resulting mixture stirred at room temperature for 20 minutes and when the reaction was complete (as determined by LC/MS analysis), the mixture was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer a; 21.9 mg). LCMS (ESI): calc. C23H24ClFN4O4=474; obs. M+H=475.1. Retention time: 4.75 min. [0432] (R)-4-Amino-5-(5?-chloro-2?-fluorobiphenyl-4-yl)-2-ethyl-2-hydroxymethylpentanoic acid (isomer b; 85 mg, 190 mumol, 1.0 eq.) and DIPEA (250 muL, 1430 mumol, 7.5 eq.) were dissolved in DMF (800 muL). 1H-1,2,3-triazole-4-carboxylic acid (32 mg, 290 mumol, 1.5 eq.), HATU (70 mg, 184 mumol, 1.0 eq.), and DIPEA (100 muL, 572 mumol, 7.5 eq.) were dissolved in DMF (500 muL) and stirred at room temperature for 15 minutes. The solutions were then combined and the resulting mixture stirred at room temperature for 20 minutes and when the reaction was complete (as determined by LC/MS analysis), the mixture was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer b; 37.8 mg). LCMS (ESI): calc. C23H24ClFN4O4=474; obs. M+H=475.0. Retention time: 4.72 min. [0433] LC/MS Method: flow rate: 1.5 mL/min; Buffer A: 0.1% TFA/H2O; Buffer B 0.1% TFA/MeCN; gradient elution from 5%-100% B over 9.6 min, then 100% B for 1.0 minute, detection at 254 nm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-70-2, its application will become more common.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/209352; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-70-2, These common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-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.

H. (2S,4S)-5-Biphenyl-4-yl-2-hydroxymethyl-4-[(3H-[1,2,3]-triazole-4-carbonyl)-amino]-pentanoic acid 2-methanesulfonyl-ethyl ester (R7=-(CH2)2SO2CH3) (2S,4S)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-pentanoic acid (100 mg, 250 mumol, 1.0 eq.), HOBt (0.1 g, 750 mumol, 3.0 eq.), and EDCI (130 muL, 3.0 eq.) were dissolved in DCM (2 mL). After stirring for 10 minutes, 2-(methylsulfonyl)-ethanol (250 mg, 2.0 mmol, 8.0 eq.) and 4-methylmorpholine (110 muL, 4.0 eq.) were added. The resulting mixture was stirred at room temperature for 1.5 hours. The reaction was quenched with water. The DCM layer was separated, concentrated, and the product purified by flash chromatography (70-100% EtOAc/hexanes over 15 minutes). The clean fractions were combined and concentrated. MeCN (2.5 mL) and 4 M of HCl in dioxane (250 muL, 4.0 eq.) were added and the resulting mixture was stirred at room temperature for 1 hour. The solvent was removed to provide the intermediate HCl salt, which was used in the following coupling step. 1,2,3-Triazole-4-carboxylic acid (28.3 mg, 250 mumol, 1.0 eq.) and HATU (95.2 mg, 250 mumol, 1.0 eq.) were dissolved in DMF (2.0 mL) and the resulting solution was stirred for 5 minutes, followed by the addition of DIPEA (131 muL) and the intermediate HCl salt. After 5 minutes, the reaction was quenched with water and the product purified by preparative HPLC to yield the title compound (64 mg; purity 95%). MS m/z [M+H]+ calc’d for C24H28N4O6S, 501.17. found 501.4.

Statistics shows that 1H-[1,2,3]Triazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 16681-70-2.

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 202931-88-2, name is 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde, 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 202931-88-2, Safety of 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde

General procedure: A solution of 19 (300 mg, 0.70 mmol) in tetrahydrofuran (3 mL) was slowly added to a solution of lithium diisopropylamide (LDA) in heptane/tetrahydrofuran/ethylbenzene (2 M, 0.38 mL, 0.76 mmol) at 78oC, and the resultant solution was stirred at -78oC for 30 minutes. Chlorotitanium triisopropoxide (1 M, 2.8 mL) was then added slowly, and the resulting mixture was stirred at 40oC for 1 hour. The reaction was cooled to -78oC, and propionaldehyde (49 mg, 0.84 mmol) was added slowly. This mixture was then warmed to 40oC, and stirred at 40oC for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (1 mL), diluted with 10 mL of tetrahydrofuran, and treated with Celite for 1 hour. The resultant slurry was filtered and concentrated. The resultant residue was purified by silica gel chromatography (gradient: 95:5 hexanes:ethyl acetate to 65:35 hexanes:ethyl acetate) to provide 20 as a white solid. Yield: 230 mg, 68%.

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-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Warmus, Joseph S.; Quinn, Cheryl L.; Taylor, Clarke; Murphy, Sean T.; Johnson, Timothy A.; Limberakis, Chris; Ortwine, Daniel; Bronstein, Joel; Pagano, Paul; Knafels, John D.; Lightle, Sandra; Mochalkin, Igor; Brideau, Roger; Podoll, Terry; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2536 – 2543;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 31250-99-4, 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. 31250-99-4, name is 1-Trityl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 6 This Example illustrates the preparation of 1-trityl-3-bromo-1,2,4-triazole. A stirred solution of 1-trityl-1,2,4-triazole (15.55 g, prepared as described in Example 1) and N,N,N’,N’-tetramethylethylenediamine (5.8 g) in dry tetrahydrofuran (500 ml) was cooled to -70 C. under nitrogen and treated dropwise with n-butyllithium (37.5 ml, 1.6M in hexane). The deep-red solution was stirred at -70 C. for twenty minutes, then treated dropwise with a solution of bromine (10.4 g) in dry tetrahydrofuran (10 ml). The now brownish-yellow solution was allowed to warm to -20 C., quenched with 0.1M sodium thiosulphate solution (150 ml), and extracted with dichloromethane (500 ml). The organic layer was washed with water (4*100 ml), dried and evaporated. The residue was chromatographed on silica, using dichloromethane-ether (25:2) as eluant, to give 1-trityl-5-bromo-1,2,4-triazole (7.86 g, m.p. 239-241 C.). NMR (CDCl3):delta7.1-7.3(15H,m), 7.95(1H,s).

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

Reference:
Patent; Zeneca Limited; US5393732; (1995); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

Then, an amidation step is carried out, the reaction equation being as follows: The 1.49g (15mmol, 1eq) of the compound of Formula III-1 3,5-amino-1,2,4-triazole, 3.64 g (36 mmol, 2.4 eq) of triethylamine were dissolved in 50 mL of dichloromethane,50 mL of a dichloromethane solution containing 9.39 g of the compound shown by the formula 11-1 (4- (4′-nitrophenyl) benzoyl chloride) was slowly added dropwise at 0 ¡ã C. After completion of the dropwise addition,The reaction solution was allowed to react at room temperature for 24 h,Subsequently, the reaction solution was washed with 200 mL of pure water, After the layers were separated, the organic phase was washed twice with saturated sodium carbonate solution and then dried over anhydrous magnesium sulfate,The organic phase was evaporated to give a crude product,The crude product was recrystallized to give 6.52 g of the compound of formula IV-1,The yield was 80percent.

The synthetic route of 1455-77-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fuyang Xinyihua Material Technology Co., Ltd; Wu, Jingwei; (17 pag.)CN105294664; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 423165-07-5, 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 423165-07-5 as follows.

General procedure: To an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C.

According to the analysis of related databases, 423165-07-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Viveka, T. Lakshmi; Sharada, L. Nalanda; Asian Journal of Chemistry; vol. 30; 9; (2018); p. 2029 – 2034;,
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. 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 5-Amino-4H-1,2,4-triazole-3-carboxylic acid

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

Adding a certain compound to certain chemical reactions, such as: 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, 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 7411-23-6, Recommanded Product: 3,5-Dibromo-1H-1,2,4-triazole

To a colorless solution of 3,5-dibromo-lH-l,2,4-triazole (lnt-1, 250 mg, 1.1 mmol, Eq: 1) and 3-iodooxetane (243 mg,1.32 mmol) in DMF (3 ml) was added K2CO3 (305 mg, 2.2 mmol). The vial was closed under Argon and stirred over night at 120C. The reaction mixture was diluted with 25 mL H2O and extracted with EtOAc (2 x 25 mL) and the organic layers were washed with sat NaCl (3 x 25 mL), dried over MgS04 and concentrated in vacuo. The title compound was isolated as a white solid (198 mg, 63.5 % yield). MS (ES+) m/z: 283.9 [(M+H)+].

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, 3,5-Dibromo-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

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

Adding a certain compound to certain chemical reactions, such as: 138624-97-2, name is 1-Benzyl-1H-1,2,4-triazole-3-carboxylic acid, 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 138624-97-2, Recommanded Product: 138624-97-2

M-10 (25 mg) was dissolved in 2 mL of dichloromethane and 1 mL of trifluoroacetic acid, and after 1 hour of reaction, the solvent was spin-dried to obtain the intermediate amine. Subsequently, the intermediate was dissolved in DMSO (1 mL), and 35 mg of acid-6 was added (the acid was purchased commercially, or the preparation of the acid please refer to: CN 105121432 A, J. Med. Chem. 2017, 60, 1247 ), HATU (56mg), DIPEA (60mg), the reaction was overnight, added water and ethyl acetate extraction, the organic layer was collected, dried over anhydrous sodium sulfate, vacuum rotary evaporation to remove the solvent, HPLC separation to obtain compound ZB-R-5.

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; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhou Bing; Tang Wei; Yang Xiangbo; Lu Huimin; Gao Mengying; Yang Yaxi; Feng Huijin; (69 pag.)CN111138448; (2020); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics