Tag: M.W:100-200

Synthetic Route of 626248-56-4, New Advances in Chemical Research in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 626248-56-4, name is 3-(2H-1,2,3-Triazol-2-yl)aniline, molecular formula is C8H8N4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

A mixture of tert-butyl (1 S,2R)-2-(3-bromo-4- cyanophenylamino)cyclohexylcarbamate (150 mg, 0.380 mmol), 3-(2H-l,2,3-triazol-2- yl)aniline (100 mg, 0.625 mmol), BINAP (40 mg, 0.064 mmol), Pd(OAc)2 (25 mg, 0.11 mmol) and K2C03 (150 mg, 1.08 mmol) in dioxane (3 mL) was degassed with Ar, then was stirred at 100 C for 4 h. EtOAc and water were added. The organic phase was separated, washed with IN HCl, then with 5% NaHC03, dried over Na2S04, concentrated in vacuo to give tert-butyl (lS,2R)-2-(3-(3-(2H-l,2,3-triazol-2-yl)phenylamino)-4- cyanophenylamino)cyclohexylcarbamate as a crude residue.

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Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong, J.; SONG, Yonghong; XU, Qing; KANE, Brian; BAUER, Shawn, M.; PANDEY, Anjali; WO2012/61418; (2012); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Product Details of 1001401-62-2

tgrt-butvU7Sr)-7-methyl-8-r2-(‘2H-1.2.3-triazol-2-v?benzoyll-5.8-diazaspiror2.61nonane-5- carboxylate (2-5); A solution of 1.26 g (3.8 mmol) 2jtheta in 40 mL MeOH was evacuated under reduced pressure and purged with N2 three times before adding a portion of palladium hydroxide on carbon. After purging three more times with N2, the atmosphere was replaced with H2 and the reaction was stirred under a balloon of H2 for 2 h. The reaction was filtered through a pad of celite by rinsing with EtOAc and MeOH, and the filtrate was concentrated to provide a colorless oil. This material was dissolved in 3 mL of DMF and to it was added 683 mg of 2j4 (3.6 mmol; prepared in an analogous fashion to J^, see example 1-C), 668 mg (4.3 mmol) 1- hydroxybenzotriazole hydrate, 1.5 mL (10.8 mmol) triethylamine and 831 mg (4.3 mmol) EDC and the reaction was stirred overnight at 60C. The reaction was partitioned between EtOAc and 10% aqueous citric acid, the layers were separated, and the organic was washed with water, brine, dried over Na2Stheta4 and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel (EtOAc/hexanes) to provide 2^5 as a white solid. Data for M: LC/MS: rt = 2.36 min; m/z (M + H) = 412.3 found; 412.2 required.

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law. In my other articles, you can also check out more blogs about 1001401-62-2, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/58238; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 81606-79-3, name is 2-(1,2,4-Triazol-1-yl)acetonitrile belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(1,2,4-Triazol-1-yl)acetonitrile

Step 1: l-(5-((4H-l,2,4-Triazol-4-yl)methyl)-2-(difluoromethoxy)benzyl)-6-bromo-2-meth l-l,2- dihydro-3H-indazol-3-one A mixture of 6-bromo- 1 -(5-(bromomethyl)-2-(difliioromethoxy)berizr ‘l)-2-methyl- 1 ,2-dihydro-3H- indazoi-3-one (Preparation 20, step 3) (0.100 g, 0.210 mmol) and 2-(lH-l,2,4-triazol-l-yl)acetonitrile {Synthesis 1995, 9, 1183-1189) (0.026 g, 0.210 mmol) in MeCN (1 mL) was heated at about reflux for about 6 h, after which additional 2~(lH-l,2,4-triazoi-l-yl)acetonitrile (0.020 g, 0.164 mmol) was added and heating continued for about 24 h. The reaction mixture was concentrated under reduced pressure and the residue was treated with 2 M aq. sodium hydroxide (2 mL, 4 mmol). After stirring for about 1 h, the mixture was extracted with EtOAc (3 x 5 mL) and the combined organic phases were washed with sat. aq. NaCl (5 mL), dried over Na2S04, filtered, and concentrated under reduced pressure. The sample was purified on silica gel using 0-5% MeOH with DCM to give the title compound (0.053 g, 54%); LC/MS (Table A, Method i) = 1.04 min; MS m/z: 464 and 466 X i 11 >

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Reference:
Patent; ABBVIE INC.; ARGIRIADI, Maria; BREINLINGER, Eric; DIETRICH, Justin, D.; FRIEDMAN, Michael; IHLE, David; MORYTKO, Michael; MULLEN, Kelly; OSUMA, Augustine; LO SCHIAVO, Gloria, Y.; WILSON, Noel, S.; (303 pag.)WO2016/168633; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 3641-13-2, New Advances in Chemical Research in 2021. As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 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, 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.

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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

Synthetic Route of 1001401-62-2, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic 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.

To a solution of compound 4 (1.0 g, 4.42 mmol) and 2-(2H-1,2,3-triazol-2- yl)benzoic acid (0.84 g, 4.42 mol) in DCM (50 mL) was added HATU (1.70 g, 4.50 mmol), DIPEA (0.60 g, 4.5 mmol) succesively. The solution was stirred at RT for 9 h under N2, then poured into water (30 mL) and extracted with DCM (20 mL x 3). The combined organic layerswere washed with brine (30 mL), dried over Na2504, filtered and concentrated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc = 7: 1 to 2 : 1) to give the title compound 5 (1.5 g,). LRMS m/z (M+H) 398.2 found, 398.2 required.

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Reference:
Patent; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (97 pag.)WO2016/100157; (2016); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 4922-98-9, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, 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: Solution A. A solution of KOH (0.56 g, 0.01 mol) and potassium salt of ethyl nitrocyanoacetate (1.96 g, 0.01 mol) in2 (8 ml) was stirred at room temperature for 3 h, then kept overnight. 4 M aqueous KOAc (8 ml, 0.03 mol) was added to the resulting solution, and the mixture cooled to 5°. A mixture of 3-aminoazole 1a?i (0.010 mol), EtOH (10 ml),H2O (10 ml), and concentrated HCl (2.5 ml, 0.030 mol)was treated with a solution of NaNO2 (0.759 g, 0.011 mol)in H2O (3 ml) at ?5 °. The reaction mixture was kept at this temperature for 10 min, then added to the solution A. The mixture was kept at room temperature for 1 h; the formed precipitate was filtered, stirred with 40percent aqueous H2SO4 (10 ml) (AcOH (10 ml) was used for compound 4e), filtered, and dried. The obtained hydrazone 3a?i was heated under reflux in DMF for 3 h. The solvent was evaporated, the residue triturated in water, filtered, and dried.

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Reference:
Article; Voinkov, Egor K.; Ulomskiy, Eugeny N.; Rusinov, Vladimir L.; Chupakhin, Oleg N.; Gorbunov, Evgeny B.; Drokin, Roman A.; Fedotov, Victor V.; Chemistry of Heterocyclic Compounds; vol. 51; 11-12; (2015); p. 1057 – 1060; Khim. Geterotsikl. Soedin.; vol. 51; 11-12; (2015); p. 1057 – 1060,4;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 129027-65-2, New Advances in Chemical Research in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic,A common heterocyclic compound, 129027-65-2, name is 1-(tert-Butyl)-1H-1,2,3-triazole-4-carbaldehyde, molecular formula is C7H11N3O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To a 250-mL round bottom flask was added a solution of 1-tert-butyl-1H-1,2,3-triazole-4-carbaldehyde (2.47 g, 16.1 mmol, 2.2 eq) in dichloroethane, followed by addition of propargyl amine (361 mg, 72 mmol, 1.0 eq). To this mixture sodium triacetoxyborohydride (3.8 g, 17.9 mmol, 2.5 eq) was added in one portion with vigorous stirring. The reaction mixture was stirred at room temperature for 40 h. 1N H2SO4 (86 mL) was added to the reaction, and the mixture was stirred for 15 min. The pH was adjusted to >10 by addition of potassium carbonate. The reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (3×300 mL). The organic layers were combined, dried over anhydrous MgSO4, and filtered. Solvent was removed and the residue was purified on column to afford the product as a white powder. 1H NMR complies with the reported value.

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Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCACATION; Zeng, Dexing; (26 pag.)US2017/297008; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-70-2, New Advances in Chemical Research in 2021.Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To a solution of tert-butyl-3,8-diazabicyclo[3.2.1 ]octane-3-carboxylate (0.3 mmol, 750 mu, 0.4 M) in DCE were added benzenesulfonyl chloride (0.45 mmol, 900 mu, 0.5M, 1 .5 eq) in DCE and 0.9 mmol DIPEA (156 mu, 3 eq) and the mixture was shaken overnight at RT. 2 mL TFA/DCE 3:1 were added and the mixture was shaken at RT for 3 h. After evaporation of the solvent, 1 H-1 ,2,3-triazole-5-carboxylic acid (0.6 mmol, 1 .2 mL, 2 eq, 0.5M) in NMP, 928 mu DIPEA (3.6 mmol, 12 eq; adjustment of pH to 8) and HATU (0.6 mmol, 1.2 mL, 2 eq, 0.5 M) in NMP were added and the mixture was shaken overnight to yield after preparative HPLC 26 mg (25%) of the title compound 3,8- diazabicyclo[3.2.1 ]oct-3-yl(1 H-1 ,2,3-triazol-4-yl)methanone.

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Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SIEBENEICHER, Holger; STEUBER, Holger; TER LAAK, Antonius; NUBBEMEYER, Reinhard; ROTTMANN, Antje; IRLBACHER, Horst; BADER, Benjamin; PETERS, Michaele; WAGENFELD, Andrea; TEREBESI, Ildiko; (123 pag.)WO2017/202817; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 252742-72-6, New Advances in Chemical Research in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, molecular formula is C3H4ClN3O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Reference Example 108; 5-({[(4-bromophenyl)methyl]thio}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one; [Show Image] To a solution of 5-(chloromethyl) -2,4-dihydro-3H-1,2,4-triazol-3-one obtained according to the methods described in Tetrahedron Letter, 2000, 41, 8661 and the like (2.00 g, 15.0 mmol), (4-bromophenyl)methanethiol (3.04 g, 15.0 mmol) and potassium carbonate (2.48 g, 0.369 mmol) in THF (4 mL) was added a suspension of O-(trimethylsilyl)hydroxylamine (0.271 mL, 18.0 mmol) in DMF (40 mL) at room temperature, and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. The solid was washed with water and diethyl ether to give the title compound as a white powder (3.97 g, 88percent). 1H-NMR (300MHz, DMSO-d6) delta: 3.36 (2H, s), 3.70 (2H, s), 7.28 (2H, d, J = 8.3 Hz), 7.52 (2H, d, J = 8.3 Hz), 11.29 (1H, br), 11.39 (1H, br).

I am very proud of our efforts over the past few months and hope to 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one help many people in the next few years.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1953148; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 1001401-62-2, New Advances in Chemical Research in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, molecular formula is C9H7N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Asolution of 2- (2H-1, 2, 3-triazol-2-yl) benzoic acid (6.8 g, 36 mmol) in SOCl2(30 mL) was stirred at RT for 30 mins. The solvent was removed in vacuo. To asolution of the product from Step 2 (6.0 g, 36 mmol) in dry toluene (50 mL) wasadded 1 N aqueous NaOH (73 mL, 0.073 mol) at 0 and asolution of the above residue in toluene (30 mL) dropwise . The resultingmixture was stirred at RT overnight and extracted with EtOAc (100 mL x 3) . Thecombined organic layers were washed with brine, dried over Na2SO4,filtered, and concentrated in vacuo to give the title compound as an oil, whichwas used without further purification. LRMS m/z (M+H) 508.1 found, 508.2required

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Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; LUO, Yunfu; (47 pag.)WO2016/65587; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics