Tag: M.W:100-200

New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Bromo-1H-1,2,4-triazole

Sodium hydride (1.2eq) was added to a solution of 3-bromo-lH-[l,2,4]triazole (leq) in dry DMF (2.3ml/mmol) at 00C and under an atmosphere of nitrogen The solution was stirred at 00C for 20min, then, SEM-Cl (1.2eq) was added. The mixture was stirred at room temperature overnight and diluted with H2O and ethyl acetate. The organic layers was washed with H2O then brine, dried on anhydrous Na2SO4, filtered and concentrated in vacuum to give the titled compound. Crude compound 3- bromo-l-(2-trimethylsilanyl-ethoxymethyl)-lH-[l,2,4]triazole was engaged in step 2 without purification. IH-NMR (CDCl3): delta (ppm) 0.00 (t, 9H); 0.92 (t, 2H); 3.64 (t, 2H); 5.44 (s, 2H); 8.13 (s, IH)

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Reference:
Patent; VIVALIS; BERECIBAR, Amaya; GUEDAT, Philippe; MOHAMED-ARAB, Celine; WO2011/4017; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 135242-93-2, 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. 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, molecular formula is C4H7N3O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To a mixture of (l-methyl-l/-/-l,2,4-triazol-3-yl)methanol (400 mg, 3.54 mmol) and iodobenzene diacetate (1.25 g, 3.89 mmol) in dichloromethane (10 mL) was added TEMPO ((2, 2,6,6- tetramethylpiperidin-l-yl)oxyl) (56 mg, 354 pmol). The mixture was stirred at 15-20C for 2h. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ethenethyl acetate = 1:2) to give l-methyl-l/-/-l,2,4-triazole-3-carbaldehyde (300 mg, 2.70 mmol, 76% yield). XH NMR (chloroform-d 400 MHz) d 10.01 (s, 1H), 8.19 (s, 1H), 4.06 (s, 3H).

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Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (278 pag.)WO2019/115567; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 13273-53-5, 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. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, 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 the crude (S)-4-(2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide (30 mg, 0.059 mmol) in residual dioxane was added 4-bromo-1-methyl-1H-1,2,3-triazole (14.24 mg, 0.088 mmol), PdCl2(dppf) (42.9 mg, 0.059 mmol), DME (195 mul) and 2 M Na2CO3 (130 mul) at room temperature. The reaction mixture was stirred for 5 h. After water and EtOAc were added, the organic layer was extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered off, and concentrated in vacuo. The crude product was purified by prep HPLC. The pure fractions were lyophilized yielding (S)-4-(2-amino-5-(1-methyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide as a TFA salt (25% over 2 steps). LCMS (m/z): 467.3 (MH+), 0.61 min; 1H NMR (400 MHz, CD3OD) delta ppm 8.64 (m, 1H), 8.31 (m, 1H), 8.25 (m, 2H), 8.2 (m, 1H), 7.82 (m, 1H), 7.4 (m, 3H), 7.28 (m, 2H), 7.22 (m, 1H), 5.11 (m, 1H), 4.07 (s, 3H), 3.78 (m, 2H).

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Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Product Details of 15988-11-1

General procedure: A mixture of dimedone (1, 1 mmol), 4-phenylurazole (2, 1 mmol), aromatic aldehyde (3a-h, 1mmol) and S-LCCO nano perovskite (0.01 g) was mixed in a high-pressure Teflon reactor, which was equipped with a magnetic stirrer and an optical fiber, which was implemented to control the reaction’s temperature. The reaction mixture was irradiated by 400 W microwave at 80 oC, for the specified reaction times. TLC with n-hexan:ethylacetate eluent was used to monitor the progress of the reactions. After reaction completion and cooling, the reaction mixtures were filtered and washed with ethanol to separate the catalyst. First, 10 mL water was added to the solution. Then, EtOH/H2O (4:1) was added to crystallize the water insoluble crude products. Then the crystals were filtered to achieve pure products (4a-h).

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 15988-11-1, and we look forward to future research findings.

Reference:
Article; Zahedi, Najmeh; Javid, Ali; Mohammadi, Mohammad Kazem; Tavakkoli, Haman; Bulletin of the Chemical Society of Ethiopia; vol. 32; 2; (2018); p. 239 – 248;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 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. HPLC of Formula: C3H3N3O2

Compound 2 (35 mg, 83 mumol) was combined with HATU (38 mg, 100 mumol), 1H-[1,2,3]triazole-4-carboxylic acid (12.3 mg, 108 mumol) in DMF (0.5 mL). DIPEA (43.7 muL, 250 mumol) was added and the mixture was stirred for 2 hours. EtOAc was added, followed by a saturated aqueous NH4Cl solution. The mixture was stirred for 10 minutes then concentrated under reduced pressure to yield Compound 3.

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Reference:
Patent; Fleury, Melissa; Hughes, Adam D.; US2014/45906; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 7343-33-1, New Advances in Chemical Research in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, molecular formula is C2H2BrN3, 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 reaction flask was added 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol) and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with nitrogen gas, and then DMSO (33.8 ml) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 20 hours (h). The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite®. The Celite® was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography using EtOAc/hexanes as eluent to yield the title compound (3.78 g, 73percent): mp 69-70° C.; 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta ?58.04; EIMS m/z 307 ([M]+).

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Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; WHITEKER, Gregory T.; US2014/275560; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-70-2, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 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.

To a stirred solution of 2S,45)-4-amino-5-biphenyl-4-yl-2-(2- hydroxyethoxymethyl)pentanoic acid ethyl ester (17 mg, 47 muiotaetaomicron) in DMF (0.3 mL), was added lH-l,2,3-triazole-4-carboxylic acid (5.3 mg, 47 muiotaetaomicron) and HATU (18 mg, 47 muetaiotaomicron), followed by DIPEA (25 mu^, 141 muetaiotaomicron). The mixture was stirred for 30 minutes, then concentrated under reduced pressure to yield crude Compound 1, which was used in the next step without purification.

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Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FLEURY, Melissa; BEAUSOLIEL, Anne-Marie; HUGHES, Adam D.; LONG, Daniel D.; WILTON, Donna A.A.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 13273-53-5, 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, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

General procedure: To a 50 mL round bottle flask was added 1,1?-Bis(diphenylphosphino)ferrocenedichloro Palladium(II) (0.1equiv), bromide (1.0equiv) and vinylboronic acid pinacol ester (2.0equiv) in 20mL dioxane. The mixture was degassed for 5min, and sodium carbonate aqueous solution (2.0M, 10equiv) was added. The mixture was then heated to 85C for 14h. After cooled to rt, the reaction mixture was filtered through a short Celite pad and washed with EtOAc. The organic solution was concentrated under reduced pressure and the residue was loaded into combi flush for purification to afford the product as oil.

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Reference:
Article; Lian, Yajing; Burford, Kristen; Londregan, Allyn T.; Tetrahedron; vol. 71; 50; (2015); p. 9509 – 9514;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 4928-87-4, 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, 4928-87-4, name is 1,2,4-Triazole-3-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.

Example 2. Synthesis of N-{4-[(pyrimidin-2-yl)sulfamoyl]phenyl}-lH-l,2,4- triazole-3-carboxamide, 1-18 1-18 [00267] Compound 1-18 was prepared according to the reaction sequence in Scheme IV with several adaptations. The solvent was removed in vacuo, the remaining material was triturated from H2O/CH3CN 1 : 1 (20ml), washed with small volumes of DMSO/CH3CN 1 :2, collected and dried to afford 190mg (65%) of N-{4-[(pyrimidin-2-yl)sulfamoyl]phenyl}-lH-l,2,4-triazole-3- carboxamide 1-18 as a colourless solid. 1H NMR (500 MHz, DMSO-d6) delta 14.84 (s, 1H), 11.70 (s, 1H), 10.83 (s, 1H), 8.66 (s, 1H), 8.50 (d, J = 4.9 Hz, 2H), 8.02 (d, J = 8.9 Hz, 2H), 7.95 (d, J = 8.9 Hz, 2H), 7.04 (t, J = 4.9 Hz, 1H).

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Reference:
Patent; RAZE THERAPEUTICS, INC.; SAIAH, Eddine; (148 pag.)WO2016/40449; (2016); 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. 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Phenyl-1H-1,2,4-triazol-3-amine

Example 38; STEP A; To the solution of 3-phenyl-1H-1 ,2,4-triazol-5-amine (32 mg, 0.2 mmol) in DMA (0.5 ml_) was added ethyl 4-chloro-4,4-difluoro-3-oxobutanoate (40 mg, 0.2 mmol). The reaction mixture was stirred in microwave at 180 0C for 20 minutes, and then cooled to room temperature. The product, compound 38-1 , was purified by reverse phase HPLC.

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Reference:
Patent; SCHERING CORPORATION; SHIPPS, JR., Gerald, W.; CHENG, Cliff, C.; HUANG, Xiaohua; ACHAB, Abdelghani, Abe; ORTH, Peter; VOIGT, Johannes, H.; SOUCY, Kyle, Ann; WO2010/56631; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics