Day: August 4, 2021

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. 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Product Details of 3641-13-2

Example 1 – Preparation of an Azo Compound; In this example the desired pH for the coupling reaction between a diazotised amine and a coupling component was a pH in the range 7 to 9.(a) Preparation of Coupling Component StreamNaphthalene-2-hydroxy-3,6-disulphonylamino-4-benzoic acid (0.91 mol) was dispersed in water (8.3kg). Once charging was complete, the pH was adjusted to 7-8 using 47% sodium hydroxide solution. Agitation was continued until dissolution was complete. The volume was made up to 9.2L by the addition of further water as required.(b) Preparation of Amine and Nitrite Solution3-Amino-1,2,4-triazole-5-carboxylic acid (1.27mol) was dissolved in water (2.9kg) at 45C, pH 9. The pH was maintained at 9 to 10 by addition of 47% sodium hydroxide solution as required. The solution was cooled to room temperature and sodium nitrite (1.33mol) was added. Stirring was continued until dissolution was complete. The volume was made up to 3.2L by the addition of further water as required.(c) Continuous Manufacture of Desired ProductThe reaction apparatus consisted of a number of feed vessels and pumps, two reactors, a product hold tank (or “buffer vessel”) and containers for the collection of product.The first reactor was a small continuous stirred tank reactor for the production of the diazonium salt. This reactor was assembled such that the overflow (i.e. outlet) stream from this reactor would flow into the second reactor.The second reactor consisted of a length of flexible tubing arranged in a “loop”. Into this loop were fitted a centrifugal recirculation pump, a flow meter, a pH sensor, inlet ports for diazonium salt, coupling component stream and sodium hydroxide stream for pH adjustment and an exit port for the desired chemical compound. A flow meter and inlet port for diazonium salt were positioned downstream of the recirculation pump and the exit port was positioned still further downstream, such that the majority of the tubing length lay between the inlet port for the diazonium salt and the exit port. The exit port was located at the highest point of the loop reactor. The coupling component and sodium hydroxide inlet ports, and a pH sensor, were fitted between the exit port and the inlet (“suction side”) of the recirculation pump.Prior to start-up, the loop reactor was filled with water and the recirculation pump was started. The flow rate was adjusted to approximately 4 litres per minute (approximately 240L/h) at the outlet of the recirculation pump. The exit port was initially directed to a waste receiver. The reagent feed pumps were set to the correct flow rates as given below and the diazonium salt precursors, coupling component and sodium hydroxide solution were charged to the appropriate feed vessels.A small amount of sodium hydroxide was then fed into the loop to raise the pH to pH to approximately pH 10. The coupling component feed pump was started, such that coupling component stream entered the loop. The flow was allowed to continue until coupling component was present throughout the loop and the pH had stabilised at 8.5-9.5. The coupling component pump was then stopped.The agitator in the first reactor (where the diazonium salt will be prepared) was switched on. The amine / sodium nitrite feed and hydrochloric acid feed pumps were started, giving flows of 7.7 litres per hour and 4.2 litres per hour respectively of the amine/nitrite solution and the hydrochloric acid solution into the first reactor to form a diazonium salt. The first reactor was allowed to fill.Once the first reactor had filled, the coupling component feed pump was restarted (giving a flow of 22.1 litres per hour) and diazonium salt slurry formed in the first reactor was allowed to flow into the loop reactor. Via the inlet port. The pH of the coupling component in the loop reactor was maintained at approximately 9 by feeding in sodium hydroxide at an appropriate rate (a variable speed pump and pH controller were used to achieve this). A distinct colour change was observed to spread through the loop reactor from the diazonium salt inlet port, indicating the formation of the desired chemical compound (an azo dye). The desired chemical compound overflowed from the loop reactor via the exit port at a rate of approximately 37 litres per hour. The recycled flow therefore exceeded the throughput by a factor of approximately 6, therefore the Recirculation Ratio was about 6. This recycled stream of desired chemical compound provided pH buffering for subsequent cycles of the loop, such that the desired chemical compound was obtained consistently at approximately pH8.It was found that the loop reactor took a few residence times to achieve steady state, so the first 2.5 litres of product were discarded and the second 2.5 litres were collected and analysed separately from the bulk.The desired chemical compound was obtained in good yield and purity.

I hope this article can help some friends in scientific research. I am very proud of our efforts over the past few months and hope to 5-Amino-4H-1,2,4-triazole-3-carboxylic acid help many people in the next few years.

Reference:
Patent; AVECIA INKJET LIMITED; WO2006/8495; (2006); A1;,
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. 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

Step 3: 3,5-Dichlorobenzyl 4-(3-(1H-1,2,3-triazole-4-carboxamido)propyl)piperazine-1-carboxylate To 1H-1,2,3-triazole-4-carboxylic acid (32.7 mg, 0.289 mmol) in DMF (2 ml) was added HATU (110 mg, 0.289 mmol) and DIPEA (0.050 ml, 0.289 mmol). The resulting yellow solution was stirred for 10 mins and treated with 3,5-dichlorobenzyl 4-(3-amino propyl)piperazine-1-carboxylate (step 2) (100 mg, 0.289 mmol). After stirring at ambient temperature for 4 hrs, the mixture was diluted with EtOAc (50 ml) and washed with water (2*10 ml). The organic extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in DCM and applied to a 20 g silica cartridge eluting with 10% MeOH/DCM containing 1% aqueous 880 ammonia. The product fractions were concentrated to give 3,5-dichlorobenzyl 4-(3-(1H-1,2,3-triazole-4-carboxamido)propyl) piperazine-1-carboxylate as a white foam; LCMS: Rt=0.74 mins; MS m/z 439.2 and 441.2 [M-H] for chlorine isotopes; Method 2minLowpHv01

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 1H-[1,2,3]Triazole-4-carboxylic acid, in my other articles.

Reference:
Patent; Novartis AG; Legrand, Darren Mark; Furminger, Vikki; Thomson, Christopher; Hughes, Owen Rhys; Stanley, Emily; US2014/171403; (2014); A1;,
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. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 6523-49-5

The product from step 1 (645 mg) was heated in DMF-DMA (4 ml) for 2 h. On cooling the mixture was concentrated and triturated with ether / petrol to give the formamidine as a solid (664 mg). A portion of this material (56 mg) was treated with 4- triazoryl-aniline (35 mg) in AcOH (1.5 ml) at 100 for 2 h, cooled and diluted with water (25 ml). Basified with NaOH, filtered and the solid dried to give the title compound (66 mg).1H NMR delta 10.04 (IH, s), 9.24 (IH, s), 9.13 (2H, s), 8.86 (IH5 s), 8.63 (IH, s), 8.25 (2H, m), 8.04 (2H, m), 7.89 (3H, m), 3.99 (3H, s); LC-MS rt 2.32 m/z 395 ES-.

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 4-(1,2,4-Triazol-1-yl)aniline, in my other articles.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route 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.

3A: (2S,4R)-5-(3′-Fluorobiphenyl-4-O-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid 1,2,3-Triazole-4-carboxylic acid (27.3 mg, 241 mumol) was combined with EDC (42.7 muL, 241 mumol), 4-methylmorpholine (1 eq.) and HOBt (32.6 mg, 241 mumol) in DMF (0.2 mL). The resulting mixture was stirred for 5 minutes at room temperature. A solution (2S,4R)-4-amino-5-(3′-fluorobiphenyl-4-yl)-2-hydroxymethyl-2-methylpentanoic acid (80 mg, 240 mumol) and 4-methylmorpholine (53.1 muL, 483 mumol) in DMF (0.3 mL) was added, and the resulting mixture was stirred for 15 minutes. The reaction was quenched with ACOH and the product was purified by preparative HPLC and lyophilized to yield the title compound (30 mg). MS m/z [M+H]+ calc’d for C22H23FN4O4, 427.17. found 427.2.

Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 1H-[1,2,3]Triazole-4-carboxylic acid.

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

Synthetic Route of 7411-23-6, New Advances in Chemical Research in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To a colorless solution of 3,5-dibromo-lH-l,2,4-triazole (lnt-1, 250 mg, 1.1 mmol, Eq: 1) and bromocyclobutane (179 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 H20 and extracted with EtOAc (2 x 25 mL). 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 yellow liquid (288 mg, 93 % yield). MS (ES+) m/z: 281.9 [(M+H)+].

This is the end of this tutorial post, and I hope it has helped your research about 7411-23-6!

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

Reference of 60166-43-0, 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, 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, molecular formula is C4H7N3, 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 7-bromo-5-nitroisoquinolin-1(2H)-one (2b, 4.00 g, 14.9 mmol), 1,4- dimethyl-1H-1,2,3-triazole (2.17 g, 22.3 mmol), palladium acetate (334 mg, 1.49 mmol), CatacXiumA (butyl di-1-adamantylphosphine) (1.10 g, 2.97 mmol), and potassiumacetate (7.30 g, 74.3 mmol) in 2-methyl-2-butanol (100 mL) was degassed with nitrogen, and heated at 120 C in a sealed tube overnight. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (300 mL) and water (300 mL). The organic phase was separated, washed with brine (300 mL), dried over sodium sulfate, concentrated to dryness, and purified by silica gel chromatography(eluting with a gradient of 0%-i 0% methanol in ethyl acetate), affording 7-(i 4-dimethyl- iH-i,2,3-triazol-5-yl)-5-nitroisoquinolin-i(2H)-one (2c, 2.55 g, 60%) as a solid. 1H NMR (400 MHz, DMSO-d6) oe 11.95 (br. s., 1 H), 8.57 (5, 2H), 7.55 (d, J=5.38 Hz, 1 H), 6.98 (d, J=7.34 Hz, iH), 4.00 (5, 3H), 2.29 (5, 3H). MS: 284 [M-i].

I am very proud of our efforts over the past few months and hope to 1,4-Dimethyl-1H-1,2,3-triazole help many people in the next few years.

Reference:
Patent; PFIZER INC.; KUMPF, Robert Arnold; KUNG, Pei-Pei; SUTTON, Scott Channing; WYTHES, Martin James; (138 pag.)WO2015/193768; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 956317-36-5, 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. 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

(S)-(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)(5-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)-6-azaspiro[2.5]octan-6-yl)methanone 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (1 eq; prepared according to WO 2008147518), HOBT (1 eq) and EDCI.HCl (1.5 eq) dissolved in dichloromethane (5 ml/mmol) were stirred at 25 C. for 0.5-2 hours, then intermediate 2 (1 eq) dissolved in dichloromethane was added. After 18 hours the mixture was poured in an aqueous saturated solution of NaHCO3 and extracted with dichloromethane. The crude was purified by silica gel column chromatography (DCM to DCM/MeOH=9/1) to obtain the title compound with yield of 52%. 1HNMR (CDCl3) delta ppm 8.22-8.38 (m, 1H), 7.94-8.14 (m, 1H), 7.79-7.86 (m, 1H), 7.69 (m, 1H), 7.50-7.62 (m, 1H), 7.28-7.37 (m, 1H), 7.0-7.24 (m, 1H), 6.48-6.66 (m, 1H), 5.20 (m, 1H), 4.34-4.84 (m, 1H), 3.89-4.0 (m, 1H), 3.65-3.75 (m, 1H), 3.21-3.44 (m, 2H), 3.01-3.11 (m, 1H), 2.26-2.46 (m, 3H), 1.89-2.17 (m, 1H), 1.02-1.28 (m, 1H), 0.19-0.63 (m, 4H) MS=ESI+m/z 439 [M+H]+

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

Reference:
Patent; ROTTAPHARM S.P.A.; Stasi, Luigi Piero; Rovati, Lucio; US2013/310400; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 41253-21-8, New Advances in Chemical Research in 2021. The appropriate choice of redox mediator can avoid electrode passivation and overpotential, which strongly inhibit the efficient activation of substrates in electrolysis. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

2-(1H-1,2,4-Triazol-1-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 C. 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) delta ppm: 8.74 (1H, s), 8.16 (1H, s), 7.82 (1H, dd, J=4.9, 1.3 Hz), 7.77-7.25 (2H, m), 7.57-7.51 (1H, m). LCMS [M+H]+ calcd for C9H7N4: 171.06. found: 171.12

I am very proud of our efforts over the past few months and hope to Sodium 1,2,4-triazol-1-ide help many people in the next few years.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1001401-62-2, 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. 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.

A mixture of A-1 (0.72 g, 3.8 mmol) and thionyl chloride (0.36 mL, 5.0 mmol) in toluene (7 mL) and a drop of DMF is heated to 60C for 2h, then cooled and concentrated. The residue is dissolved in 5 mL of dry DCM and added dropwise to a stirred mixture of C-1 (0.65 g, 4.64 mmol) and TEA (1 .44 mL, 10.3 mmol) in dry DCM (10 mL) at OC. The reaction is stirred at RT for 2h. Water is added and the organic layer is separated, washed with citric acid (10% aq. solution) and with NaHC03 (sat. aq. solution). The organic layer is dried and concentrated to provide 0.94 g of C-3. ESI-MS: 275.1 [M+H]+, HPLC (Rt): 0.69 min (method M)

The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.I hope my blog about 2-(2H-1,2,3-Triazol-2-yl)benzoic acid is helpful to your research.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; (70 pag.)WO2017/178338; (2017); A1;,
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. 288-88-0, name is 1H-1,2,4-Triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

General procedure: A mixture of CuI (0.10 g, 0.50 mmol), the required azole(10 mmol), K3PO4 (4.4 g, 20 mmol), the required halide (12 mmol)and N,N0-dimethylethylenediamine (0.11 mL, 1.0 mmol) in DMF(5 mL) was degased and heated under argon at 110 C for 72 h.After filtration over celite (washing using AcOEt) and removal ofthe solvents, the crude product is purified by chromatography oversilica gel (the eluent is given in the product description). 4.3.1 1-Phenyl-1H-1,2,4-triazole (2a) Compound 2a was prepared from 1,2,4-triazole (0.69 g) and iodobenzene (1.4 mL) using the general procedure 1, and was isolated (eluent: heptane/AcOEt 7:3) in 96% yield as a yellow powder: mp 48 C (lit. 28 46 C); 1H NMR (CDCl3, 300 MHz) 7.42 (m, 1H), 7.53 (m, 2H), 7.71 (m, 2H), 8.15 (s, 1H), 8.74 (s, 1H); 13C NMR (CDCl3, 75 MHz) 120.1 (2CH), 128.3 (CH), 129.9 (2CH), 137.1 (C), 140.9 (CH), 152.7 (CH).

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 1H-1,2,4-Triazole, in my other articles.

Reference:
Article; Nagaradja, Elisabeth; Bentabed-Ababsa, Ghenia; Scalabrini, Mathieu; Chevallier, Floris; Philippot, Stephanie; Fontanay, Stephane; Duval, Raphael E.; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Roisnel, Thierry; Mongin, Florence; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6355 – 6363;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics