Category: Triazoles

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. 64922-04-9, name is Ethyl 1H-1,2,4-triazole-5-carboxylate belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C5H7N3O2

A solution of 613 mg (14.0 mmol) of sodium hydride in 10 ml of 1-methyl-2-pyrrolidinone is cooled to 0 – 5C and treated dropwise with a solution of 1.74 g (12.4 mmol) of 1H-[1,2,4]triazole-3-carboxylic acid ethyl ester in 10 ml of 1-methyl-2-pyrrolidinone over 8 minutes. The mixture is stirred for 1 hour at 0 – 5C and a solution of 3.00 g (11.2 mmol) of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester in 10 ml of 1-methyl-2-pyrrolidinone is added. The mixture is allowed to warm slowly to room temperature and stirred for 18 hours under N2. It is poured into water and extracted with ethyl acetate. The organic phase is separated and dried over NaaSO^ filtered and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, hexane / ethyl acetate 1:1) and the mixed fractions are recrystallized in toluene to provide overall 3.12 g (71 %) of 1-(5-methoxycarbonyl-4-nitro-2-trifluoromethyl-phenyl)-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester, m.p. 190 – 192C.

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Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/10591; (2006); A2;,
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. 288-36-8, name is 1H-1,2,3-Triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 288-36-8

EXAMPLE B2-(2H-l,2.3-triazol-2-v0benzoic acid (B- 1)A solution of 2-iodobenzoic acid (3.0 g, 12.09 mmol) in DMF was treated with (1.5 g, 21.7 mmol) 1,2,3-triazole, 7.08 g (21.7 mmol) CsCO3, 1 14 mg (0.60 mmol) CuI and 310 mg (2.17 mmol) trans-N,N’-dimethylcyclohexane-l,2-diamine. The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to rt, diluted with EtOAc, and filtered through Celite. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting desired 2-(2H-l,2,3-triazol-2-yl)benzoyl acid, B-I . Data for IM : 1HNMR (500 MHz, DMSO-(I6) delta 13.05 (br s , IH), 8.12 (s, 2H), 7.81-7.52 (m, 4H) ppm. The undesired 2-(lH-l,2,3-triazol-2-yl)benzoic acid (B-2) eluted second.

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Reference:
Patent; MERCK & CO., INC.; WO2008/143856; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-65-5, 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

l-Methyl-5-tributylstannanyl-lH-[l,2,3]triazole; To a solution of 1 -methyl- lH-[l,2,3]triazole (1.33 g, 16 mmol) in THF (20 mL) at -78 0C, was added dropwise n-BuLi (11 mL,1.6M, 18 mmol). The mixture was stirred at -78 0C for 2 h before addition of Bu3SnCl (4.75 mL, 17.6 mmol). The mixture was stirred at this temperature for 1 h and at r.t. for 1 h. The mixture was concentrated in vacuo and hexanes was added. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo to afford l-methyl-5-tributylstannanyl-lH- [l,2,33triazole (6.12 g, 82% yield) as a yellow syrup.

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 1-Methyl-1H-1,2,3-triazole.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/108591; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 135242-93-2, 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, 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 solution of 0.5 g (4.42 mmol, 1.0 eq.) of (l-methyl-li/-l,2,4-triazol-3-yl)methanol (Xlla) in 20 mL of acetonitrile was added 1.07 g (6.63 mmol, 1.5 eq.) of I,G -carbonyl and the mixture was stirred at room temperature for 2 h. Volatiles were removed in vacuo and the residue was resuspend in 20 mL of water. The mixture was extracted with 3 x 50 mL of 5% methanol in methylene chloride. The combined organic extracts were washed with 50 mL of sat. sodium carbonate solution, followed by 50 mL of brine, dried (T^SCL), filtered and the solvent was removed in vacuo to provide 0.77 g of ( 1 -methyl- 1 H- 1 2.4-triazol-3-yl)methyl 1 //-imidazole- 1 -carboxy late (XIHa).

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 (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol is helpful to your research.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; KULTGEN, Steven; COLE, Andrew G.; (217 pag.)WO2020/23710; (2020); A1;,
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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 7170-01-6

To a vial charged with racemic 5-(benzofuran-2-yl)-3 – (5-bromo-6-methoxypyridin-2-yl)-5,6-dthydro-4H- 1 ,2,4-oxadiazine (110 mg, 0.28 mmol, 1.0 equiv.), 3-methyl-1H-1,2,4-triazole (47.1 mg, 0.57 mmol, 2.0 equiv.), and K3P04 (120 mg, 0.57 mmol, 2.0 equiv.) under N2 atmosphere was added degassed 4:1 PhMe:dioxane solvent mixture (2.00 mL). To a second vial charged with Pd2(dba)3 (20.8 mg, 0.02 mmol, 8.0 mol%) and Me4-di-t-BuXPhos (CAS 857356-94-6, 21.8 mg, 0.05 mmol, 16 mol%) under N2 atmosphere was added degassed 4:1 PhMe:dioxane solvent mixture (0.83 mL). This mixture was stirred for 3 minutes at 120 C to provide a dark red solution which was cooled to RT and transferred to the first vial. The reaction was degassed by bubbling with N2 for 5 minutes and then sealed. The reaction mixture was stirred at 120 C for 16 h. The reaction was cooled to RT and filtered through a pad of celite which was washed thoroughly with EtOAc. The filtrate was concentrated, and the residue was purified by normal phase chromatography on silica (0-5% MeOH / DCM) to afford 5-(Benzofuran-2-yl)-3-(6-methoxy-5-(3-methyl-1H- 1,2,4-triazol-1-yl)pyridin-2-yl)-5,6-dthydro-4H-1,2,4-oxadiazine (77.4 mg, 70%) as an off- white solid.

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Reference:
Patent; FORUM PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 584-13-4, name is 4H-1,2,4-Triazol-4-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. name: 4H-1,2,4-Triazol-4-amine

5-(4H-l,2,4-TriazoI-4-ylamino)-4l-methoxybiphenyl-2-carbonitrile (CAB06046) To a solution of 4No.-l ,2,4-triazol-4-amine (3.441 g, 40.928 mmol) in DMSO (40 mL) was added KOtBu (4.593 g, 40.928 mmol). The mixture was stirred for 0.5 hours at room temperature before CAB06042 (4.65 g, 20.468 mmol) was added and stirring was continued for 1 hour. The mixture was poured into crushed ice and neutralized with 2M KHSO4 solution. The precipitate was filtered off and recrystallised from acetone/Et2theta to afford CAB06046 (5.07 g, 85%) as a light yellow crystalline solid. Mp, 176-177 0C; 1H NMR (400 MHz5 OMSO-d6) delta 3.81 (s, 3H)5 6.47 (d, J = 2.4 Hz5 IH)5 6.54 (dd, J = 8.6, 2.4 Hz, IH)3 7.07 (AA5BB’, 2H)5 7.43 (AA’BB 2H), 777 (J = 8.6 Hz, IH), 8.86 (s5 2H), 10.28 (s5 IH); 13C NMR (100.6 MHz, DMSO-^) delta 55.3, 101.2, H LO, 1123, 114.2, 119,1, 129.7, 130.0, 135.6, 144.1, 146.1, 150.8, 159 8; LRMS (ES+): m/z 292.3 (100%, [IvH-H]+); HRMS (ES+) calcd for C16Hj4N5O [M+H]+: 292,1193, found 292.1180; Anal. Calcd for C16Hi3N5O: C, 65.97; H5 4.50; N5 24.04. Found C, 65.9; H5 4,56; N5 23.8.

The catalyzed pathway has a lower Ea, but the net change in energy that results from the reaction is not affected by the presence of a catalyst. In my other articles, you can also check out more blogs about 584-13-4

Reference:
Patent; STERIX LIMITED; WOO, Lok Wai Lawrence; BUBERT, Christian; WOOD, Paul Michael; PUTEY, Aurelien; PUROHIT, Atul; POTTER, Barry Victor Lloyd; WO2011/23989; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 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. Quality Control of 1H-[1,2,3]Triazole-4-carboxylic acid

Example 16 (R)-5-(5?-Chloro-2?-fluorobiphenyl-4-yl)-2-(2-hydroxyethyl)-2-hydroxymethyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid (isomers a and b) [0438] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)-propyl]-3-hydroxymethyl-dihydro-furan-2-one (isomer a; 10 mg, 30 mumol, 1.0 eq.) and DIPEA (30 muL, 170 mumol, 5.6 eq.) were dissolved in DMF (200 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 90 mumol, 3.0 eq.), DIPEA (60 muL, 340 mumol, 11.2 eq.) and HATU (15 mg, 40 mumol, 1.3 eq.), were dissolved in DMF (600 muL) and stirred at room temperature for a few minutes. The solutions were then combined and the resulting mixture stirred at room temperature and when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture, the organics were then separated and concentrated in vacuo. The crude residue was dissolved in a 1:1 solution of MeOH and aqueous 2N NaOH (4 mL), and stirred at room temperature for 30 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; 3 mg). LCMS (ESI): calc. C23H24ClFN4O5=490; obs. M+H=491.2. Retention time: 2.04 min. [0440] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)-propyl]-3-hydroxymethyl-dihydro-furan-2-one (isomer b; 30 mg, 52 mumol, 1.0 eq.) and DIPEA (50 muL, 291 mumol, 5.6 eq.) were dissolved in DMF (200 muL). 1H-1,2,3-triazole-4-carboxylic acid (17 mg, 156 mumol, 3.0 eq.), DIPEA (100 muL, 582 mumol, 11.2 equiv.) and HATU (25 mg, 68 mumol, 1.3 eq.), were dissolved in DMF (600 muL) and stirred at room temperature for a few minutes. The solutions were then combined and the resulting mixture was stirred at room temperature; when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture. The organic layer was separated, concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer b; 3.9 mg). LCMS (ESI): calc. C23H24ClFN4O5=490; obs. M+H=491.2. Retention time: 1.99 min. [0441] 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 3.6 minutes, then 100% B for 1.0 minute, detection at 254 nm

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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.; US2015/209352; (2015); 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. 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. Recommanded Product: 4-Phenyl-1,2,4-triazolidine-3,5-dione

General procedure: A mixture of dimedone (1 mmol), aldehyde or isatin (1 mmol) and 4-phenylurazole (1 mmol), and catalyst (0.01 g, 5 mol%) in water (5 mL) was refluxed. After completion of the reaction that was monitored by TLC (EtOAc:n-hexane, 1:3), the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with water and cooled with ethanol to afford the pure product.

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Reference:
Article; Seyyedhamzeh, Mozhdeh; Shaabani, Shabnam; Hamidzad Sangachin, Mona; Shaabani, Ahmad; Research on Chemical Intermediates; vol. 42; 4; (2016); p. 2845 – 2855;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 1186050-58-7, 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, 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C9H6FN3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Example 102 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide To a solution of (1S,2S)-1-N-[5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 1; 1.09 g, 3.87 mmol) in DCM (13 ml) was added 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1186050-58-7; 0.802 g, 3.87 mmol), DIPEA (2.027 ml, 11.61 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (0.579 g, 4.26 mmol) and EDC (0.816 g, 4.26 mmol). The reaction was stirred at room temperature for 17 hours and was then partitioned between DCM and a saturated solution of sodium bicarbonate, filtered through a hydrophobic fit and concentrated in vacuo. The residue was purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol) and re-crystallised from IPA to afford the title compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.41-1.59 (m, 2H), 1.59-1.76 (m, 2H), 1.95-2.10 (m, 2H), 4.06-4.20 (m, 2H), 6.68 (d, J=8.8 Hz, 1H), 7.29-7.41 (m, 2H), 7.57-7.66 (m, 2H), 7.71-7.75 (m, 1H), 8.00 (s, 2H), 8.25-8.28 (m, 1H), 8.63 (d, J=6.8 Hz, 1H) MS ES+: 435

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-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid is helpful to your research.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, New Advances in Chemical Research in 2021.In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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 methyl 5-chloro-6-methoxy-3-[(4-methyl-l-naphthoyl)amino]pyrazine-2- carboxylate prepared in Example 25E (0.258 g, 0.67 mmol, 1 eq.), JV-bromosuccinimide (0.123 g, 0.69 mmol, 1.0 eq.) and benzoyl peroxide (0.018 g, 0.07 mmol, 0.11 eq.) in 100 mL carbon tetrachloride was refluxed for 1 h until LC/MS showed that bromination was complete. The reaction mixture was cooled to 50 0C and 1,2,3-triazole (0.245 g, 3.55 mmol, 5.3 eq.) was added. The resulting mixture was stirred at 80 0C for 2 h until LC/MS showed that the reaction was complete. The solvents were removed in vacuo. The residue was dissolved in 10 mL dimethyl sulfoxide. The resulting dimethyl sulfoxide solution was purified by reversed-phase preparative HPLC. Freeze drying gave 0.062 g (21 %) of title compound.1H NMR (400 MHz, DMSO-*) delta (ppm) 3.80 (s, 3H), 4.01 (s, 3H), 5.72 (s, IH), 6.16 (s, 2H), 7.37 (d, J=7.2 Hz, IH), 7.63 (m, 2H), 7.71 (d, J=7.3 Hz, IH), 7.73 (s, IH), 8.18 (s, IH), 8.26 (m, 2H), 11.41 (br s, IH).

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Reference:
Patent; ASTRAZENECA AB; WO2007/61360; (2007); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics