Triazoles

Some common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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. 41253-21-8

To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added the sodium salt of 1,2,4-triazole (6.3 g, 70 mmol) and the mixture was stirred at 90 C. for 3 h, filtered and concentrated. The residue was adsorbed onto Silica gel and purified by flash chromatography eluting with 0%-10%-30% ethylacetate/hexanes to give 4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile as colorless needles (2.46 g, 18%) and 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitril as a white solid (0.746 g, 6%). 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile. Colorless needles (2.46 g, 18% yield) 1H NMR (500 MHz, CDCl3) delta 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13. 4-(1H-1,2,4-Triazol-1-yl)-2-fluorobenzonitrile. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) delta 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41253-21-8, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, 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.

A suspension of 6-bromo-3-chloroisoquinoline (60 mg, 0.25 mmol), 1 -methyl- 1 H-1 ,2,3-triazole (41 mg, 0.50 mmol), Pd(OAc)2 (2.22 mg, 9.9 umol) and KOAc (49 mg, 0.50 mmol) in DMA (4 mL) was stirred at 150^ under microwave irradiation for 60 minutes. The reaction mixture was diluted with brine and extracted with EtOAc. The combined organic layers were washed with water and dried with Na2S04 and concentrated in vacuo. The residue was purified using Biotage silica gel column chromatography eluting with 40% EtOAc in cyclohexane to afford the title compound as a white solid (19 mg, 31 %). 1 H NMR (500 MHz, CDCI3) : delta .17 (t, J = 0.9 Hz, 1 H), 8.15 (dt, J = 8.5, 0.9 Hz, 1 H), 7.94 – 7.85 (m, 2H), 7.82 (d, J = 1 .1 Hz, 1 H), 7.67 (dd, J = 8.5, 1 .6 Hz, 1 H), 4.19 (s, 3H). LCMS (ESI) Rt = 2.00 minutes MS m/z 245 [M+H]+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16681-65-5.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; CHEUNG, Jack; ATRASH, Butrus; SHELDRAKE, Peter; WO2014/37751; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common heterocyclic compound, 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, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 956317-36-5.

To a stirred solution of 7(184 mg,0.86 mmol) in DMF (5 ml) was added 92) (174 mg, 0.86 mmol), EDCI (198 mg, 1.03 mmol), HOAt (140 mg, 1.03 mmol), and N-methylmorpholine(0.5 ml, 4.30 mmol), the resulting mixture was stirred for 16 h at room temperature. The reaction mixture was diluted with EtOAc, sat.NaHCO3 aq, and organic phase was separated, the aqueous mixture was extracted with EtOAc. The organic phase and extracts were combined, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on SiO2(Hexane- EtOAc = 2 : 1) to give 8 (300mg,87%) as a colorless oil. The 1H NMR and 13C NMR data for this compound was extremely complicated due to its existence as rotamers.1H NMR (500 MHz, CDCl3):delta 7.92-7.75 (3H, m), 7.33-7.10 (2H, m), 4.87-2.90 (7H, m), 2.41 (3H, s),2.19-1.88 (1H, m), 1.71-1.37 (10H, m), 1.31-1.10 (3H, m); 13C NMR(125 MHz, CDCl3): delta 169.59, 169.43, 168.98, 168.76, 154.89, 154.69,154.44, 138.16, 138.11, 137.81, 135.36, 135.24, 133.65, 133.57, 133.30, 130.12,129.52, 129.44, 129.03, 128.93, 128.27, 128.11, 127.95, 122.22, 122.13, 121.90,121.83, 79.54, 79.39, 52.02, 51.30, 48.16, 47.53, 46.39, 46.16, 45.49, 45.10,44.76, 44.41, 43.40, 42.96, 42.43, 42.03, 41.53, 41.16, 39.44, 36.85, 36.40,35.81, 35.02, 34.76, 34.47, 33.89, 29.40, 28.24, 28.16, 20.73, 20.67, 19.76,19.5517.96, 17.57, 17.33, 16.67; IR (neat): 1683, 1635 cm-1; MS (EI)m/z 399 (M+);HRMS (EI) calcd for C21H29N5O3:399.2270 (M+), found: 399.2273; [alpha]17 D -34.9 (c0.9, CHCl3).

The synthetic route of 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Minehira, Daisuke; Takahara, Satoyuki; Adachi, Isao; Toyooka, Naoki; Tetrahedron Letters; vol. 55; 42; (2014); p. 5778 – 5780;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, A common compound: 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: In a 10 mL round-bottomed flask, (2S,4R)-4-(2-chloro-4-fluorophenylsulfonyl)-N-(1- cyanocyclopropyl)- 1- (1- (trifluoromethyl)cyclopropanecarbonyl)pyffolidine-2-carboxamide (example 8b)) (400 mg, 788 imol, Eq: 1.00) was combined with DMA (5 mL) to give a colorless solution. 1H-1,2,4-triazole (111 mg, 1.58 mmol, Eq: 2.00) and cesium carbonate (513 mg, 1.58 mmol, Eq: 2.00) were added. The reaction mixture was heated to 80 C and stilTed for 3h. The reaction mixture was poured into water and extracted with EtOAc (2x). The organic layers were combined, washed with saturated aqueous NaHCO3 solution (lx),water (3x) and brine (lx). The organic layers were dried over Na2SO4 and concentrated in vacuo.The crude material was purified twice by flash chromatography (silica gel, 20g, DCM/MeOH 98/2, 19/1) and (silica gel, 20g, Heptan/AcOEt 1/2, 1/3, 1/4) to yield the title compound as a white foam (264 mg; 60%).: _Example 11 was obtained as a byproduct during the synthesis of example 10 as a white solid (34 mg; 7%).

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-Methyl-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.; HAAP, Wolfgang; KUHN, Bernd; LUEBBERS, Thomas; PETERS, Jens-Uwe; (93 pag.)WO2017/144483; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, 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. 7170-01-6

EXAMPLE 103 [4-(3-Methyl-1,2,4-triazol-1yl)-2-trifluoromethyl-phenyl](5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone To a suspension of 60% sodium hydride in oil (0.3 g) in dimethylformamide (50 ml) was added dropwise 3-methyl-12,4-triazole (0.45 g).. After hydrogen gas evolution ceased, 4-fluoro-2-trifluoromethyl-phenyl-(5H,11H-pyrrolo[2,1-c][1,4]-benzodiazepine-10-yl)-methanone (1.76 g) was added and the reaction mixture was heated in a sand bath at 110 C for 18 hours.. The mixture was poured onto ice, diluted with brine, and extracted with dichloromethane.. The combined extracts were dried over anhydrous sodium sulfate and filtered through a short column of anhydrous sodium magnesium silicate.. The solution was concentrated in vacuo and the residue was triturated with diethyl ether to give 0.81 g of the title compound as colorless crystals, m.p. 148-150 C, MS m/z: 438.2 (M+H)+, 875.8 (2M+H)+.

Statistics shows that 7170-01-6 is playing an increasingly important role. we look forward to future research findings about 3-Methyl-1H-1,2,4-triazole.

Reference:
Patent; Wyeth; EP1000062; (2004); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, Adding a certain compound to certain chemical reactions, such as: 7170-01-6, name is 3-Methyl-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 7170-01-6.

41. 5-(3-Methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2-(1H)-one A stirred mixture containing 13.5 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 20 g of 3-methyl-1H-1,2,4-triazole and 75 ml of N-methylpyrrolidinone was heated in an oil bath at 170-180 C. for 18 hours and then cooled to room temperature whereupon a tan solid crystallized out. The mixture was diluted by adding 125 ml of water and the separated solid was collected, washed with water, air-dried and combined with another 1.2 g sample of the same material obtained in another run starting with 2.25 g of 5-bromo-1,6-naphthyridin-2(1H)-one. The combined solids were recrystallized from dimethylformamide and dried in an oven at 95-100 C. for three days to yield 6.1 g of 5-(3-methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. >300 C.

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

Reference:
Patent; Sterling Drug Inc.; US4657915; (1987); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, name is 1H-1,2,3-Triazole, 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. 288-36-8

To a solution of 3-chloro-4-fluoronitrobenzene (1.2 g, 6.836 mmol) and 2H-1,2,3-triazole (0.567 g, 8.203 mmol) in anhydrous DMA (5 mL) was added K2CO3 (1.89 g, 13.7 mmol). The reaction mixture was stirred at 55 C. overnight. The reaction was concentrated to give a crude oil. The crude product was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate from 100/0 to 20/80) to give compound 4d (1 g, 65.1%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.88-8.02 (m, 3H), 8.28 (dd, J=8.93, 2.54 Hz, 1H), 8.49 (d, J=2.21 Hz, 1H).

Statistics shows that 288-36-8 is playing an increasingly important role. we look forward to future research findings about 1H-1,2,3-Triazole.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 3641-08-5, name is 2H-1,2,4-Triazole-3-carboxamide, 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 3641-08-5. 3641-08-5

A stirred mixture of 1H-1,2,4-triazole-3-carboxamide (500 mg, 4.46 mmol) in 1,2-dichloroethane (4.46 mL) treated at room temperature with 2,6-lutidine (2.08 mL, 17.84 mmol) and triethylsilyl trifluoromethanesulfonate (3.03 mL, 13.38 mmol) and heated under a nitrogen atmosphere at 50C. After 4 hours of heating the reaction solution allowed to cool to room temperature and diluted with dichloromethane (25 mL), washed with water (25 mL), 0.5M hydrochloric acid (25 mL), water (25 mL), dried over MgSO4, filtered, and evaporated to solid. The solid was flash chromatographed (silica gel, 10-65% ethyl acetate:hexane) to give the product as a white solid (683 mg).1H NMR (CDCl3, 500MHz, ppm) 0.89 (q, J=8Hz, 6H, CH2), 1.03 (t, J=8 Hz, 9H, CH3), 6.77 (s, 1H, NH), 8.63 (s, 1H, triazole H-5).LC/MS m/z (positive ion scan) M+l= 227.20.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2H-1,2,4-Triazole-3-carboxamide.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SCYNEXIS, INC.; GREENLEE, Mark, L.; WILKENING, Robert; APGAR, James; SPERBECK, Donald; WILDONGER, Kenneth, James; MENG, Dongfang; PARKER, Dann, L.; PACOFSKY, Gregory, James; HEASLEY, Brian, Haid; MAMAI, Ahmed; NELSON, Kingsley; WO2010/19204; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, I believe this compound will play a more active role in future production and life. 41253-21-8

Example 4 Selectivity in the Preparation of Intermediate III The procedure of Example 3 was repeated with various solvents and bases, and the reaction mixtures were analyzed using HPLC to determine the ratio of intermediate III to isomer IV impurity. Solvents used were acetonitrile (ACN), chloroform (CHCl3), dimethylformamide (DMF), dichloromethane (CH2Cl2), acetone, CH(OC2H5)2, N-methyl-2-pyrrolidone (MP), dimethylacetamide (DMA), methanol, water, toluene, and mixtures thereof. Bases used were sodium iodide (NaI), potassium t-butoxide (KOtB), potassium hydroxide (KOH), potassium carbonate (K2CO3), potassium iodide (KI), commercial sodium triazolate (NAT), tetrabutyl ammonium hydroxide (TBAI), and mixtures thereof. The results are summarized in Table 1 below, in which the units of dilution are parts by weight of solvent based on the weight of the 4-(bromomethyl)benzonitrile. As illustrated in Table 1, choice of solvent has the largest effect on the resulting ratio of intermediate III to isomer IV impurity. Choice of base, dilution, and reaction times/temperatures also affect the ratio of intermediate III to isomer IV impurity, but to a lesser degree. Dimethylacetamide solvent showed the most selectivity for intermediate III, followed by methylpyrrolidone.

The chemical industry reduces the impact on the environment during synthesis 41253-21-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MacDonald, Peter Lindsay; Bigatti, Ettore; Rossetto, Pierluigi; Harel, Zvi; US2007/66831; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7411-23-6, A common compound: 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Into a 250-mL round-bottom flask, was placed 3,5-dibromo-lH-l,2,4-triazole (5 g, 22.04 mmol, 1.00 equiv) in N,N-dimethylformamide (25 mL) and potassium carbonate (9 g, 65.12 mmol, 3.00 equiv). This was followed by the addition of SEMC1 (4.43 g, 26.53 mmol, 1.20 equiv) dropwise with stirring at 0 C. The resulting mixture was stirred overnight at 25 C. The resulting solution was diluted with 100 mL of EA, washed with 5 x 100 mL of saturated brine and concentrated. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1/10). This resulted in 7.26 g (92%) of 3,5-dibromo-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-l,2,4-triazole as yellow oil. MS (ES, m/z) [M+H]+: 356, 358, 360.

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; THE ROCKEFELLER UNIVERSITY; BRESLOW, Jan L.; PONDA, Manish P.; SELNICK, Harold; EGBERTSON, Melissa; (61 pag.)WO2017/123518; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics