Category: 7170-01-6

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 7170-01-6 name is 3-Methyl-1H-1,2,4-triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 7170-01-6

Step A. 2-Chloro-4-(3 -methyl-i H-i ,2,4-triazol- 1 -yl)benzaldehydeTo a solution of 2-chloro-4-fluorobenzaldehyde (95 mmol, 15 g) and 3-methyl-1H-i,2,4-triazole(114 mmol, 9.4 g) in CH3CN (300 mL) was added K2C03 (142 mmol, 20 g) and stirred at 60 C.After 24 h, the reaction mixture was added water and extracted with EtOAc. The organic extracts washed with saturated aq. NaC1, dried over Na2SO4, and filtered and concentrated in vacuo. The crude was purified by column chromatography (heptane :EtOAc = 20:80-10:90) to give the title compound. MS (ESI) mlz = 222, 224 (M+H)?H NMR (300 MHz, CDC13) 5 (ppm): 10.45 (1H, s), 8.55 (1H, s), 8.06 (1H, d, J 8.6 Hz), 7.87(1H, d, J= 2.1 Hz), 7.68 (1H, dd, J 8.6, 2.1 Hz), 2.51 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyl-1H-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SAKURADA, Isao; HIRABAYASHI, Tomokazu; MAEDA, Yoshitaka; NAGASUE, Hiroshi; MIZUNO, Takashi; XU, Jiayi; ZHANG, Ting; SMITH, Cameron; PARKER, Dann; WO2015/160636; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, molecular formula is C3H5N3, 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. 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7170-01-6, its application will become more common.

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

The chemical industry reduces the impact on the environment during synthesis 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life. 7170-01-6

Example 4 Synthesis of SC11 To a stirred solution of benzoic acid (116 mg, 0.94 mmol) in DCM (3 mL) were added compound 7 (200 mg, 0.94 mmol), TEA (0.4 mL, 2.82 mmol) and HBTU (536 mg, 1.39 mmol). The resulting mixture was stirred at r.t. overnight before quenched with sat. NaHCO3. The layers were separated and the aqueous layer was extracted with DCM (10 mL*3). The combined organic layers was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 0?50% ethyl acetate in petroleum ether with 0.5% TEA) to provide compound 8 (164 mg, 55%) as a yellow solid. Compound 9 (303 mg, 100%) was obtained as a yellow oil by treating compound 8 (345 mg, 1.09 mmol) with 4N HCl/Dioxane (3 mL). To a solution of compound 12 (0.8 g; 4.5 mmol) in N-methylpyrrolidone (5 ml), water (0.5 ml) and hydrochloric acid (5-6 drops) were added. The mixture was stirred at 100 C. for 6 h. The mixture was cooled to room temperature and water (100 ml) was added. Then NaHCO3 sat. (20 ml) was added, the product was extracted with EtOAc (5*20 ml). Combined extracts were dried over Na2SO4 and concentrated to afford compound 13 (0.6 g, 81%) as pink solid. A solution of compound 13 (1.8 g; 11 mmol) in POCl3 (20 ml) was stirred at 100 C. for 12 h. Then POCl3 was evaporated under reduced pressure. To a residue ice water (100 ml) and then NaHCO3 sat. (25 ml) were added, the product was extracted with EtOAc (3*35 ml). Combined extracts were dried over Na2SO4 and concentrated to afford compound 14 (0.8 g, 40%) as light-yellow solid At 143 C., to molten 3-methyl-1H-1,2,4-triazole (744 mg, 8.95 mmol) under N2 atmosphere, was added compound 14 (392 mg, 1.79 mmol). After stirring for 20 hrs, the reaction mixture was cooled down to r.t. and partitioned between H2O (20 mL) and EA (20 mL). The layers were separated and the aqueous layer was extracted with EA (20 mL*3). The combined organic layers was dried over Na2SO4, filtered and concentrated. The residue was purified by prep. HPLC (C18, 10% to 89% acetonitrile in water (0.1% formic acid)) to compound 19 (182 mg, 44%) as a white solid. To a stirred solution of AlCl3 (1.588 g, 11.9 mmol) in DCM (10 mL) was added methyl 2-chloro-2-oxoacetate (389 mg, 3.18 mmol) and the resulting mixture was stirred at r.t. until it became a clear solution before introduction of compound 19 (182 mg, 0.79 mmol, in 1 mL DCM). The stirring was continued at r.t. overnight. After completion of the reaction, the mixture was quenched with sat. NaHCO3 and extracted with DCM (10 mL*3). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (silica gel, 0?90% ethyl acetate in petroleum ether) to provide compound 20 (58 mg, 23%) as a yellow oil. To a stirred solution of compound 20 (58 mg, 0.18 mmol) in MeOH/H2O (1 mL/2 mL) was added NaOH (15 mg, 0.37 mmol). After stirring at r.t. for 15 min, the reaction mixture was neutralized with 1N HCl, concentrated and lyophilized to provide compound 21 (73 mg, 95%, mixed with NaCl) as a green solid. Compound 21 (55 mg, 0.18 mmol) in DMF and compound 9 (59 mg, 0.27 mmol) were added to DIPEA (0.28 mL, 1.63 mmol) and DEPBT (325 mg, 1.09 mmol). After stirring at r.t. overnight, the reaction mixture was concentrated to remove DMF under the reduced pressure. The residue was partitioned between with EA (10 mL) and sat. NaHCO3 (10 mL). The layers were separated and the aqueous layer was extracted with EA (10 mL*2). The combined organic layers was dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative HPLC to give compound SC11 (22 mg, 24%).

The chemical industry reduces the impact on the environment during synthesis 7170-01-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Drexel University; Cocklin, Simon; (79 pag.)US2016/214998; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, 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. 7170-01-6

A mixture of compound precursor 5b (150 mg, 0.35 mmol), 3-methyl-1,2,4-triazole (581 mg, 7 mmol; 20 eq.; prepared by the method described in Coll. Czech. Chem. Comm. 1985, 49, 2492), copper powder (45 mg, 0.7 mmol; 2 eq.), potassium carbonate (97 mg, 0.7 mmol; 2 eq.) was flushed with anhydrous nitrogen and heated in a sealed tube at 160 C. for 11 h. Upon cooling, to the mixture was added MeOH, and the insoluble material was filtered. The filtrate was concentrated in vacuo and purified by C-18 reverse phase column (Prep. System eluting with MeOH-water containing 0.1% TFA) to obtain 19 mg (0.040 mmol, Y. 11%) of the title compound Example 216 as amorphous powder (TFA salt): MS m/e 474 (MH); 1H NMR (DMSO-d6) delta ppm 2.50 (3H, s, overlapped with DMSO peaks), 3.44 (4H, br, CH2N), 3.68 (4H, br, CH2N), 4.00 (3H, s, CH3O), 7.46 (5H, br. s, Ar-Hs), 7.89 (1H, s), 8.25 (1H, s), 9.24 (1H, s), 12.41 (1H, s, NH).

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 3-Methyl-1H-1,2,4-triazole.

Reference:
Patent; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; Kadow, John F.; Yin, Zhiwei; Xue, Qiufen May; Regueiro-Ren, Alicia; Matiskella, John D.; Ueda, Yasutsugu; US2004/110785; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of compound 12 (0.8 g; 4.5 mmol) in N-methylpyrrolidone (5 ml), water (0.5 ml) and hydrochloric acid (5-6 drops) were added. The mixture was stirred at 100C for 6 h. The mixture was cooled to room temperature and water (100 ml) was added. Then NaHCO3 sat. (20 ml) was added, the product was extracted with EtOAc (5¡Á20 ml). Combined extracts were dried over Na2SO4 and concentrated to afford compound 13 (0.6 g, 81%) as pink solid. A solution of compound 13 (1.8 g; 11 mmol) in POCl3 (20 ml) was stirred at 100 C for 12 h. Then POCl3 was evaporated under reduced pressure. To a residue ice water (100 ml) and then NaHCO3 sat. (25 ml) were added, the product was extracted with EtOAc (3¡Á35 ml). Combined extracts were dried over Na2SO4 and concentrated to afford compound 14 (0.8 g, 40%) as light-yellow solid At 143C, to a melt 3-methyl-1H-1,2,4-triazole (744 mg, 8.95 mmol) under N2 atmosphere was added compound 14 (392 mg, 1.79 mmol). After stirring for 20 hrs, the reaction mixture was cooled down to r.t. and partitioned between H2O (20 mL) and EA (20 mL). The layers were separated and the aqueous layer was extracted with EA (20 mL x 3). The combined organic layers was dried over Na2SO4, filtered and concentrated. The residue was purified by prep. HPLC (C18, 10% to 89% acetonitrile in water (0.1% formic acid)) to compound 19 (182 mg, 44 %) as a white solid. To a stirred solution of AlCl3 (1.588 g, 11.9 mmol) in DCM (10 mL) was added methyl 2-chloro-2-oxoacetate (389 mg, 3.18 mmol) and the resulting mixture was stirred at r.t. until it became a clear solution before introduction of compound 19 (182 mg, 0.79 mmol, in 1 mL DCM). The stirring was continued at r.t. overnight. After completion of the reaction, the mixture was quenched with saturated NaHCO3 and extracted with DCM (10 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (silica gel, 0 ~ 90% ethyl acetate in petroleum ether) to provide compound 20 (58 mg, 23 %) as a yellow oil. To a stirred solution of compound 20 (58 mg, 0.18 mmol) in MeOH/H2O (1 mL/2 mL) was added NaOH (15 mg, 0.37 mmol). After stirring at r.t. for 15 min, the reaction mixture was neutralized with 1N HCl, concentrated and lyophilized to provide compound 21 (73 mg, 95 %, mixed with NaCl) as a green solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Tuyishime, Marina; Danish, Matt; Princiotto, Amy; Mankowski, Marie K.; Lawrence, Rae; Lombart, Henry-Georges; Esikov, Kirill; Berniac, Joel; Liang, Kuang; Ji, Jingjing; Ptak, Roger G.; Madani, Navid; Cocklin, Simon; Bioorganic and Medicinal Chemistry Letters; vol. 24; 23; (2014); p. 5439 – 5445;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 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

2,3-Dichloro-5-nitropyridine (2 g, 10.36 mmol), 3-methyl-1H-1,2,4-triazole (1.722 g, 20.73 mmol) and Cs2CO3 (6.798 g, 20.73 mmol) were added to DMF (30 mL) and the reaction was stirred at rt for 12 h. The reaction mixture was quenched with water (200 mL). The mixture was extracted with ethyl acetate (100 mL*3). The organic layer was dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The crude residue was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate from 100:0 to 50:50) to afford a mixture of compounds 20a and 20a-1 (780 mg, 31%) as a white solid. A mixture of 3-chloro-2-(3-methyl-i H-i ,2,4-tri-azol- i -yl)-5-nitropyridine, 20a and 3-chloro-2-(5-methyl-i H-i ,2,4-triazol-i -yl)-5-nitropyridine, 20a- i (780 mg, i .63mmol) was dissolved in MeOH (20 mE), and Zn (0) (i.058g, i 6.28 mmol) and aqueous NH4C1 (20 mE) were added.The reaction mixture was stirred at rt for i 6 h. The reactionmixture was filtered though a pad of diatomaceous earth andthe pad washed with ethyl acetate (20 mEx3). Water (50 mE)was added and the organic layer was separated, dried overNa2SO4, filtered and the filtrate was concentrated to drynessto give a crude mixture of compounds 20b and 20b- i (400mg, 59%) as a yellow solid. ?H NMR (400 MHz, METHANOE-d 4) oe ppm 2.43 (s, 3H), 2.85 (d, J=0.66 Hz, iH), 2.99(s, iH), 7.2i-7.23 (m, iH), 7.82 (d, J=2.65 Hz, iH), 7.86(dd, J=4.85, 2.43 Hz, iH), 8.02 (s, iH), 8.6i-8.65 (m, iH),8.63 (s, iH).10965] A mixture of compounds 5-chloro-6-(3-methyl-1 H-i ,2,4-triazol- i -yl)pyridin-3-amine, 20b and 5-chioro-6- (5-methyl-i H-i ,2,4-triazol- i -yl)pyridin-3-amine, 20b- i (iOO mg, 0.3i mmol), i-(isoquinolin-4-yl)-5-(trifluorom- ethyl)-iH-pyrazole-4-carboxylic acid, 4c (263.0 mg, 0.63 mmol), and pyridine (62.0 mg, 0.78 mmol) were dissolved in dichioromethane (iO mE), and P0C13 (96.2 mg, 0.63 mmol) was added. The mixture was stirred at rt for 2.5 h. Sat. aqueous NH4C1 (20 mE) was added and the mixture was extracted with dichloromethane (20 mEx2). The combined organic layers were dried over Na2504, filtered, and the filtrates were concentrated under reduced pressure to afford a crude yellow oil. The crude oil was purified by reverse phase HPEC (A: water (0.05% HC1)-CAN, B: MeCN, AB:(48%/52%). The pure fractions were concentrated under reduced pressure and lyophilized to dryness to afford a mixture of compounds 53 and 54 (90 mg). The mixture was separated by Supercritical Fluid Chromatography (0.i% NH3H2O: MEOH. Mobile phase: A: CO2 B: 0.i% NH3H2O:MEOH; AB 75/25).10966] Cpd 53:10967] N-(5-chloro-6-(3-methyl- iH- i ,2,4-triazol-i -yl)pyridin-3-yl)- i -(isoquinolin-4-yl)-5-(trifluoromethyl)- iHpyrazole-4-carboxamide, (37.8 mg, 24.i%) as a white solid. ECMS (ESI) mlz M+i: 498.9. ?H NMR (400 MHz, DMSOd 5) oe ppm 2.34-2.40 (m, 3H), 7.27-7.30 (m, iH), 7.8i-7.90 (m, iH), 7.90-7.97 (m, iH), 8.33-8.4i (m, iH), 8.66-8.72 (m, iH), 8.74-8.82 (m, 2H), 8.86-8.98 (m, 2H), 9.60 (s, iH).10968] Cpd 54:10969] N-(5-chloro-6-(5-methyl-i H-i ,2,4-triazol-i -yl)pyridin-3-yl)- i -(isoquinolin-4-yl)-5-(trifluoromethyl)- iHpyrazole-4-carboxamide (i8.4 mg, 11.7%) as a white solid.ECMS (ESI) mlz M+i: 499.0. ?H NMR (400 MHz, DMSOd 5) oe ppm 2.34-2.37 (m, 3H), 7.23-7.32 (m, iH), 7.82-7.90(m, iH), 7.9i-7.98 (m, iH), 8.06-8.i2 (m, iH), 8.33-8.4i(m, iH), 8.59-8.64 (m, iH), 8.65-8.70 (m, iH), 8.75-8.8i(m, iH), 8.85-8.90 (m, iH), 9.58-9.64 (m, iH).

The synthetic route of 7170-01-6 has been constantly updated, and we look forward to future research findings.

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

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 7170-01-6 as follows. 7170-01-6

A mixture of 2-chloro-5-fluoropyrimidine (2.39 g, 18 mmol), 3-methyl-1H-1,2,4-triazole (1.5 g, 18 mmol), potassium carbonate (5 g, 36 mmol), potassium iodide (0.3 g, 1.8 mmol) and CH3CN (110 mL) were heated to 70 C for 18 h. The mixture was cooled to RT, diluted with CH2Cl2 (220 mL), filtered through Celite and the collected precipitate washed with CH2Cl2. The solid resulting from solvent evaporation was purified by chromatography (1-10% MeOH-CH2Cl2) and recrystallised from EtOAc to give the title compound (1.01 g, 5.64 mmol) as a colourless solid. 1H NMR (CDCl3, 300 MHz): delta 9.05 (s, 1H), 8.66 (s, 2H), 2.54 (s, 3H); LCMS (ESI) RT = 0.43 min, [M+H]+ 180.1.

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; BODIL VAN NIEL, Monique; CRIDLAND, Andrew; HURLEY, Christopher; KILLEN, Jonathan; WARD, Stuart; (203 pag.)WO2016/177686; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6,Some common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, molecular formula is C3H5N3, 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 mixture of 3 -methyl- IH-1, 2,4-triazole (8.12 g, 98 mmol), l,2,3-trifluoro-5-nitrobenzene (17.3 g, 98 mmol), and sodium bicarbonate (8.21 g, 98 mmol) in DMSO (100 mL) was heated at 800C for 24 h . The reaction mixture was allowed to cool to rt and was poured into water (800 mL). The aqueous mixture was extracted with EtOAc (3 x 200 mL). The combined organic extracts were sequentially washed with water (500 mL) and brine solution (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude reaction mixture was purified using silica gel chromatography (30-80% EtOAc/hexane, linear gradient) to afford a 1.7:1.0 mixture of two regioisomeric products as an orange solid. The orange solid was recrystallized from EtOAc (hot- cold) to provide 4.25 g of l-(2,6-difluoro-4-nitrophenyl)-3-melhyl-lH-l.,2,4-triazole as a white solid. The mother liquor was recrystalized from EtO Ac/Hex (hot-rt) to afford 1.89 g of l-(2,6-difluoro-4-nitrophenyl)-5-methyl-lH-l,2,4-triazole as a light yellow solid. The mother liquor was repeatly chromatographed under the previously stated conditions to provide two samples. One sample was partially enriched in the slightly less polar isomer, l-(2,6-difluoro-4~nitrophenyl)-3-memyl-lH-l,2,4-t?azole. The other sample was partially enriched in the slightly more polar isomer, l-(2,6- difluoro-4-nitrophenyl)-5-methyl-lH-l,2,4~triazoe. Both samples were independently recrystallized from EtO Ac/Hex to provide an additional 1.9 g of 1- (2,6-diiluoro-4-nitrophenyl)-3 -methyl- 1 H- 1 ,2,4-triazole and 1.37 g of l-(2,6- difluoro-4-nitrophenyl)-5-methyl- 1 H- 1 ,2,4-triazole. A combined total of 6.15 g (26 % yield) of 1 -(2,-difluoro-4-nitrophenyl)~3-methyl-l H- 1 ,2,4-triazole and 3.2 g (13% yield) of l-(2,6-difluoro-4-nitrophenyl)-5-methyl- IH-1 ,2,4-triazole was obtained.Data for 1 -(2 s6-difluoro-4-nitrophenyl)-3 -methyl- 1 H- 1 ,2,4-triazole: LC-MS(M+H)+ = 241.0. 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 8.34 (s, 1 H), 8.01- 8.10 (m, 2 H)5 2.54 (s, 3 H). Data for l-(2,6-difluoro-4-nitrophenyl)-5-methyl-lH-l,2,4-triazole: LC-MS(M+H)+ = 241.0. IH NMR (500 MHz, CHLOROFORM-d) delta ppm 8.08 (s, 1 H)5 8.04- 8.08 (m, 2 H), 2.45 (s, 3 H). An X-ray analysis of a single crystal grown from EtOAc/hexanes confirmed the regiochemical assignment of this isomer as the 5- methyl congener.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyl-1H-1,2,4-triazole, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life. 7170-01-6

A solution of 2,4-difluorobenzonitrile (7.07 g, 50.8 mmol) and 3-methyl-1H-1,2,4-triazole (4.22 g, 50.8 mmol) in N,N-dimethylformamide (45 ml) was treated with powdered anhydrous potassium carbonate (10 g) and the resulting mixture stirred at 22 C. for 18 h. The solid was then filtered and the filtrate concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, then dried over anhydrous magnesium sulfate and concentrated. The resulting mixture was purified by a combination of chromatography on silica gel (elution gradient of ethyl acetate in hexane) and reversed phase silica gel to yield intermediates 81-84. 4Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane); mp 117-118 C. 1HNMR 400 MHz (CDCl3) ? ppm: 2.54 (3H, s, CH3), 7.24 (1H, m, CH), 7.62 (1H, dd, J=2.5 Hz and J=9.1 Hz, CH), 7.84 (1H, dd, J=5.6 Hz and J=8.6 Hz, CH), 8.82 (1H, s, CH). Anal. Calcd for C10H7FN4: C, 59.40, H, 3.49, N, 27.71; Found: C, 59.25; H, 3.32; N, 27.81. 4-Fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane); mp 120-121 C. 1HNMR 400 MHz (CDCl3) ? ppm: 2.56 (3H, s, CH3), 7.30 (1H, dd, J=2.5 Hz and J=8.1 Hz, CH), 7.39 (1H, m, CH), 7.91 (1H, dd, J=5.5 Hz and J=8.6 Hz, CH), 8.06 (1H, s, CH). Anal. Calcd for C10H7FN4: C, 59.40, H, 3.49, N, 27.71; Found: C, 59.35; H, 3.70; N, 27.77. 2-Fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane); mp 133-134 C. 1HNMR 400 MHz (CDCl3) ? ppm: 2.52 (3H, s, CH3), 7.61 (1H, dd, J=2 Hz and J=9.1 Hz, CH), 7.67 (1H, dd, J=2 Hz and J=9.6 Hz, CH), 7.79 (1H, dd, J=6.5 Hz and J=8.6 Hz, CH), 8.56 (1H, s, CH). Anal. Calcd for C10H7FN4: C, 59.40; H, 3.49; N, 27.71; Found: C, 59.42; H, 3.24; N, 28.41. 2-Fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane); mp 89-90 C., 1HNMR 400 MHz (CDCl3) ? ppm: 2.69 (3H, s, CH3), 7.49-7.55 (2H, m, 2xCH), 7.83 (1H, dd, J=6.8 Hz and J=8.8 Hz, CH), 8.00 (1H, s, CH). Anal. Calcd for C10H7FN4: C, 59.40; H, 3.49; N, 27.71; Found: C, 59.17, H, 3.22, N, 28.01.

The chemical industry reduces the impact on the environment during synthesis 7170-01-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 7170-01-6 as follows. 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.

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sterling Drug Inc.; US4634772; (1987); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics