Category: 7170-01-6

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

Example 93Preparation of 4-(3-methyl-1H-1,2,4-triazol-1-yl)benzaldehyde (DI53); To a stiffing solution of 4-fluorobenzaldehyde (5.0 g, 40.32 mmol) in DMF (50 mL), were added K2CO3 (3.34 g, 40.32 mmol) and 3-methyl-1,2,4-trizole (3.34 g, 40.32 mmol) and the resultant reaction mixture was stirred at RT for 4 h. After completion of the reaction (TLC), the reaction mixture was diluted with water and extracted with EtOAc (3×). The combined EtOAc layer was washed with water and brine then dried over Na2SO4 and concentrated under reduced pressure to afforded the title compound as a white solid (4.1 g, 60%): mp 125-128 C.; 1H NMR (400 MHz, CDCl3) delta 10.05 (s, 1H), 8.76 (s, 1H), 8.02 (d, 2H), 7.85 (d, 2H), 2.50 (s, 3H); ESIMS m/z 188.04 ([M+H]+).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Hunter, James E.; Lo, William C.; Watson, Gerald B.; Patny, Akshay; Gustafson, Gary D.; Pernich, Dan; Brewster, William K.; Camper, Debra L.; Lorsbach, Beth; Loso, Michael R.; Sparks, Thomas C.; Joshi, Hemant; Mandaleswaran, Adiraj; Sanam, Ramadevi; Gundla, Rambabu; Iyer, Pravin S.; US2012/329649; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 7170-01-6, 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.

To a magnetically stirred solution of 2-(difluorom- ethyl)-i-fluoro-4-nitrobenzene (2 g, 10.47 mmol) in DMSO (10 mE) at 0 C. were added K2C03 (1.446 g, 10.47 mmol) and 3-methyl-1H-i,2,4-triazole (0.870 g, 10.47 mmol). The reaction mixture was allowed to warm to RT and stirred overnight, poured into ice and extracted with EtOAc (50 mE, twice). The combined organic layers were washed with brine, dried over Na2504, and concentrated under reduced pressure. The residue was purified on l3iotage using a 0-20% gradient of EtOAc in petroleum ethet Two sets of fractions with desired product mass were isolated, one of which was confirmed to be the desired nitro triazole product by x-ray crystal analysis. ?H NMR (400 MHz, CHEOROFORM-d) oe 400 MHz: 8.74-8.73 (1H, d, J=2.i Hz), 8.51-8.47 (1H, m),8.39 (1H, s), 7.70-7.67 (1H, d, J=8.4), 7.39-7.02 (1H, t, J=54), 2.53 (3H, s). ECMS M+H=255.2.

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; BRISTOL-MYERS SQUIBB COMPANY; MCDONALD, Ivar M.; SIVAPRAKASAM, Prasanna; IWUAGWU, Christiana I.; Peese, Kevin M.; CHENG, Heng; CHOWDARI, Naidu S.; GANGWAR, Sanjeev; (75 pag.)US2018/110873; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 7170-01-6, 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.

General procedure: To a mixture of 33 (126.3 mg,0.295 mmol) and 1H-pyrazole (24.1 mg, 0.353 mmol) in DMF(4 mL) was added K2CO3 (48.8 mg, 0.353 mmol). The mixturewas stirred at 90C for 30 min and then poured into water.The mixture was extracted with EtOAc, washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified bycolumn chromatography (silica gel, hexane-ethyl acetate,19 : 1 to 0 : 100) to afford 14 (102 mg, 0.222 mmol, 75%) as awhite solid after trituration with hexane-ethyl acetate (5 : 1).1H-NMR (300 MHz, DMSO-d6) delta: 1.02 (3H, s), 1.36 (3H,s), 4.86 (1H, d, J=8.3 Hz), 5.34 (1H, s), 6.75-6.81 (1H, m),7.23-7.33 (2H, m), 7.48-7.58 (2H, m), 7.76 (1H, d, J=7.5 Hz),8.05 (1H, d, J=1.5 Hz), 8.46 (1H, s), 9.02-9.14 (2H, m), 9.37(1H, d, J=7.5 Hz). MS (ESI/APCI) m/z 461.1 [M+H]+. HPLCpurity: 100%. mp 241C.

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:
Article; Mikami, Satoshi; Kawasaki, Masanori; Ikeda, Shuhei; Negoro, Nobuyuki; Nakamura, Shinji; Nomura, Izumi; Ashizawa, Tomoko; Kokubo, Hironori; Hoffman, Isaac Dylan; Zou, Hua; Oki, Hideyuki; Uchiyama, Noriko; Hiura, Yuuto; Miyamoto, Maki; Itou, Yuuki; Nakashima, Masato; Iwashita, Hiroki; Taniguchi, Takahiko; Chemical and Pharmaceutical Bulletin; vol. 65; 11; (2017); p. 1058 – 1077;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 7170-01-6, These common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-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.

To a solution of 3-methyl-1 H-1 ,2,4-triazole (1 g) in MeCN (40mL) was added Cs2C03 (3.72g) followed by benzyl bromoacetate (1 .89mL) and the mixture was stirred for 1 h at RT. The reaction mixture was diluted with EA and washed with water (2x) and brine. The aq. layers were extracted with EA (2x) and the combined org. layers were dried over MgS04, filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 100g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8:2; gradient in %B: 85/15 for 12CV, 85/15 to 75/25 for 2CV, 75/25 for 3CV) to afford 2.3g as yellowish oil (52:48 mixture of regioisomers). The mixture of regioisomers was purified by preparative chiral HPLC (I). Second eluting fraction: (3-methyl-[1 ,2,4]triazol-1-yl)-acetic acid benzyl ester. LC-MS (A): tR = 0.67min; [M+H]+: 232.16. 1 H-NMR (CDCI3): 8.05 (s, 1 H); 7.40-7.30 (m, 5H); 5.23 (s, 0.95H, CH2); 4.93-4.88 (3s, 2H); 2.42 (s, 3H). Roesy signal seen between CH (triazole) at 8.05ppm and CH2 at 4.93-4.88ppm.

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

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; CAROFF, Eva; MEYER, Emmanuel; (32 pag.)WO2018/11265; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7170-01-6, These common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-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.

General procedure: To 3,6-dichloropyridazine (500 mg, 3.36 mmol) in 5 mL DMF are added 1H-1,2,4-triazole (460 mg, 6.71 mmol) and cesium carbonate (2.41 g, 7.38 mmol) and the reaction mixture is stirred at 60 C. for 18 h. The mixture is quenched with water and the precipitation is filtered, washed and dried to give 0.7 g of the product. (0171) C8H6N8 (M=214.19 g/mol) (0172) ESI-MS: 215 [M+H]+ (0173) 1H NMR (400 MHz, DMSO-d6) delta=9.66 (s, 1H), 8.47 (s, 1H), 8.44 (s, 1H)

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

Reference:
Patent; Boehringer Ingelheim International GmbH; Larsen, Janus Schreiber; Binder, Florian; Cui, Yunhai; Hucke, Oliver; Lipinski, Radoslaw; Montel, Florian; Ostermeier, Markus; Perera, Alexandre; Peters, Stefan; US2020/24261; (2020); 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. HPLC of Formula: C3H5N3

Step 212.1: To a solution of 3-methyl-1H-1,2,4-triazole (1 g) in MeCN (40 mL) was added Cs2CO3 (3.72 g) followed by benzyl bromoacetate (1.89 mL). The reaction mixture was stirred at RT for 1 h and evaporated to dryness. The residue was taken up in EA and washed with water, sat. NH4Cl and brine. The aq. layers were extracted with EA, the combined org. layers were dried (MgSO4), filtered off and evaporated in vacuo. The residue was purified by CC (Biotage, SNAP 100 g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in % B: 15 for 12CV, 15 to 25 over 2CV, 25 for 3CV) to afford 2.23 g of oil. The oil was purified by preparative chiral HPLC (II) to afford the two regioisomers, both as mixture of benzyl and ethyl ester that formed during the evaporation of the fractions after HPLC purification. The second eluting compound also contains the methyl ester analog due to the addition of MeOH to the fractions before evaporation. [0921] First eluting compound: (5-Methyl-[1,2,4]triazol-1-yl)-acetic acid benzyl ester (1.07 g, brown oil, contains 16% of the ethyl ester analog). LC-MS (B): tR=0.68 min; [M+H]+: 232.16. 1H-NMR (CDCl3): 7.83 (s, 1H); 7.40-7.33 (m, 5H); 5.23 (s, 2H); 4.93 (s, 2H); 2.43 (s, 3H). Roesy signal seen between CH2 at 4.93 ppm and CH3 at 2.43 ppm. [0922] Second eluting compound: (3-Methyl-[1,2,4]triazol-1-yl)-acetic acid benzyl ester (1.15 g, yellow oil, contains 30% of the ethyl ester and 20% of the methyl ester analogs). LC-MS (B): tR=0.67 min; [M+H]+: 232.16. 1H-NMR (CDCl3): 8.05 (s, 1H); 7.40-7.30 (m, 5H); 5.23 (s, 0.95H, CH2 of benzyl ester); 4.93-4.88 (3s, 2H); 4.27 (q, 0.58H, CH2 of ethyl ester); 3.81 (s, 0.65H, CH3 of methyl ester); 2.42 (s, 3H). Roesy signal seen between CH at 8.05 ppm and CH2 at 4.93-4.88 ppm.

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; Caroff, Eva; Keller, Marcel; Kimmerlin, Thierry; Meyer, Emmanuel; US2014/371204; (2014); 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. Quality Control of 3-Methyl-1H-1,2,4-triazole

E) tert-butyl 6-methyl-5-(3-methyl-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate To a solution of tert-butyl 5-chloro-6-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate (1.08 g) in N,N-dimethylformamide (20.2 mL) were added 3-methyl-1H-1,2,4-triazole (469 mg) and potassium carbonate (781 mg) at room temperature. The reaction mixture was stirred at room temperature under an atmosphere dried with calcium chloride, and stirred overnight and then at 60 C. for 2 hr. The reaction mixture was cooled to room temperature, and water was added. The resulting solid was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (870 mg) containing a regioisomer. MS (API+): [M+H]+315.2.

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kawasaki, Masanori; Mikami, Satoshi; Nakamura, Shinji; Negoro, Nobuyuki; Ikeda, Shuhei; Nomura, Izumi; Ashizawa, Tomoko; Imaeda, Toshihiro; Seto, Masaki; Sasaki, Shigekazu; Marui, Shogo; Taniguchi, Takahiko; (130 pag.)US2016/159808; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 7170-01-6, 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.

To a stirred solution of compound GX (i g, 2.91 mmol) in DMF (10 mL) under argon atmosphere were added potassium carbonate (602 nig, 4.36 mmol) and 3-methyl-lH-l ,2,4- triazoie (483 mg, 5.82 mmo) at RT. The reactioii mixture was stirred at 80 C for 16 Ii. The reaction mixture was diluted with water (50 mL) and extracted with EfOAc (2 x 50 mL). The combined organic layers were dried over anhydrous NaiSC^ and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluent: 50% EtOAc/Hexane) which was further purified by preparative HPLC to afford compound JL (550 nig, 1.29 mmol, 44%) & compound JM (550 nig. 1.2 mniol, 44%) as an off-white solids. JL data: 5H NMR (500 MHz, DMSO-(): 5 8.71 (s, 1H), 8.15 (dd, J= 8.7, 2.3 Hz, 1H), 8.01 (s, 1H), 7.37 (d, J = 8.1 Hz, 1H), 7.31-7.24 (ni. IH), 7.24-7.18 (in, 1H), 7.17-7.14 (m, 1H), 7.09- 7.05 (m, 1H), 6.79 (s, IH), 5.15 (d, J = 14.5 Hz, 1H), 4.75 (d, J= 15.1 Hz, IH), 2.04 (s, 3H); JM data: 1H NMR (500 MHz, DMSO-?): S 8.71 (s, 1H), 8.17 (dd, J= 8.1, 2.3 Hz, 1H)5 7.56 (s, 1H), 7.44 (d J= 8.1 Hz, lH), 7.33-7.27 (ni, 1H), 7.26-7.22 (m, IH), 7.19-7.16 (m, 1H), 7.10-7.06 (m, 1H), 6.66 (s, 1H). 4.98 (d, /= 14.49 Hz, IH), 4.86 (d. /= 13.91 Hz, IH), 2.22 (s, 3H).

The synthetic route of 3-Methyl-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; YATES, Christopher, M.; SHAVER, Sammy, R.; HOEKSTRA, William, J.; (455 pag.)WO2017/117393; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 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) 1-(2-Fluoro-4-nitro-phenyl)-5-methyl-1H-[1,2,4]triazole; 3,4-Difluoronitrobenzene (514 mg, 3.23 mmol), 3-methyl-1H-1,2,4-triazole (325 mg, 3.72 mmol) and di-potassium hydrogen phosphate trihydrate (1.49 g, 6.46 mmol) in dimethyl sulfoxide (1.5 mL) were stirred for 6 hours at 70 C. The mixture was concentrated in vacuo; the residue was diluted in water and extracted three times with ethyl acetate. The combined organic layers were washed four times with water, twice with brine, dried with magnesium sulfate and evaporated. Column chromatography (30 g silica, heptane/ethyl acetate 1:1 v/v) afforded the title compound (160 mg, 22%) as white crystals MS ISP (m/e): 223.2[(M+H)+]. 1H NMR (CDCl3, 300 MHz): delta (ppm)=8.22 (m, 2H), 8.04 (s, 1H), 7.74 (dd, 1H), 2.48 (d, 3H). Mp 56-58 C.

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; Baumann, Karlheinz; Flohr, Alexander; Goetschi, Erwin; Jacobsen, Helmut; Jolidon, Synese; Luebbers, Thomas; US2009/215759; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 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.

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 45-48. 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) delta 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. 1HNMR400 MHz (CDCl3) delta 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) delta 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) delta ppm: 2.69 (3H, s, CH3), 7.49-7.55 (2H, m, 2 x CH), 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.

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