Triazoles

Electric Literature of 288-88-0, 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. 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.

Step 1. Preparation of (1H-1,2,4-triazol-1-yl)methanol A mixture of 1H-1,2,4-triazole (7.04 g, 102 mmol), paraformaldehyde (3.06 g, 102 mmol) and catalytic amount of triethylamine was heated to molten condition and stirred at the same temperature (140 C.) for 0.5 hour. Reaction mixture was then cooled to 30 C. to obtain the product (9.0 g, 89%) as white solid.

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

Reference:
Patent; CADILA HEALTHCARE LIMITED; DESAI, Ranjit C.; PINGALI, Harikishore; (40 pag.)US2016/83380; (2016); A1;,
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. Formula: C2H3N3

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1 ,2,3-triazole (2.1 g, 30.5 mmol), CsCO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dirnethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to rt, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 50% EtOAc in water with 0.1% TFA) to give the desired A-3. A portion of this acid (0.1 1 g, 0.53 mmol) was treated with thionyl chloride (0.59 g, 5.3 mmol) in dichloromethane (5.0 mL) at rt. After stirring at RT for 1 h, the mixture was concentrated, azeotroping with benzene to yield acid chloride A-3.

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/11775; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 4314-22-1,Some common heterocyclic compound, 4314-22-1, name is 2-(1H-1,2,3-Triazol-1-yl)acetic acid, molecular formula is C4H5N3O2, 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 PyBOP (0.08 mmol in 200 mL of DMF), {[3′-(1- piperazinylmethyl)-3-biphenylyl] methyl} amine (44 mmol in 200 mL of DMF) and DIPEA (30 mL) were added to 1 H-1, 2, 3-triazol-1-yl acetic acid (0.07 mmol). The resulting mixture was stirred for 16 hours at room temperature, the solvent was then removed under vacuum. The residue was re-dissolved in methanol and purified by loading onto a SPE cartridge (SCX, 500 mg), washing with MeOH (5 mL), and eluting with a 2M solution of NH3 in MeOH (5 mL). The NH3 fraction was collected and evaporated under vacuum to give a gum which was re-dissolved in 1: 1 CHO3/ TFA (0.5 mL). After stirring for 2 hours, the solvent was removed under vacuum and the residue was purified by MDAP to give the desired compound as a TFA salt. The free base of the compound was obtained by loading the salt onto a SPE cartridge (SCX, 500 mg), washing with MeOH, and eluting with 2M NH3/MeOH. The ammonia fraction was collected and the solvent was removed under vacuum to give the title compound (11.1 mg, 65%). LC/MS: m/z, 391 (M+H), 2. 04 min.

The synthetic route of 4314-22-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/87236; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 13273-53-5, These common heterocyclic compound, 13273-53-5, name is 4-Bromo-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) [4-(l-methyl-lH-l,2,3-triazol-4-yl)phenyl]methanol A mixture of [ 4- (hydroxymethyl ) henyl] boronic acid (7.10 g) , 4-bromo-l-methyl-lH-l, 2-3-triazole (5.00 g) , sodium carbonate (6.59 g) and tetrakis (triphenylphosphine)palladium(O) (3.59 g) in a mixed solvent of water (30.0 mL) -1, 4-dioxane (100 mL) was heated with reflux for 16 hr under nitrogen atmosphere. The reaction mixture was allowed to be cooled to room temperature, the organic layer was concentrated under reduced pressure, and the residue was extracted with dichloromethane (x 3) . The combined extracts were dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (3.40 g) . MS: [M+H]+ 189.9.

The synthetic route of 13273-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMADA, Masami; SUZUKI, Shinkichi; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; KAMATA, Makoto; WO2015/163485; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-65-5,Some common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-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 solution of 1-methyl-1H-1,2,3-triazole (12.9 g, 155 mmol) in THF (260 mL) was cooled to -45 C. Maintaining a temperature of <-35 C., n-BuLi (62.1 mL, 2.5 M in hexanes, 155 mmol) was added over 10 minutes. The reaction mixture was stirred for 30 minutes with cooling to -45 C. and then treated with a sub-surface stream of CO2(g) for a period of 2 hours. After flushing the -35 C. slurry with N2(g) for 5 minutes, thionyl chloride (11.8 mL, 163 mmol) was added. The mixture was allowed to warm to room temperature with stirring over 1.25 hours. Then, N,O-dimethylhydroxylamine hydrochloride (18.14 g, 186 mmol) and N,N-diisopropylethylamine (68.3 mL, 396 mmol) were added and the resulting mixture stirred for 15 hours. Aqueous sodium carbonate (500 mL, 10 wt %) was then added, and the layers were mixed and separated. The aqueous layer was washed with dichloromethane (250 mL and then 125 mL), and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was taken up in ethyl acetate (225 mL), treated with MgSO4, and filtered through a pad of silica gel (115 g). The silica gel pad was washed with additional ethyl acetate (800 mL). The eluent was concentrated to provide the title compound as a yellow solid. The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H7N3O2

(R) or (S) – benzyl 5-methyl-4-r2-(2H-1.2,3-tria2thetal-2-yl’)benzoyl1-l,4-diazepane-l-carboxylate (B-4)To a solution of 250 mg (1.0 mmol) of the first eluting enantiomer B-2, 200 mg (1.05 mmol) B-3, 185 mg (1.2 mmol) 1-hydroxybenzotriazole hydrate, and 421 muL (3.0 mmol) triethylamine in 3 mL of DMF was added 289 mg (1.5 mmol) EDC and the reaction was stirred 4 h at 5O0C. The reaction was partitioned between EtOAc and saturated aqueous NaetaCtheta3. The layers were separated and the organic was washed with water, brine, dried over MgSO4 and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel (EtOAc/hexanes) to provide B-4 as a colorless gum. Data for B-4: LC/MS: rt = 2.25 min; m/z (M -I- H) = 420.0 found; 420.2 required.

According to the analysis of related databases, 1001401-62-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2008/8518; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1455-77-2, A common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, 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 mixture of Zn(NO3)2¡¤6H2O (0.030 g, 0.1 mmol), H3btc (0.024 g, 0.1 mmol), Hdatrz (0.01 g, 0.10 mmol), NaHCO3 (0.025 g, 0.3 mmol) and H2O (10 mL) was placed in a 23 ml Teflon-lined stainless steel reactor under autogenous pressure at 160 ¡ãC for 60 h and then cooled to the room temperature slowly. Colorless prism crystals were obtained in 34percent yield based on Zn(NO3)26H2O. Anal. calcd. for C11H7N5O6Zn2 (436.00): C, 30.28; H, 1.61; N, 16.06percent. Found: C, 30.31; H, 1.58; N, 16.02percent. IR (KBr, cm?1) 3387(s), 3175(m), 1607(s), 1566(s), 1395(s), 1366(m), 1307(w), 1224(m), 1077(s), 853(w), 718(s), 688(m), 647(w).

The synthetic route of 1455-77-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cui, Penglei; Li, Xiaohui; Journal of Molecular Structure; vol. 1081; (2015); p. 182 – 186;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 930-33-6, name is 1H-1,2,4-Triazol-3(2H)-one, molecular formula is C2H3N3O, 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. COA of Formula: C2H3N3O

To a solution of 29 (2.0g, 23.5mmol, 1.0 equiv.) in DCM (20mL), (BOC)2O (5.1g, 23.5mmol, 1.0 equiv.), DMAP (0.287g, 2.35mmol, 0.1 equiv.) and DIPEA (10.0mL, 58.7mmol, 2.5 equiv.) were added. The reaction was stirred at room temperature for 18h. The reaction mixture was concentrated under reduced pressure and purified by flash chromatography using DCM/MeOH (20:1, v/v) as mobile phase. Yield, 14%. 1H NMR (400MHz, DMSO-d6) delta 1.50 (s, 9H), 7.98 (s, 1H) ppm. 13C NMR (100MHz, DMSO-d6) delta 27.97, 85.83, 136.53, 147.15, 153.68ppm. ESI-MS for C7H11N3O [M-H]- 184.12.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 930-33-6, its application will become more common.

Reference:
Article; Fonovi?, Ur?a Pe?ar; Knez, Damijan; Hrast, Martina; Zidar, Nace; Proj, Matic; Gobec, Stanislav; Kos, Janko; European Journal of Medicinal Chemistry; vol. 193; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 4922-98-9, 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 4922-98-9 as follows.

Into a 50-mL round-bottom flask, was placed 3-phenyl-lH-l,2,4-triazol-5-amine (246 mg, 1.54 mmol, 1.00 equiv) in DMF (15 mL), HOBT (311 mg, 2.30 mmol, 1.50 equiv), EDCI (440 mg, 2.30 mmol, 1.50 equiv) and triethylamine (466 mg, 4.61 mmol, 3.00 equiv). Then 6-fluoro-l,2,3,4-tetrahydroquinoline-4-carboxylic acid (300 mg, 1.54 mmol, 1.00 equiv) was added in 2 mins later. The resulting mixture was stirred for 3 h at room temperature (25 ¡ãC). The reaction was then poured into 50 mL of water. The resulting solution was extracted with ethyl acetate (70 mL x 3), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied on a silica gel column and eluted with ethyl acetate/hexane (3/10). The collected fraction was concentrated to give 136.6 mg (26percent) of (5-amino-3- phenyl-lH-l,2,4-triazol-l-yl)(6-fluoro-l,2,3,4-tetrahydroquinolin-4-yl)methanone (17) as an off-white solid. MS (ES, m/z) [M+H]+: 338; HNMR (DMSO-^6, 300MHz ,ppm): delta 8.05- 8.00 (m, 2H), 7.70 (s, 2H), 7.53-7.48(m,3H), 6.89-6.79 (m, 2H), 6.55-6.52 (m, 1H), 5.87 (s, 1H), 4.95 (m, 1H), 3.26-3.18 (m, 2H), 2.23-2.145 (m, 1H), 2.13-2.08 (m, 1H).

According to the analysis of related databases, 4922-98-9, the application of this compound in the production field has become more and more popular.

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

Synthetic Route of 3179-31-5,Some common heterocyclic compound, 3179-31-5, name is 1H-1,2,4-Triazole-3-thiol, molecular formula is C2H3N3S, 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.

Step B–Cyclobutylmethyl 1,2,4-Triazol-3-yl Sulfide To a solution of 1,2,4-triazole-3-thiol (20.2 g; 0.20 mol) and sodium methoxide (11.8 g; 0.22 mol) in methanol (250 ml) is added cyclobutylmethyl methanesulfonate (36.4 g; 0.22 mol). The mixture was refluxed for 27 h under dry nitrogen, allowed to cool to 25 C. and filtered. The solid was washed with ethyl acetate and the organic solutions combined and evaporated. The residue was dissolved in water (250 ml) and extracted into ethyl acetate (250 ml) and dichloromethane (100 ml). The extracts were combined, dried (Na2 SO4), filtered and evaporated to afford crude cyclobutylmethyl 1,2,4-triazol-3-yl sulfide (21.8 g; 65%) as a white, sticky solid. NMR -d(CDCl3; 60 MHz) 1.5-2.8 (m), 3.2 (2H, d, J=7 Hz), 8.0 (1H, s) and 12.4 (1H, br s).

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

Reference:
Patent; Rohm and Haas Company; US5308830; (1994); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics