Month: April 2021

Application of 1455-77-2,Some common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, 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 10 mmol of 1,2,4-triazole-3,5-diamine, pyridine-2,6-diamine, or 4-hydroxypyrimidine-2,6-diamine in 50 mL of glacial acetic acid was slowly added to a solution of 20 mmol of phthalic anhydride or tetrachlorophthalic anhydride in 100 mL of glacial acetic acid. The colored solution was refluxed with constant stirring for 8 h at 100 ¡ãC (TLC monitoring; MeOH?CH2Cl2, 1 : 4) and poured into cold water. The colored precipitate was filtered off, dried in a vacuum desiccator over fused CaCl2, and recrystallized from DMSO. 2,2?-(1H-1,2,4-Triazole-3,5-diyl)bis[1H-isoindole-1,3(2H)-dione] (1). Yield 66percent, white solid, mp >300¡ãC. IR spectrum, nu, cm?1: 1793, 1743 (C=O), 3298 (N?H),691 [delta(C?Carom)]. 1H NMR spectrum, delta, ppm: 7.60 d (4H, Harom), 7.69 d (4H, Harom), 11.13 s (1H, NH). Mass spectrum: m/z 360.01 [M + 1]+. Found, percent: C60.12; H 2.47; N 19.54. C18H9N5O4. Calculated, percent: C60.17; H 2.52; N 19.49.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Diamino-1,2,4-triazole, its application will become more common.

Reference:
Article; Arif; Nayab, P. Sirajuddin; Rahisuddin; Russian Journal of General Chemistry; vol. 86; 6; (2016); p. 1374 – 1380; Zh. Obshch. Khim.; vol. 86; 6; (2016); p. 1374 – 1380,7;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 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 solution of n-BuLi (2.5 M in hexanes, 1.25 mL, 3.12 mmol) was added dropwise by syringe to a solution of 1-methyl-1H-1,2,3-triazole (268 mg, 3.22 mmol) in dry THF (32 mL) in a dry ice-methanol bath. The suspension was stirred for 30 minutes, slowly allowing the reaction mixture to warm to -10 C. (4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (0.500 g, 1.05 mmol, Intermediate 45: step f) in dry THF (5 mL) was added to the mixture via syringe and the resulting mixture was allowed to warm to ambient temperature overnight. The reaction was quenched with water. Brine was added and the aqueous mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-8% MeOH-DCM) to provide the title compound. 1H NMR (500 MHz, CDCl3) delta 8.69 (d, J=1.7 Hz, 1H), 8.24 (d, J=1.9 Hz, 1H), 8.22 (s, 1H), 7.79-7.76 (m, 1H), 7.75 (d, J=8.7 Hz, 1H), 7.57 (d, J=8.1 Hz, 1H), 7.42 (dd, J=8.7, 2.0 Hz, 1H), 6.97 (s, 1H), 5.95 (s, 1H), 4.30 (s, 2H), 4.08 (s, 3H), 3.88 (s, 3H), 3.33 (s, 3H), 2.12 (s, 3H); MS m/e 557.8 [M+H]+.

Statistics shows that 1-Methyl-1H-1,2,3-triazole is playing an increasingly important role. we look forward to future research findings about 16681-65-5.

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

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, A new synthetic method of this compound is introduced below., category: Triazoles

In a 500 mL round-bottomed flask, lH-l,2,4-triazole-3,5-diamine (1.5 g, 15.1 mmol, Eq: 1.00) and sodium methoxide 1M (33.3 ml, 16.7 mmol, Eq: 1.1) were combined with MeOH (100 ml) to give a colorless turbid solution. The reaction mixture was stirred for 4 hr and stripped to a gray solid. Suspended in 30 ml DMF and l-(chloromethyl)-4-methoxybenzene (2.42 g, 2.1 ml, 15.4 mmol, Eq: 1.02) was added. The dark brown suspension was stirred at 25C for 60 hrs under argon. The reaction was diluted with water (35 ml) and extracted with EtOAc (3 x 50 ml). The organic layers were combined, washed with H20 (1 x 25 mL), sat NaCl (1 x 50 ml), dried over Na2S04 and concentrated in vacuo to a white pasty solid. Dried under vacuum while gently heating to remove residual DMF and PMB-C1. The crude material was purified by flash chromatography (silica gel, 80g, 0percent to 10percent MeOH in DCM) to give 457 mg of desired product as a yellow solid (14percent). MS (m+1) = 220.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHEN, Zhi; CHIN, Elbert; ERICKSON, Shawn David; GABRIEL, Stephen Deems; MERTZ, Eric; WEIKERT, Robert James; WO2014/135483; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 4928-87-4, 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 4928-87-4 as follows.

Example 2. Synthesis of N-{4-[(pyrimidin-2-yl)sulfamoyl]phenyl}-lH-l,2,4- triazole-3-carboxamide, 1-18 1-18 [00267] Compound 1-18 was prepared according to the reaction sequence in Scheme IV with several adaptations. The solvent was removed in vacuo, the remaining material was triturated from H2O/CH3CN 1 : 1 (20ml), washed with small volumes of DMSO/CH3CN 1 :2, collected and dried to afford 190mg (65%) of N-{4-[(pyrimidin-2-yl)sulfamoyl]phenyl}-lH-l,2,4-triazole-3- carboxamide 1-18 as a colourless solid. 1H NMR (500 MHz, DMSO-d6) delta 14.84 (s, 1H), 11.70 (s, 1H), 10.83 (s, 1H), 8.66 (s, 1H), 8.50 (d, J = 4.9 Hz, 2H), 8.02 (d, J = 8.9 Hz, 2H), 7.95 (d, J = 8.9 Hz, 2H), 7.04 (t, J = 4.9 Hz, 1H).

According to the analysis of related databases, 4928-87-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RAZE THERAPEUTICS, INC.; SAIAH, Eddine; (148 pag.)WO2016/40449; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 6818-99-1, 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 6818-99-1 as follows.

Under an atmosphere of argon, (2S,4R)-N-(1-cyanocyclopropyl)-4-(4-fluoro-2- methyiphenylsulfonyl)- 1 -(1 -(trifluoromethyl)cyclopropanecarbonyl)pyrrolidine-2- carboxamide (example 19, step b, 0.2 g, 410 imol) was combined with N,Ndimethylacetamide (8.00 mL) to give a colorless suspension. 3-Chloro-1H-1,2,4-triazole (86.7 mg, 821 imol) and cesium carbonate (267 mg, 821 imol) were added. The reactionmixture was stirred over 5 days and was subsequently heated to 140C for 30 mm in a microwave oven. The reaction mixture was then poured into water (40 mL) and extracted with ethyl acetate (2 x 40 mL). The crude material was purified by preparative HPLC and obtained as a light yellow, viscuous oil (12 mg, 5.1%). mlz = 571.11 [M+H41.:_The title compound was obtained as a by-product in the preparation of example 66 and was obtained as a light yellow viscous oil (13.9 mg, 5.9%, stereochemistry assigned byNOESY-NMR). mlz = 571.1137 [M+H?i.

According to the analysis of related databases, 6818-99-1, the application of this compound in the production field has become more and more popular.

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

Adding a certain compound to certain chemical reactions, such as: 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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 6523-49-5, Recommanded Product: 4-(1,2,4-Triazol-1-yl)aniline

Example 7 Part A To a solution of 1 (80 mg, 0.5 mmol) in DMF (5 mL) at 0 C., HOBt (135 mg, 1.0 mmol) was added, followed by EDCI (191 mg, 1.0 mmol). After stirring at 0 C. for 0.5 h, 4-[1,2,4]triazol-1-yl-phenylamine (80 mg, 0.5 mmol) was added. 4-Methoxy-2-methyl-phenylamine (70 mg, 0.5 mmol) was added 10 min later. The reaction was then warmed up to RT and was stirred at this temperature for overnight. Water was added and the formed precipitated was collected by filtration, which was purified using prep-HPLC to give the desired product (30 mg). LC-MS m/z 418.2 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1,2,4-Triazol-1-yl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation; US2007/43045; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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. Product Details of 956317-36-5

To a solution of the acid (10.4 g, 51.2 mmol) in THF (250 mL), CDI (8.7 g, 53.7 mmol) was added. After 3.5 h, aqueous NH3 solution (174.1 g, 25% in water, 2.56 mol) was added. The biphasic mixture was stirred at room temperature for 75 mm. The pH was adjusted to pH 7 with 6 N HC1 and DCM were added. The layers were separated and the organic layer was washed with water, dried over Na2504 and the solvent was removed under reduced pressure. The residue was stirred with diethyl ether for 30 mm, filtered and washed with diethyl ether to give 7.9 g (76 %) of the primary amide.1H NMR (300 MHz, d6-dmso) oe = 8.01 (s, 2H, Htriazoiyi), 7.79 (br s, 1H, NH), 7.61 (d, J =8.1 Hz, 1H, Harom), 7.40 (d, J = 8.4 Hz, 1H, Harom), 7.38 (s, 1H, Harom), 7.32 (br s, 1H, NH),2.40 (s, 3H, CH3).13C NMR (75 MHz, d6-dmso) oe = 168.6, 138.0, 135.8, 134.6, 132.0, 130.5, 129.0, 123.8,20.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 956317-36-5, its application will become more common.

Reference:
Patent; SANDOZ AG; HOeFERL-PRANTZ, Kathrin; BARTH, Roland; RICHTER, Frank; ZUPANCIC, Borut; (126 pag.)WO2016/20403; (2016); 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. 49607-51-4, name is 1-Methyl-1H-1,2,4-triazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Methyl-1H-1,2,4-triazol-3-amine

Triphosgene (0.588 g, 1.982 mmol) was added to a stirred solution of (4S)-7-(2- methylpyridin-4-yl)-2,3,4,5-tetrahydro-l,4-methanopyrido[2,3-b][l,4]diazepine (0.5g, 1.982 mmol) in tetrahydrofuran (20 mL) at 0 C and stirred for 30min. Triethylamine (0.829 mL, 5.94 mmol) and 1 -methyl- lH-l,2,4-triazol-3 -amine (0.486 g, 4.95 mmol) was added at 0 C. The reaction mixture was stirred for 48h at 70 C. The reaction mixture was cooled to 28 C, and was partitioned between water (50 mL) and DCM (50 mL). The separated organic layer was washed with water and brine. The organic layer was dried over anhydrous Na2SC”4, filtered and filtrate was evaporated to afford crude yellow solid (TLC eluent: 10% MeOH in EtOAc: Rr0.3; UV active). The crude compound was purified by (100-200 mesh) silica gel and was eluting with 5% MeOH in ethyl acetate to afford (4S)-N-(1 -methyl- H- 1 ,2,4-triazol-3 -yl)-7-(2-methylpyridin-4-yl)-3,4-dihydro- 1 ,4- methanopyrido[2,3-6][l,4]diazepine-5(2H)-car-boxamide (0.215g, 0.563 mmol, 28.4 % yield) as light yellow solid, LCMS (m/z): 377.28 [M+H]+.1H NMR (400 MHz, DMSO-i): delta 13.44 (s, 1H), 8.55 (d, J = 5.2 Hz, 1H), 8.36 (s, 1H), 7.96 (s, 1H), 7.86 – 7.61 (m, 3H), 5.44 (dd, J = 5.8, 3.0 Hz, 1H), 3.83 (s, 3H), 3.27 (d, J = 30.5 Hz, 3H), 2.95 (dd, J= 12.0, 3.2 Hz, 1H), 2.59 (s, 3H), 2.23 (ddt, J= 16.9, 9.7, 4.4 Hz, 1H), 1.91 (dt, J= 14.7, 7.4 Hz, 1H).

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 49607-51-4.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-67-7,Some common heterocyclic compound, 16681-67-7, name is 4-Bromo-2-methyl-2H-1,2,3-triazole, molecular formula is C3H4BrN3, 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.

4H-[ l,2,4]Triazolo[4,3-a ][ l,5]benzodiazepine, 5, 6-dihydro-l,4-dimethyl-8-( 2- methyl-2H-l,2,3- triazole-4-yl)-6-(4-cyano-phenyl) ( Compound 109). A solution of 4H- [l,2,4]Triazolo[4,3-a][l,5] benzodiazepine, 5,6-dihydro-l,4-dimethyl-8- (4,4,5,5-tetramethyl-1.3.2- dioxaborolan-2-yl)-6-(4-cyano-phenyl) (270 mg, 0.61 mmol), 4-bromo-2- methyl-2H-1.2.3- triazole (109 mg, 0.67 mmol), tetrakis(triphenylphosphine)palladium(0) (70 mg) and potassium carbonate anhydrous (337 mg, 2.44 mmol) in tetrahydrofuran (10 mL) and water (2 mL) was reacted at 100 C for 30 minutes with microwave (pressure : 17.2 bar, equipment power : 150W). The reaction mixture was diluted with ethyl acetate (50 mL), washed by brine (20 mL x 3), dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated and the residue was purified by CombiFlash (silica gel, dichloromethane / methanol = 10:1) to afford 4H-[l,2,4]triazolo[4,3-a][l,5] benzodiazepine, 5,6-dihydro-l,4-dimethyl-8-(2-methyl-2H-l,2,3- triazole-4-yl)-6-(4-cyano-phenyl) as a white solid (65 mg, 27 % ).

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

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; HEWITT, Michael, C.; TAYLOR, Alexander, M.; HARMANGE, Jean-Christophe; WO2012/151512; (2012); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 6818-99-1, A common heterocyclic compound, 6818-99-1, name is 3-Chloro-1,2,4-triazole, molecular formula is C2H2ClN3, 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.

2.06 g (10 mmol) of 3-chloro-1,2,4-triazole was mixed with 20.6 ml of tetrahydrofuran, and 2.29 g (10 mmol) of pure 2-chloroisobutyryl chloride was added dropwise, over about 30 minutes. The mixture was stirred for 8 hours, filtered, the insoluble material was filtered off and the filtrate was concentrated to dryness under reduced pressure. 5 ml of methyl tert-butyl ether was added, stirred for 30 minutes, filtered, and the cake was dried to obtain 2.15g of product, yield 85%.

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; Ningbo Baisijia Pharmaceutical Technology Co., Ltd.; Jin Chunhua; Tang Jianbo; Wang Kedi; Zhu Qinfeng; (13 pag.)CN106866558; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics