Month: May 2021

Synthetic Route of 4928-87-4, These common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, 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: Single crystals of 1 were prepared by a branched tube method [34], 1H-1,2,4-triazole-3-carboxylic acid (0.117 g, 1 mmol), lead(II) nitrate (0.331 g, 1 mmol) and potassium bromide (0.119 g, 1 mmol) were placed in the bottom main of a branched tube. Water was carefully added to fill both arms, and then the arm to be heated was placed in oil bath at 60 C. After 7 days, colorless crystals were deposited in the cooler arm which were filtered off, washed with water and air dried. (0.225 g, yield 54%),

The synthetic route of 4928-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Safarifard, Vahid; Morsali, Ali; Inorganica Chimica Acta; vol. 405; (2013); p. 203 – 208;,
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

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 3179-31-5 as follows. name: 1H-1,2,4-Triazole-3-thiol

To a solution of 1-(benzenesulfonyloxyoctyl)-cyclopropene (480 mg, 1.55 mmol) in about 2 ml N,N-dimethylformamide was added potassium t-butoxide (19.8% in tetrahydrofuran, 734 mg, 1.55 mmol) and 1H-1,2,4-triazole-3-thiol (172 mg, 1.71 mmol.) After stirring at room temperature for about 2 hours, sodium iodide (87.7 mg, 0.775 mmol) was added. After the reaction was heated to about 50 C. for about 2 hours, water and ethyl acetate were added then the phases were separated. The isolated organic layer was washed twice with water, dried over magnesium sulfate and concentrated in vacuo. This residue was purified by column chromatography on silica gel using hexanes/ethyl acetate to give 30 mg of 70% pure 1-(1H-1,2,4-triazol-2-ylthiooctyl)-cyclopropene as an oil.

According to the analysis of related databases, 3179-31-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jacobson, Richard Martin; Kelly, Martha Jean; Wehmeyer, Fiona Linette; Evans, Karen Anderson; US2005/65033; (2005); 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. 202931-88-2, name is 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., Safety of 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (1.45 g, 3.37 mmol, Intermediate 5: step d) was added THF (25 mL) and the solution was cooled to -75 C. n-BuLi (2.5 M in hexanes, 1.3 mL, 3.25 mmol) was then added dropwise. After 2 minutes, 1-methyl-1H-1,2,3-triazole-5-carbaldehyde (580 mg, 5.22 mmol, in 3 mL THF) was introduced. The reaction mixture was allowed to warm to -20 C. over 45 minutes at which time the reaction was quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (5*40 mL) and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated to dryness. Chromatography on silica gel (5% CH3CN-DCM increasing to 30% CH3CN +2% MeOH) provided the title compound as an off white amorphous solid.

The synthetic route of 202931-88-2 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.; (53 pag.)US2017/258782; (2017); 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. 584-13-4, name is 4H-1,2,4-Triazol-4-amine, This compound has unique chemical properties. The synthetic route is as follows., category: Triazoles

3,5-bis(1-cyano-1-methylethyl) benzyl bromide obtained in Step IV (600 g, 1.965 mol) was heated with 4-amino-1,2,4-triazole (247.9 g, 2.948 mol) in isopropanol (4.5 L) for 7 to 7.5 hours at 80 C. to 85 C. The reaction mass was gradually cooled to 20 C. to 25 C. The reaction mass was stirred for 1 hour. The reaction mass was further cooled to 0 C. to 5 C., stirred for 2 hours, filtered, and washed with dichloromethane (2¡Á500 ml). The reaction mass was sucked dry. The dried cake was further dried at 40 C. to 45 C. under vacuum to obtained 2,2′-[5-(4-amino-1,2,4-triazolium-1-ylmethyl)-1,3-phenylene]di(2-methylpropio-nitrile)bromide (497.5 g, 65.0% yield). MP-198-203 C. IR (In cm-1, KBr): 3204, 3116, 3080, 2987, 2229, 1643, 1607, 1565, 1469, 1438, 1196, 1004 H1NMR (in CDCl3,delta (ppm)]: 10.31 (1H,s),9.20 (1H,s),7.66-7.63 (3H,s),6.984 (2H,s),5.657 (2H,s),1.71 ( 12H,s). M+[309] (free base)

According to the analysis of related databases, 584-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Glenmark Pharmaceuticals Limited; US2006/189670; (2006); 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 1001401-62-2,Some common heterocyclic compound, 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, molecular formula is C9H7N3O2, 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 6: (2-(2H-1 ,2,3-triazol-2-yl)phenyl)((2R,5R)-5-hydroxy-2-methylpiperidin-1-yl)methanone (6) A solution of (3R, 6R)-6-methylpiperidin-3-ol (5.31 g, 46.1 mmol), 2-(2H-1,2,3- triazol-2-yl)benzoic acid (10.5 g, 55.3 mmol), EDC (17.7 g, 92.0 mmol), 1-hydroxy-7- 30 azabenzotriazole (12.6 g, 92.0 mmol), triethylamine (19.3 mL, 138 mmol) in DMF (300 mL) was stirred at 50 C overnight, then diluted with saturated aqueous sodium bicarbonate and extracted 3x with ethyl acetate. The organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel gradient chromatography (0-100% ethyl acetate in hexanes), providing the titled compound as a pale yellow solid. LRMS m/z (M+H) 287.3 found, 287.1 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/88864; (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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C2H5N5

Example 142-Amino-5-cyclopropyl-6- [(3,4-dichlorophenyl)methyl] -4H- [ 1 ,2,4] triazolo [5,1- b] pyrimidin-7-oneEthyl 3-cyclopropyl-2-[(3,4-dichlorophenyl)methyl]-3-oxo-propanoate (200 mg, 634.5 mmol, Method II) and lH-l,2,4-triazole-3,5-diamine (57.2 mg, 577 mmol) were added to tri-n-butylamine (228 mu) and the resulting mixture stirred at 160 ¡ãC for 48 h. The mixture was evaporated and the residue recrystallised from isopropanol to give the title compound (43 mg, 21percent) as a white solid.1H NMR (400.13 MHz, DMSO-d6) delta 0.90-1.05 (4H, m), 2.05-2.17 (1H, m), 4.00 (2H, s), 6.25 (2H, br s), 7.28 (1H, d), 7.52 (2H, d), 12.20 (1H, br s); m/z (ES) (M+H)+ = 350.

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 1455-77-2.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BENGTSSON, Boel, Ase; BLACKABY, Wesley; CUMMING, John; FAULL, Alan, Wellington; LARSSON, Joakim; NASH, Ian, Alun; OLDHAM, Keith; PAPE, Andrew; WO2011/114148; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 61-82-5,Some common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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.

Add 1.0 mmol of p-nitrobenzaldehyde, 1.0 mmol of ethyl acetoacetate, 1.0 mmol of 3-amino-1,2,4-triazole, and 0.18 g of magnetic nanosulfonic acid to 9 ml of ethanol-dimethylformamide, respectively. In an aqueous solution (V (ethanol): V (dimethylformamide): V (water) = 7: 2: 1) in a 50 ml three-necked flask with a stirrer and a condenser tube, stir well at room temperature. Heating to 86 C for 146min, TLC (thin plate chromatography) detection, raw material spots disappeared, magnetic nanosulfonic acid catalyst was adsorbed with a magnet while hot, the remaining reaction solution was cooled to room temperature, a large amount of solids were precipitated, the solids were crushed, and left to stand , Suction filtration, the obtained filter residue was washed with ethanol and vacuum-dried to obtain 7- (4-nitrophenyl) -5-methyl-4,7-dihydro- [1,2,4] triazolo [1, 5-a] Pyrimidine-6-carboxylic acid ethyl ester, the purity by liquid chromatography was 99.1%, and the calculated purity was 83%. The adsorbed magnetic nanosulfonic acid was put into the filtrate after suction filtration without any treatment, and p-nitrobenzaldehyde, ethyl acetoacetate, and 3-amino-1,2,4-triazole were directly added for repeated use.

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-Triazol-5-amine, its application will become more common.

Reference:
Patent; Ma’anshan Tai Bo Chemical Technology Co., Ltd.; Lu Hua; Shen Jianzhong; (11 pag.)CN110540540; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

G. (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid 2-methanesulfonyl-ethyl ester (R4=H; R7=-(CH2)2-SO2CH3) (2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid (207 mg, 501 mumol, 1.0 eq.), HOBt (0.2 g, 1.5 mmol, 3.0 eq.), and EDCI (260 muL, 3.0 eq.) were dissolved in DCM (4 mL). After stirring for 2 minutes, 2-(methylsulfonyl)ethanol (0.5 g, 4.0 mmol, 8.0 eq.) and 4-methylmorpholine (220 muL) were added. The mixture was stirred at room temperature for 2 hours. The reaction was quenched with water. The DCM layer was separated and concentrated, then purified by flash chromatography (10-100% EtOAc/hexanes). MeCN (2 mL) and 4 M of HCl in dioxane (0.5 mL) were added and the resulting mixture was stirred at room temperature for 1 hour. The solvent was removed to provide the intermediate HCl salt, which was used in the following coupling step. 1,2,3-Triazole-4-carboxylic acid (56.6 mg, 501 mumol, 1.0 eq.), HATU (190 mg, 501 mumol, 1.0 eq.) were dissolved in DMF (1 mL) and the resulting solution was stirred for 5 minutes, followed by the addition of DIPEA (262 muL) and the intermediate HCl salt. After 10 minutes, the reaction was quenched with AcOH and the product was purified by preparative HPLC to yield the title compound (28 mg; purity 95%). MS m/z [M+H]+ calc’d for C25H30N4O6S, 515.19. found 515.4.

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, 1H-[1,2,3]Triazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics