Day: May 18, 2021

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

Application of 49607-51-4,Some common heterocyclic compound, 49607-51-4, name is 1-Methyl-1H-1,2,4-triazol-3-amine, molecular formula is C3H6N4, 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: 5 ml of toluene were added to 100 mg (0.22 mmol) of 5-[4-chloro-3-(trifluoromethyl)phenoxy]-2-(methylsulphonyl)-6-(trifluoromethyl)pyrimidin-4(3H)-one (Example 40A) and 57 mg (0.67 mmol) of 4-amino-1H-pyrazole, and the mixture was then re-concentrated under reduced pressure. A drop of DMSO was added to the residue, and the mixture was then stirred at 150° C. for 1 h. The mixture was then purified directly by preparative HPLC [column: Chromatorex C18 10 mum, 250×30 mm; flow rate: 50 ml/min; run time: 45 min; detection: 210 nm; injection after 3 min of run time; mobile phase A: acetonitrile, mobile phase B: water; gradient: 10percent A (5.00 min)?95percent A (35.00-40.00 min)?10percent A (40.50-45.00 min)]. This gave 30 mg (31percent of theory) of the title compound.The Exemplary compounds below were prepared analogously to Example 104 from the appropriate 2-methylsulphonyl-substituted pyrimidinones and the respective amine components:(20percent of theory; without addition of DMSO)

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; STRAUB, ALEXANDER; COLLIN, MARIE-PIERRE; KOCH, MICHAEL; MEYER-KIRCHRATH, JUTTA; SCHLEMMER, KARL-HEINZ; NISING, CARL FRIEDRICH; BIBER, NICOLE; ANLAUF, SONJA; GROMOV, ALEXEY; WITTWER, MATTHIAS BEAT; (392 pag.)TW2016/5831; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 184177-83-1, A common heterocyclic compound, 184177-83-1, name is 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one, molecular formula is C30H35N5O3, 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.

In a dry 300 L reactor, 70 kg of tetrahydrofuran was added under vacuum. The mixture was stirred, and after nitrogen replacement, the temperature was lowered to -10 C, and then 0.6 kg of sodium hydride was added in portions under nitrogen protection, and after stirring for 0.5 h, Continue to control the temperature T ? -10 C to add 12 kg of POB/24 kg of tetrahydrofuran solution to the system, After the dropwise addition, the mixture was stirred for 1 hour. Add 10 kg of POA/20 kg of tetrahydrofuran solution to the system. The reaction was carried out at a temperature of -10 to 0 C, and the monitoring until the POA disappeared. The temperature was controlled by T ? -10 C, and 1 kg of methanol was added dropwise. After stirring for 0.5 h, the reaction was quenched by adding 1 kg of water. Temperature control T ? 40 C under reduced pressure to concentrate about 70 L of tetrahydrofuran, Add 200 kg of dichloromethane and wash with 50 kg * 3 tap water. Wash with 50 kg of saturated brine, and dry the organic phase with 10 kg of anhydrous sodium sulfate. Filtration, temperature control T ? 40 C, concentrated under reduced pressure to no fraction, 60 kg of ethyl acetate was added while hot, and the temperature was raised to 70 C for 1 h. Then, the temperature is lowered to 0 to 10 C at a rate of 10 C / h, and suction filtration is performed. The filter cake was rinsed with pre-cooled 5 kg of ethyl acetate and drained. Transfer to the drying room at 40 ~ 45 C under reduced pressure for 40h, Received 19.2 kg of POC.

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; Borui Bio-pharmaceutical Taixing Co., Ltd.; Yuan Jiandong; Fu Xinliang; Cong Qilei; Xing Xiaopei; (14 pag.)CN109796446; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference 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.

General procedure: A suspension of 3,5-diamino-1,2,4-triazole (0.1 g, 1 mmol) in absolute EtOH (10 mL) was added to a stirring solution of azo-coupled precursors, Ia-IVa, (2 mmol) in absolute EtOH (50 mL) during a period of 10 min at 60-70 °C. The mixture was heated in water bath for 15 h at 80 °C with stirring. The mixture was filtered whilst hot and the obtained solid was washed with hot ethanol (three time) and then with diethylether. The resulted product was dried in air.

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; Khanmohammadi, Hamid; Erfantalab, Malihe; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 86; (2012); p. 39 – 43;,
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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., SDS of cas: 4928-87-4

Example 59 1-(2-tert-Butylphenyl)-4-(1H-1,2,4-triazol-3-ylcarbonyl)piperazine A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (0.30 g, 1.03 mmol), 1,2,4-triazole-3-carboxylic acid (0.12 g, 1.08 mmol), triethylamine (0.22 g, 2.16 mmol), EDCI (0.21 g, 1.08 mmol) and HOBt (0.17 g, 1.08 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between ethyl acetate and water, and the suspension of white precipitate in ethyl acetate was washed with 10% sodium hydrogen carbonate solution, water, saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford white solid. This solid was triturated with diisopropyl ether to give the title compound (0.18 g, 56%) as a white solid, mp 295 C. 1H NMR (300 MHz, DMSO-d6) delta 1.42 (s, 9H), 2.63-3.11 (m, 5H), 3.18-3.47 (m, 1H), 4.38-4.79 (m, 2H), 7.02-7.29 (m, 2H), 7.28-7.47 (m, 2H), 8.46 (s, 1H), 14.46 (br. s., 1H). LC/MS (ESI+) m/z: 313 (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; Kasai, Shizuo; McGee, JR., Kevin Francis; US2012/71489; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 118863-62-0, These common heterocyclic compound, 118863-62-0, name is 3-(4-Bromophenyl)-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.

Step 1: 3-(4-Bromophenyl)-1-(4-methoxybenzyl)-1H-1,2,4-triazole A mixture of 3-(4-bromophenyl)-1H-1,2,4-triazole (5 g, 22.3 mmol), 1-(chloromethyl)-4-methoxybenzene (4.19 g, 26.8 mmol) and cesium carbonate (14.6 g, 44.9 mmol) in DMF (100 mL) was stirred at room temperature for 16 h. The resulting solution was diluted with water and extracted with ethyl acetate. The organic layers were combined and concentrated in vacuo. The crude product was purified via flash chromatography on silica gel (solvent gradient, 0-5% ethyl acetate in petroleum ether) to yield 6 g (78%) of the title compound as a white solid. LCMS (ESI): [M+H]+=344/346.

Statistics shows that 3-(4-Bromophenyl)-1H-[1,2,4]triazole is playing an increasingly important role. we look forward to future research findings about 118863-62-0.

Reference:
Patent; Genentech, Inc.; Braun, Marie-Gabrielle; Garland, Keira; Hanan, Emily; Purkey, Hans; Staben, Steven T.; Heald, Robert Andrew; Knight, Jamie; Macleod, Calum; Lu, Aijun; Wu, Guosheng; Yeap, Siew Kuen; (183 pag.)US2018/65983; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4923-01-7, A common heterocyclic compound, 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, molecular formula is C3H6N4, 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: 3-Amino-1,2,4-triazole 8a-f (1.0 mmol), o-hydroxybenzaldehyde9a-e (1.0 mmol), acetone (10) (0.22 ml,3.0 mmol), and abs. EtOH (2 ml) were mixed in amicrowave process vial, and then 4 N solution of HCl indioxane (0.07 ml, 0.3 mmol) was added. The mixture wasirradiated at 150C for 30 min. The reaction mixture wascooled by an air flow and stirred for 24 h at roomtemperature for complete precipitation of the product. Theprecipitate was filtered off, washed with EtOH (1 ml) andEt2O (3×1 ml), and dried. Compounds 1a-w were obtainedin a form of white solids.

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:
Article; Guemue?, Mustafa K.; Gorobets, Nikolay Yu.; Sedash, Yuriy V.; Chebanov, Valentin A.; Desenko, Sergey M.; Chemistry of Heterocyclic Compounds; vol. 53; 11; (2017); p. 1261 – 1267; Khim. Geterotsikl. Soedin.; vol. 53; 11; (2017); p. 1261 – 1267,7;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 6523-49-5, 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. 6523-49-5 name is 4-(1,2,4-Triazol-1-yl)aniline, 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.

Title Compound 300 mg of the product, 7A, was dissolved in THF and 0.15 g of Intermediate 45B and 0.1 ml of pyridine were added. The mixture was refluxed for 3 hours, then dilute HCl was added. A precipitate was obtained which was filtered and washed with acetone to give 200 mg of an off-white product. Microanalysis: theory(%, 1 H20): C, 50.5; H, 3.00; N, 17.1; obtained (%): C, 50.5; H, 2.80; N, 16.9.

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; Sartori, Eric; Maillet, Magali; Paugam, Marie France; Nicolai, Eric; Lawrence, Michael; US2005/143384; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-65-5, 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

A solution of 1-methyl-1H-1,2,3-triazole (0.954 g, 11.4 mmol, prepared according to PCT Int. Appl., 2008098104) in THF (22 mL) was stirred at ?-70 C. under argon while n-BuLi (2.56 M in hexanes; 4.29 mL, 11.0 mmol) was added dropwise over 5 minutes. After stirring for another 5 minutes, a solution of ethyl methoxy(methyl)carbamate (0.665 g, 4.99 mmol) (Aldrich) in THF (3 mL) was added dropwise over 5 minutes. After stirring at ?-70 C. for an additional 5 minutes, the cold bath was removed and the light slurry was allowed to warm to room temperature with stirring for 1 hour 20 minutes. The reaction was then quenched at room temperature with 5 M aqueous NH4Cl (3 mL) and the aqueous layer was extracted with THF (1*6 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. A portion of the residue was crystallized from ?30 mL toluene to provide, after washing the filter cake with ether (1*3 mL) and heptane (1*3 mL), the title compound as blunt needles.

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, 1-Methyl-1H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); 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.

EXAMPLE 1 2-(((3R,6R)-l-(2-(2H-l,2,3-Triazol-2-yl)benzoyl)-6-methylpiperidin-3- yl)amino)isonicotinonitrile Step 1: (2R,55′)-Benzyl 2-methyl-5-((methylsulfonyl)oxy)piperidine-l-carboxylate (2) A solution of (2R,55)-benzyl 5-hydroxy-2-methylpiperidine-l-carboxylate (15.0 g, 60.2 mmol), 4-dimethylamino pyridine (0.74 g, 6.0 mmol), and (( (401 mL) was treated with DIEA (15.8 mL, 90.0 mmol) and cooled at 0 C. Methanesulfonyl chloride (5.9 mL, 75 mmol) in (( (67 mL) was added dropwise and stirring continued at 0 C for 2 h. The reaction was diluted with water and 1 N HQ and the separated organics were washed with brine, dried over MgS04, filtered, concentrated and dried, providing the crude title compound which was used without further purification. LRMS m/z (M+H) 328.3 found, 328.1 required. Step 2: (2R,5R)-Benzyl 5-azido-2-methylpiperidine-l-carboxylate (3) A solution of crude (2R,55)-benzyl 2-methyl-5-((methylsulfonyl)oxy)piperidine- 1 -carboxylate (19.7 g, 60.2 mmol) and sodium azide (6.65 g, 102 mmol) in DMF (86 mL) was heated to 85 C overnight. The reaction was diluted with EtOAc, washed 2x with water, lx with brine, dried over magnesium sulfate, filtered, and concentrated, providing the crude title compound which was used without further purification. LRMS m/z (M+H) 275.3 found, 275.2 required. Step 3: (2R,5R)-Benzyl 5-amino-2-methylpiperidine-l -carboxylate (4) To a solution of (2R,5R)-benzyl 5-azido-2-methylpiperidine-l-carboxylate (15.2 g, 55.4 mmol) in THF (111 mL) was added trimethylphosphine (1.0 M in toluene, 55.4 mL, 55.4 mmol) dropwise over 20 min. The reaction was quenched with water (30 mL) and stirred at RT overnight. The mixture was diluted with dichloromethane, washed 2x with water, lx with brine, dried over magnesium sulfate, filtered, and concentrated, providing the crude title compound as an orange oil which was used without further purification. LRMS m/z (M+H) 249.6 found, 249.3 required. Step 4: (2R,5R)-Benzyl-5-((?ert-butoxycarbonyl)amino-2-methylpiperidine-l-carboxylate (5) A solution of (2R,5R)-Benzyl 5-amino-2-methylpiperidine-l-carboxylate (3.08 g, 12.4 mmol) and 4-dimethylaminopyridine (0.015 g, 0.12 mmol) in dichloromethane (62 mL) was treated with a solution of di-tert-butyl dicarbonate (2.91 mL, 12.5 mmol) in dichloromethane (20 mL) dropwise and stirred at RT overnight. The reaction was concentrated in vacuo, providing the crude title compound which was used without further purification. LRMS m/z (M+H) 349.4 found, 349.3 required. Step 5: tert-Butyl ((3R,6R)-6-methylpiperidin-3-yl)carbamate (6) A solution of (2R,5R)-benzyl-5-((/er/-butoxycarbonyl)amino-2-methylpiperidine- 1 -carboxylate (4.32 g, 12.4 mmol) and palladium (10 wt % on activated carbon, 0.300 g, 2.82 mmol) in degassed ethanol (100 mL) and methanol (5 mL) was stirred for 72 h under an atmosphere of hydrogen gas. Additional palladium (10 wt % on activated carbon, 0.10 g, 0.94 mmol) was added, and the reaction was recharged with hydrogen gas and allowed to stir at RT overnight. The degassed mixture was then filtered over celite, washing with EtOH. The filtrate was concentrated to give the titled compound as a crude, light yellow solid which was used without further purification. Step 6: tert-Butyl((3R,6R)-l-(2-(2H-l,2,3-triazol-2-yl)benzoyl)-6-methylpiperidin-3- yl)carbamate (7) A solution of 2-(2H- 1,2,3 -triazol-2-yl)benzoic acid (4.24 g, 22.40 mmol), tert- butyl ((3R,6R)-6-methylpiperidin-3-yl)carbamate (3.20 g, 14.93 mmol), l-hydroxy-7- azabenzotriazole (4.06 g, 29.9 mmol), EDC (5.72 g, 29.9 mmol), and DIEA (15.65 mL, 90 mmol) in DMF (100 mL) was heated at 50 C overnight. The reaction was diluted with saturated, aqu. aHC03 and extracted 2x with EtOAc. The organics were washed with brine, dried over MgS04, filtered, and concentrated. The residue was purified by silica gel gradient chromatography (0-80% EtOAc in hexanes), providing the title compound. LRMS m z (M+H) 386.4 found, 386.2 required. Step 7: (2-(2H-l,2,3-Triazol-2-yl)phenyl)((2R,5R)-5-amino-2-methylpiperidin-l-yl)methanone (8) A solution of tert-butyl((3R,6R)-l-(2-(2H-l,2,3-triazol-2-yl)benzoyl)-6- methylpiperidin-3-yl)carbamate (3.6 g, 9.3 mmol) in EtOAc (78 mL) was saturated with HC1 (g) and stirred for 2 h. The reaction was concentrated and the residue basified with 1 N NaOH. The mixture was extracted 3x with EtOAc, then the organics were washed with brine, dried over MgS04, filtered, and concentrated. The residue was purified by silica gel gradient chromatography (0-20% MeOH in CH2C12), providing the title compound. LRMS m/z (M+H) 286.3 found, 286.3 required. Step 8: 2-(((3R,6R)-l-(2-(2H- 1,2,3 -triazol-2-yl)benzoyl)-6-methylpiperidin-3- yl)amino)isonicotinonitrile A solution of (2-(2H-l,2,3-triazol-2-yl)phenyl)((2R,5R)-5-amino-2- methylpiperidin- 1 -yl)methanone (400 mg, 1.40 mmol) 2-fluoroisonicotinonitrile (342 mg, 2.80 mmol), and cesium carbonate (776 mg, 2.383 mmol) in DMSO (4673 muKappa) was heated at 50 C for 48 h. The reaction was cooled, dilut…

The synthetic route of 1001401-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2014/85208; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics