Tag: M.W=0-100

Application of 60166-43-0, 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. 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

In a pressure vessel equipped with a magnetic stirring bar was added 3-bromo-7- chloro-5-((4,4-difluorocyclohexyl)(phenyl)methyl)-5H-pyrrolo[2,3-b:4,5-b’]dipyridine (240 mg, 0.489 mmol), l ,4-dimethyl-lH-l ,2,3-triazole (52.2 mg, 0.538 mmol) and DMF (5 mL). Tetramethylammonium acetate (98 mg, 0.734 mmol) and PdCl2(dppf)-CH2Cl2 adduct (28.0 mg, 0.034 mmol) was added. Argon was bubbled into the mixture with sonication for 5 min, then the vessel was capped, placed into a preheated aluminum block set at 100C and was stirred for 16 h. Solids were filtered, and the filtrate was purified by preparative HPLC (20-100% B; B solvent 90% MeCN/0.1% TFA water, Phenomenex LUNA C18 30xl00mm, 10 micron, 30 mL/min flow rate, 254nm UV; Rt = 1 1.6 min.). Like fractions were concentrated and re-purified by preparative HPLC: Column: Waters XBridge C 18, 19 x 200 mm, 5-mupiiota particles; Mobile Phase A: 5 :95 methanol: water with lOmM NH40Ac; Mobile Phase B: 95:5 methanol: water with lOmM NFLtOAc; Gradient: 40-80% B over 15 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 18 mg of a mixture of enantiomers. This material was subject to a chiral purification: Chiral SFC conditions: Chiralcel OJ-H preparative column, 30 x 250mm, 5muiotaeta; Mobile Phase: 15% methanol in CO2, 150 bar; Temp: 35C; Flow rate: 70.0 mL/min. for 25 min. ; UV monitored at 254nm; Injection: 0.25ml of ~9 mg/mL solution in MeOH (18 mg purified by stacked injection); Rt = isomer A: 13.8 min. ; isomer B: 18.3 min. Fractions containing the desired products were combined and dried via evaporation to give 6.9 mg (2%) of the isomer A with an average purity by LC/MS analysis was >99%. Fractions containing the desired products were combined and dried via evaporation to give 7.5 mg (3%) of the isomer B with an average purity by LC/MS analysis was >99%. Isomer A: Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7muetaiota particles; Mobile Phase A: 5:95 ACN:water with 10 mM NlrUOAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAc; Temperature: 50C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 1 mL/min; Detection: UV at 220 nm. Rt = 1.76 min.; LC/MS (M+H) = 568.7. Injection 2 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7-muetaiota particles; Mobile Phase A: 5:95 methanol: water with 10 mM NFL Ac; Mobile Phase B: 95:5 methanol: water with 10 mM NFL Ac; Temperature: 50C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 0.5 mL/min; Detection: UV at 220 nm. Rt= 2.77 min.; LC/MS (M+H) = 568.7. Isomer B: Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7mupiiota particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM MLtOAc; Temperature: 50C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 1 mL/min; Detection: UV at 220 nm. Rt= 1.86 min.; LC/MS (M+H) = 568.7. Injection 2 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7-mupiiota particles; Mobile Phase A: 5:95 methanol: water with 10 mM MLtOAc; Mobile Phase B: 95:5 methanol: water with 10 mM MLtOAc; Temperature: 50C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 0.5 mL/min; Detection: UV at 220 nm. Rt= 2.73 min.; LC/MS (M+H) = 568.7. NMR (500MHz, DMSO-c e) delta 8.82 (d, J=8.1 Hz, 1H), 8.67 (s, 1H), 8.54 (br. s., 1H), 7.73 (d, J=8.1 Hz, 3H), 7.32 (t, J=7.5 Hz, 2H), 7.25 (t, J=7.3 Hz, 1H), 6.09 (br. s., 1H), 4.36 (s, 3H), 4.02 (s, 3H), 3.52 (br. s., 1H), 2.30 (s, 3H), 2.07 (br. s., 1H), 1.92 (d, J=7.3 Hz, 1H), 1.82 (br. s., 1H), 1.73 (br. s., 1H), 1.66 (br. s., 1H), 1.45 (d, J=12.1 Hz, 1H), 1.37 (br. s., 1H), 1.30 (d, J=11.7 Hz, 1H). LC/MS (M+H) = 568.2; HPLC conditions: Rt= 0.93 min. (Column: Waters Aquity BEH C18 2.1 X 50 mm 1.7u; Mobile Phase A: water with 0.05% TFA; Mobile Phase B: ACN with 0.05% TFA; Temperature: 40C; Gradient: 2-98% B over 1.5 min; Flow: 0.8 mL/min).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature 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.

A mixture of 3 -methyl- IH-1, 2,4-triazole (2.20 g, 26.4 mmol), l,5-difluoro-2- methoxy-4-nitrobenzene (5.00 g, 26.4 mmol), and potassium carbonate (3.65 g, 26.4 mmol) in anhydrous DMSO (50 mL) was heated at 80 0C for 24 h. The reaction mixture was allowed to cool to rt and was poured into 500 mL of water/10 mL brine solution. The aqueous mixture was extracted with EtOAc (2 x 250 mL). The combined organic extracts were washed with water (500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude reaction mixture was purified using silica gel column chromatography (50% EtOAc/hexane) to afford l-(5-fluoro-2-methoxy-4-nitrophenyl)-3- methyl-lH-l,2,4-triazole (1.24 g, 18 % yield). LC-MS (M+H)+ = 253.2. 1H NMR (SOO MHz, CDCl3) delta ppm 8.95 (s, 1 H) 8.00 (d, J=I 1.60 Hz, 1 H) 7.80 (d, J=6.10 Hz, 1 H) 4.09 (s, 3 H) 2.50 (s, 3 H).

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; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, III, Lorin A.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2011/14535; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. Recommanded Product: 1-Methyl-1H-1,2,3-triazole

A solution of 1-methyl-1H-1, 2, 3-triazole (3.0 g, 36.1 mmol) in anhydrous THF (100 mL) was cooled to -78 , followed by the addition of butyllithium (15.89 mL, 39.7 mmol) dropwise to give a yellow suspension. The reaction mixture was stirred at -78 for 1 h before N-methoxy-N-methylacetamide (6.52 g, 63.2 mmol) was added. The white suspension was then allowed to warm to 10 and stirred for 16 h. The reaction was quenched with MeOH. This solution was purified by column chromatography on silica gel (petroleum ether /EtOAc 3: 1to 1: 1) to give the product as a solid.1H-NMR: (Chloroform-d400MHz) delta 8.16 (s, 1H) , 4.31 (s, 3H) , 2.58 (s, 3H)

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; ARASAPPAN, Ashok; BUNGARD, Christopher James; FRIE, Jessica L.; HAN, Yongxin; HOYT, Scott B.; MANLEY, Peter J.; MEISSNER, Robert S.; PERKINS, James; SEBHAT, Iyassu K.; WILKENING, Robert R.; (140 pag.)WO2016/29454; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 41253-21-8, 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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added 1,2,4-triazole sodium salt (6.3 g, 70 mmol) and the mixture stirred at 90 C. for 3 h after which the mixture was filtered and the solvent removed. The resulting residue was adsorbed onto silica gel and intermediates 67 and 68 separated by flash chromatography, eluting with 0% to 30% ethyl acetate/hexanes. Colorless needles (2.46 g, 18% yield) 1H NMR (500 MHz, CDCl3) ?: 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added 1,2,4-triazole sodium salt (6.3 g, 70 mmol) and the mixture stirred at 90 C. for 3 h after which the mixture was filtered and the solvent removed. The resulting residue was adsorbed onto silica gel and intermediates 67 and 68 separated by flash chromatography, eluting with 0% to 30% ethyl acetate/hexanes. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) ?: 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.

The chemical industry reduces the impact on the environment during synthesis Sodium 1,2,4-triazol-1-ide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (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. 288-88-0, name is 1H-1,2,4-Triazole, A new synthetic method of this compound is introduced below., Formula: C2H3N3

Intermediate 82: step a 4-(1H-1,2,4-triazol-1-yl)benzaldehyde 4- Fluorobenzaldehyde (12.0 mL, 1 12 mmol) was added dropwise by syringe to a stirring, heterogeneous mixture of 1,2,4-triazole (11.6 g, 168 mmol) and potassium carbonate (24.7 g, 179 mmol) in dimethyl formamide (220 mL) at 23 C. The mixture was heated to 105 C. After 3.5 hours, the mixture was allowed to cool to 23 C. The cooled solution was transferred to a 2 L Erlenmeyer flask and diluted with water (500 mL) and ethyl acetate ( 200 mL). The biphasic mixture was stirred until the layers cleanly separated. The layers were separated. The organic layer was washed with half-saturated aqueous sodium chloride solution (3 100 mL). The washed solution was dried with sodium sulfate, and the dried solution was filtered. The filtrate was concentrated to provide an off-white solid. The solid was suspended in a mixture of heptanes and isopropyl acetate (5: 1, 600 mL). The mixture was filtered and the filter cake was washed with heptanes-isopropyl acetate (5: 1). The solids were collected and dried under vacuum to afford the title compound as a white solid.

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; 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; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 41253-21-8,Some common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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.

1-2. Preparation of 1-(3-chloropropyl)-1,2,4-triazole (compound of formula 3) A 1,2,4-triazole sodium salt (5g, 54.91mmol) was dissolved in dimethylformamide (50mL) and the solution was cooled to 0. Then, sodium hydride (60%, 2.86g, 71.38mmol) was added thereto, followed by stirring for 30 minutes. 1-bromo-3-chloropropane (6.5mL, 65.89mmol) was added thereto, followed by stirring at room temperature for 12 hours, and the reaction was terminated with the addition of an ammonium chloride saturated solution. After extraction with ethyl acetate and water, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford the title compound (2.77g, 35%).1H NMR (CDCl3, 400MHz): delta 8.08 (s, 1H), 7.94 (s, 1H), 4.36 (t, J =6.4Hz, 2H), 3.45 (t, J =6Hz, 2H), 2.35-2.30 (m, 2H).

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

Reference:
Patent; DONG-A PHARM.CO., LTD.; KIM, Soon-Hoe; IM, Weon-Bin; CHOI, Sung-Hak; CHOI, Sun-Ho; SOHN, Ju-Hee; SUNG, Hyun-Jung; KIM, Mi-Yeon; CHO, Kang-Hun; SOHN, Tae-Kyoung; WO2011/132901; (2011); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 41253-21-8, 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 41253-21-8 as follows.

Intermediate 38: 4-Cyclohexyl-4- [ (1, 2, 4-triazol-1-yl) methyl] piperidine Step A: 1-BOC-4-Cyclohexyl-4- [ (1, 2, 4-triazol-1-yl) methyl] piperidine To a solution of 1-BOC-4-cyclohexyl-4- [ (methanesulfonyloxy) methyl] piperidine (375 mg, 1 mmol) in DMF (10 mL) was added Na-1, 2,4-triazole (273 mg, 3 mmol), and the solution was stirred at 90-100C for 12 h. After DMF was distilled off in vacuo, the reaction mixture was quenched wirh a saturated aqueous NH4C1 solution, and the organic material was extracted with EtOAc. The extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by column chromatography (eluent : acetone/DCM = 3/1) to give the title compound (313 mg, 90%). MS [M+H] = 349 (M+1)

According to the analysis of related databases, 41253-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG LIFE SCIENCES LTD.; YAMANOUCHI PHARMACEUTICAL CO., LTD.; WO2005/47253; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. category: Triazoles

To a mixture of l-fluoro-2-nitrobenzene (1 mL, 12.8 mmol, 1.0 equiv.) and 3-methyl- lH-l,2,4-triazole (1.27 g, 15.3 mmol, 1.2 equiv.) in acetonitrile (20 mL) was added potassium carbonate (5.29 g, 38.3 mmol, 3.0 equiv.) and the mixture was stirred at 60C for 12 hours. The mixture was cooled to 20C, diluted with ethyl acetate (20 mL) and filtered. The filtrate was concentrated under reduced pressure to give a residue which was purified by silica gel chromatography (petroleum ether: ethyl acetate 2: 1 to 1 : 1) to give the desired product as a light yellow solid (1.20 g, 46%); 1H NMR (DMSO-d6, 400 MHz) delta 8.96 (s, 1H), 8.12 (d, 71H), 7.90 – 7.88 (m, 1H), 7.86 – 7.84 (m, 1H), 7.60 (t, 7 = 8.0 Hz, 1H), 2.31 (s, 3H).

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

Reference:
Patent; SHIRE HUMAN GENETIC THERAPIES, INC.; MILLER, Thomas; PAPAIOANNOU, Nikolaos; (243 pag.)WO2018/144620; (2018); 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. 288-36-8, name is 1H-1,2,3-Triazole, A new synthetic method of this compound is introduced below., Product Details of 288-36-8

2-iodobenzoic acid (1 g, 4.03 mmol), 2H-l,2,3-triazole (0.334 g, 4.84 mmol), copper(I) iodide (0.768 g, 4.03 mmol), cesium carbonate (2.63 g, 8.06 mmol) were reacted in DMF at 120 C under microwave irradiation for 20 minutes. Then the reaction was monitored confirming the presence of the required product. Large amount of starting material resulted left. The reaction was further irradiated for 20 minutes at 120 C. Solvent was then removed under vacuum, poured into water (100 ml) and neutralised with 37% HC1. Aqueous phase was extracted with Et20 (3×100 ml), and the collected organic phases were concentrated to give 1 g of crude material. This was purified with Biotage SP1 (over a 340g C18 column) eluting with a gradient of ACN and water (modified with 0.5% HCOOH). Fractions were collected and concentrated under vacuum to give the title compound D43 as colourless solid (140 mg). UPLC (GEN QC Basic): rt = 0.29 minutes, peak observed: 188 (M-l) C9H7N302 requires: 189. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 6.47 (br. s., 1 H) 7.47 – 7.59 (m, 1 H) 7.66 (t, 1 H) 7.75 – 7.87 (m, 3 H) 7.91 (d, 1 H)

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

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89606; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7343-34-2, A common heterocyclic compound, 7343-34-2, name is 3,5-Dimethyl-4H-1,2,4-triazole, molecular formula is C4H7N3, 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: In a 10 mL round-bottomed flask, (2S,4R)-4-(2-chloro-4-fluorophenylsulfonyl)-N-(1- cyanocyclopropyl)- 1- (1- (trifluoromethyl)cyclopropanecarbonyl)pyffolidine-2-carboxamide (example 8b)) (400 mg, 788 imol, Eq: 1.00) was combined with DMA (5 mL) to give a colorless solution. 1H-1,2,4-triazole (111 mg, 1.58 mmol, Eq: 2.00) and cesium carbonate (513 mg, 1.58 mmol, Eq: 2.00) were added. The reaction mixture was heated to 80 ¡ãC and stilTed for 3h. The reaction mixture was poured into water and extracted with EtOAc (2x). The organic layers were combined, washed with saturated aqueous NaHCO3 solution (lx),water (3x) and brine (lx). The organic layers were dried over Na2SO4 and concentrated in vacuo.The crude material was purified twice by flash chromatography (silica gel, 20g, DCM/MeOH 98/2, 19/1) and (silica gel, 20g, Heptan/AcOEt 1/2, 1/3, 1/4) to yield the title compound as a white foam (264 mg; 60percent). :_Example 11 was obtained as a byproduct during the synthesis of example 10 as a white solid (34 mg; 7percent).

The synthetic route of 7343-34-2 has been constantly updated, and we look forward to future research findings.

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