Day: March 5, 2021

Adding a certain compound to certain chemical reactions, such as: 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, 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 27996-86-7, COA of Formula: C9H7N3O

A mixture of alpha ionone (1.152 g, 1.23 ml, 6 mmol), 4-(1H-1,2,4-triazol-1-yl) benzaldehydes (0.865 g, 5 mmol), cetyltrimethyl ammonium bromide (0.070 g, 0.5 mmol), sodium hydroxide (0.600 g, 15 mmol) and water (25 ml) was stirred at room temperature for 24 h. Reaction progress was monitored by TLC and compound was extracted with ethyl acetate (2 ¡Á 50 ml). The combined organic extract was washed with water (2 ¡Á 50 ml), brine solution (50 ml), dried (Na2SO4) and the solvent was removed in vacuum. The crude product was purified by column chromatography (SiO2, 60-120 mesh). Elution with 10 % ethyl acetate in hexane furnished a pale yellow coloured solid (0.400g, 23%). Mp: 108-110OC; IR (KBr, cm-1): 2915, 1651 (C=O), 1598 (C=N); 1H NMR (CDCl3, 300 MHz): delta 0.88 (s, 3H), 0.95 (s, 3H), 1.22-1.29 (m, 1H), 1.43-1.52 (m, 1H), 1.60 (s, 3H), 2.07 (brs, 2H), 2.36 (d, J = 9 Hz, 1H), 5.53 (brs, 1H), 6.39 (d, J = 16 Hz, 1H), 6.85 (dd, J = 16, 9 Hz, 1H), 7.01 (d, J = 16 Hz, 1H), 7.63-7.74 (m, 5H), 8.11 (s, 1H), 8.60 (s, 1H); 13C NMR (CDCl3, 75 MHz): delta 22.92, 23.10, 26.90, 27.95, 31.25, 32.75, 54.67, 2¡Á120.13, 122.83, 125.72, 2¡Á129.72, 130.54, 131.93, 134.81, 137.99, 140.89, 141.16, 149.44, 152.81, 188.53; ESI-MS m/z: 348 [M+1]+; Analysis calculated for C22H25N3O: C, 76.05; H, 7.25; N, 12.09; Found: C, 76.05; H, 7.29; N, 12.03.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Suryawanshi; Tiwari, Avinash; Kumar, Santosh; Shivahare, Rahul; Mittal, Monika; Kant, Padam; Gupta, Suman; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2925 – 2928;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, 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. Safety of 4-[1,2,4]Triazol-1-yl-benzaldehyde

A mixture of beta ionone (0.48 g, 0.507 ml, 2.5 mmol), 4-(1H-1,2,4-triazol-1-yl) benzaldehydes (0.346 g, 2 mmol), cetyltrimethyl ammonium bromide (0.028 g, 0.20 mmol), sodium hydroxide (0.240 g, 6 mmol) and water (10 ml) was stirred at room temperature for 24 h. Reaction progress was monitored by TLC and compound was extracted with ethyl acetate (2 ¡Á 30 ml). The combined organic extract was washed with water (2 ¡Á 30 ml), brine solution (25 ml), dried (Na2SO4) and the solvent was removed in vacuum. The crude product was purified by column chromatography (SiO2, 60-120 mesh). Elution with 10 % ethyl acetate in hexane furnished a yellow coloured solid (0.164 g, 24%). Mp: 103-104OC; IR (KBr, cm-1): 2929, 1643 (C=O), 1590 (C=N); 1H NMR (CDCl3, 300 MHz): delta 1.05 (s, 6 H, CH3-8? and CH3-9?), 1.41-1.45 (m, 2H, CH2-5?), 1.55-1.61 (m, 2H, CH2-4?), 1.77 (s, 3H, CH3-7?), 2.04 (t, J = 6 Hz, 2 H, H-3?), 6.42 (d, J = 16 Hz, 1H, H-4), 6.96 (d, J = 16 Hz, 1H, H-2), 7.48 (d, J = 16 Hz, 1H, H-5), 7.61 (d, J = 16 Hz, 1H, H-1), 7.67 (brs, 4H, H-2?, H-3?, H-5? and H-6?), 8.06 (s, 1H, H-3???), 8.55 (s, 1H, H-5???); 13C NMR (CDCl3, 75 MHz): delta 18.86, 21.89, 2¡Á28.87, 33.76, 34.18, 39.85, 2¡Á120.08, 126.64, 129.35, 2¡Á129.63, 134.87, 136.50, 137.26, 137.89, 140.69, 140.82, 143.54, 152.78, 188.66; ESI-MS m/z: 348 [M+1]+; Analysis calculated for C22H25N3O: C, 76.05; H, 7.25; N, 12.09; Found: C, 76.10; H, 7.19; N, 12.11.

The synthetic route of 4-[1,2,4]Triazol-1-yl-benzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Suryawanshi; Tiwari, Avinash; Kumar, Santosh; Shivahare, Rahul; Mittal, Monika; Kant, Padam; Gupta, Suman; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2925 – 2928;,
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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Product Details of 16681-65-5

n-BuLi (1.23 M in hexanes, 1.1 mL, 1.35 mmol) was added dropwise to a stirred slurry of 1-methyl-1,2,3-triazole (112 mg, 1.35 mmol) in THF (1 mL) at -40 C. under nitrogen. After stirring for another 30 minutes, the mixture was treated dropwise with a solution of (4-chloro-3-isopropoxy-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (252 mg, 0.67 mmol, Intermediate 27) in THF (5 mL). The reaction was allowed to warm to room temperature over 1 hour. The reaction was then quenched with saturated aqueous NH4Cl. The mixture was poured into a separatory funnel and extracted with DCM (4*60 mL). The organics were combined, washed with brine, dried (Na2SO4), filtered and concentrated to dryness to afford a light yellow oil. The crude material was purified by FCC (1-7.5% MeOH/DCM) followed by reverse-phase HPLC (acetonitrile/water+NH4OH) to provide the title compound as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.08 (d, J=2.2 Hz, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.33 (dd, J=8.6, 2.2 Hz, 1H), 7.18 (s, 1H), 6.18 (s, 1H), 4.74-4.67 (m, 1H), 4.32 (s, 1H), 4.13 (s, 3H), 3.94 (s, 3H), 3.39 (s, 3H), 2.32 (s, 3H), 1.39 (d, J=6.2 Hz, 6H). MS (ESI): mass calcd. for C22H25ClN6O3, 456.2. m/z found, 457.0 [M+H]+. [4-Chloro-2-methoxy-3-(1-methylethoxyl)quinolin-6-yl](1,2-dimethyl-1H-imidazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol was purified by chiral SFC (Stationary phase: CHIRALPAK AD-H 5 muM 250*20 mm, Mobile phase: 70% CO2, 30% MeOH/iPrOH 50/50 v/v+(0.3% iPrNH2)) to give 2 enantiomers. The first eluting enantiomer was Example 80b: 1H NMR (400 MHz, CDCl3) delta ppm 8.09 (d, J=2.2 Hz, 1H), 7.77 (d, J=8.7 Hz, 1H), 7.32 (dd, J=8.7, 2.2 Hz, 1H), 7.17 (s, 1H), 6.17 (s, 1H), 4.75-4.66 (m, 1H), 4.36 (s, 1H), 4.13 (s, 3H), 3.94 (s, 3H), 3.39 (s, 3H), 2.32 (s, 3H), 1.39 (d, J=6.2 Hz, 6H). MS (ESI): mass calcd. for C22H25ClN6O3, 456.2. m/z found, 457.2 [M+H]+ and the second eluting enantiomer was Example 80c: 1H NMR (400 MHz, CDCl3) delta ppm 8.06 (d, J=2.2 Hz, 1H), 7.80 (d, J=8.7 Hz, 1H), 7.35-7.32 (m, 1H), 7.21 (s, 1H), 6.24 (s, 1H), 4.74-4.67 (m, 1H), 4.13 (s, 3H), 3.95 (s, 3H), 3.52 (s, 1H), 3.42 (s, 3H), 2.37 (s, 3H), 1.39 (d, J=6.2 Hz, 6H). MS (ESI): mass calcd. for C22H25ClN6O3, 456.2. m/z found, 457.2 [M+H]+.

The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JOHNSON & JOHNSON; 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.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, 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. 16681-70-2 name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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.

[0760] lH-1,2,3-triazole-4-carboxylic acid (2.6 mg, 23f.tmol) was combined with HATU (9.6 mg, 25 flillOl) in DMF(3.0 mL) and stirred at room temperature for 15 minutes.Compound 2 (13 mg, 29 f.tmol) was dissolved in DIPEA (12f.LL, 69 f.tmol) and combined with the activated acid solution.The mixture was stirred at room temperature for 15 minutes,after which time LCMS indicated desired product formation.The solvent was removed in vacuo and the crude residue waspurified by reverse phase chromatography to yield Compoundb (0.8 mg) as a TFA salt. MS m/z [M+Ht calc’d forC25H27ClF3N50 3 , 538.18. found 538.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-[1,2,3]Triazole-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 13273-53-5, A common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, 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. (S)-(6-bromo-5-(2,5-difluoro-4-nitrophenoxy)-2-methyl-3,4-dihydroquinoliii-l(2H)- yl)(cyclopropyl)methanone and (S)-(6-bromo-5-(4,5-difluoro-2-nitrophenoxy)-2-methyl-3,4- dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone [0568] A 100-mL, 3-necked round-bottom flask was charged with a solution of (S)-(6-bromo-5- hydroxy-2-methyl-3,4-dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone (2.00 g, 6.45 mmol) in tetrahydrofuran (20 mL). Potassium tert-butoxide (0.797 g, 7.10 mmol) was added in portions at 0 C and the mixture stirred for 5 minutes. 1 ,2,4-Trifluoro-5-nitrobenzene (1.72 g, 9.71 mmol) was then added, and the resulting mixture stirred at 0 C for 3 h. Hydrochloric acid (I aqueous, 10 mL) was added, and the aqueous phase was separated and extracted with ethyl acetate (2 x 15 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 1 : 10, ethyl acetate/petroleum ether) to afford a mixture of (S)-(6-bromo-5-(2,5-difluoro-4-nitrophenoxy)-2- methyl-3,4-dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone and (S)-(6-bromo-5-(4,5-difluoro-2- nitrophenoxy)-2-methyl-3,4-dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone (2.1 g, 70%) as yellow oil. MS (ESI, pos. ion) m/z 467,469[M+H]+ Step 2. (S)-(5-(4-amino-2,5-difluorophenoxy)-6-bromo-2-methyl-3,4-dihydroquinoliii-l(2H)- yl)(cyclopropyl)methanone and (S)-(5-(2-amino-4,5-difluorophenoxy)-6-bromo-2-methyl-3,4- dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone [0569] A 100-mL, round-bottom flask was charged with a mixture of (S)-(6-bromo-5-(2,5-difiuoro- 4-nitrophenoxy)-2-methyl-3,4-dihydroquinolin- 1 (2H)-yl)(cyclopropyl)methanone and (S)-(6- bromo-5-(4,5-difiuoro-2-nitrophenoxy)-2-methyl-3,4-dihydroquinolin-l(2H)- yl)(cyclopropyl)methanone (2.1 g, 4.49 mmol), iron powder (1.26 g, 22.5 mmol), ammonium chloride (0.476 g, 8.90 mmol), tetrahydrofuran (10 mL), ethanol (10 mL), and water (3 mL). The resulting mixture stirred overnight at 80 C. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was extracted with ethyl acetate (2 x 15 mL). The combined organic layers were concentrated under vacuum to afford a mixture of (S)-(5-(4-amino-2,5- difluorophenoxy)-6-bromo-2-methyl-3,4-dihydroquinolin- 1 (2H)-yl)(cyclopropyl)methanone and (S)-(5-(2-amino-4,5-difluorophenoxy)-6-bromo-2-methyl-3,4-dihydroquinolin-l(2H)- yl)(cyclopropyl)methanone (1.8 g, 96%) as brown oil, which was directly used in next step without further purification. MS (ESI, pos. ion) m/z 437,439[M+H]+ Step 3. (S)-(6-bromo-5-(3,4-difluorophenoxy)-2-methyl-3,4-dihydroquinolin-l(2H)- yl)(cyclopropyl)methanone and (S)-(6-bromo-5-(2,5-difluorophenoxy)-2-methyl-3,4- dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone [0570] A 100-mL, round-bottom flask was charged with a mixture of (S)-(5-(2-amino-4,5- difluorophenoxy)-6-bromo-2-methyl-3,4-dihydroquinolin- 1 (2H)-yl)(cyclopropyl)methanone and (S)-(5-(4-amino-2,5-difluorophenoxy)-6-bromo-2-methyl-3,4-dihydroquinolin-l(2H)- yl)(cyclopropyl)methanone (1.8 g, 4.12 mmol) and N,N-dimethylformamide (10 mL). A solution of tert-butyl nitrite (1.2 g, 11.64 mmol) in N,N-dimethylformamide (10 mL) was added dropwise, and the resulting solution stirred for 4 h at 50 C. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (100 mL). The organic layer was washed with water (3 x 20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 1 : 10, ethyl acetate/petroleum ether) to afford a mixture of (S)-(6-bromo-5-(3,4-difluorophenoxy)-2-methyl-3,4- dihydroquinolin- 1 (2H)-yl)(cyclopropyl)methanone and (S)-(6-bromo-5-(2,5-difluorophenoxy)-2- methyl-3,4-dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone (0.600 g, 35%) as yellow oil. MS (ESI, pos. ion) m/z 422,424[M+H]+. Step 2. (S)-cyclopropyl(5-(3,4-difluorophenoxy)-2-methyl-6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-3,4-dihydroquinolin-l(2H)-yl)methanone and (S)-cyclopropyl(5-(2,5- difluorophenoxy)-2-methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4- dihydroquinolin-l(2H)-yl)methanone [0666] A mixture of (S)-(6-bromo-5-(3,4-difluorophenoxy)-2-methyl-3,4-dihydroquinolin-l(2H)- yl)(cyclopropyl)methanone and (S)-(6-bromo-5-(2,5-difiuorophenoxy)-2-methyl-3,4- dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone (0.100 g, 0.24 mmol), bis(pinacolato)diboron (0.600 g, 2.37 mmol), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.019 g, 0.02 mmol), and potassium acetate (0.046 mg, 0.47 mmol) in 1,4-dioxane (10 mL) was stirred overnight at 80 C. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by p…

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; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7411-23-6, name is 3,5-Dibromo-1H-1,2,4-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. Product Details of 7411-23-6

In a 250 mL round bottomed flask sodium hydride (60% dispersion in mineral oil) (264 mg, 6.61 mmol) was added to a colorless solution of 3,5-Dibromo-lH-l,2,4-triazole (Int-1, 1 g, 4.41 mmol) in DMF (22 ml). The resulting suspension was stirred at room temp during 30 min and 1,1,1, 2,3,3, 3-heptadeuterio-2-iodopropane (936 mg, 5.29 mmol) was added and the reaction was stirred at 40C over night.The reaction mixture was poured into 50 mL H20 and extracted with EtOAc (3 x 50 mL). The organic layers were washed with sat NaCl (3 x 50 mL), dried over MgS04 and concentrated in vacuo. The title compound was isolated as a light yellow liquid (1.35 g, 111 % yield). MS (ES+) m/z: 276.9 [(M+H)+].

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (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. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Bromo-1-methyl-1H-1,2,3-triazole

The crude was dissolved in 10ml of tetrahydrofuran /1.5mlDMF added potassium carbonate (1.14g, 8.30mmol), methyl iodide (471mg, 3.32mmol), 20 ~ 30 for 48 hours, 20ml of water and 20ml of ethyl acetate, layered aqueous layer was adjusted with hydrochloric acid, pH = 1-5, and extracted with 20ml of ethyl acetate, 40 concentrated under reduced pressure to 3ml, was cooled to 0 crystallization, filtration, 40 dried in vacuo to give 1-methyl -1H-1, 2,3-triazole-4-carboxylate 587mg, 50% yield.

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; The Haiya Chemical Co., Ltd.; Jiang, Yueheng; Que, Limin; Xu, Jun; Qin, Dongguang; Cai, Tong; (17 pag.)CN105585534; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 956317-36-5, A common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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 the 50 L reaction flask A,10 kg of 5-methyl-2- (1,2,3-triazol-2-yl) benzoic acid,1.5 L dichloromethane,Ice bath to 0 ,Under nitrogen, 640 g of oxalyl chloride was added,100 g of DMF,The reaction was stirred at room temperature for 2 h.In another 100L reaction flask B,1.25 kg of compound 6 was added,1 kg of triethylamine,30 L of dichloromethane,Stir at room temperature for 2h and then cool the ice bath to 0 C,Dropping the mixture in the reaction flask A,Drop finished,Placed at 10 C,HPLC monitoring. After the reaction,The reaction solution was diluted with water,And then extracted with DCM,The DCM phase was dried over anhydrous sodium sulfate,And finally concentrated under reduced pressure at 45 C to obtain a crude product,The crude product was passed through a column of silica gel (60-120 mesh)The eluent was a 2% methanol / dichloromethane system,The compound 7 was concentrated in a brown oily liquid,Weight 1.98 kg, yield: 88%.

The synthetic route of 956317-36-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Meiyugao Pharmaceutical Co., Ltd.; Chen Zhiyong; Wang Chunyan; Wang Cong; (26 pag.)CN106866632; (2017); A;,
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. 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, A new synthetic method of this compound is introduced below., Safety of 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Add intermediate I48kg (235mol) in the reaction vessel, add dichloromethane 300ml, start stirring, add Intermediate II48kg (235mol); add alkali stirring and mixing, add condensing agent EDC.HCL45kg, when added, control the temperature at 25 The following, the reaction was incubated at 24 ~ 27 , TLC monitoring, TLC showed the reaction was completed, the intermediate was obtained after 87kg (223mol), the yield 94.9%.The difference between Example 3 and Example 1 is that a combination of a condensing agent and a condensing agent such as 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and tris (2 , 6-dimethoxyphenyl) bismuth, the weight percentage of tris (2,6-dimethoxyphenyl) bismuth in the condensing agent is 25%Insulation 18 ~ 22 reaction, TLC monitoring, post-processing intermediate 88kg (225.6mol),Yield 96%.

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; Anhui Baishansheng Pharmaceutical Co., Ltd.; Chang Song; Wang Zheming; Wei Yong; Mu Longzhi; Wu Zhangshuan; Fan Zheng; (8 pag.)CN107298678; (2017); A;,
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. 202931-88-2, name is 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H5N3O

Example 17a: (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanolTo a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (1.45 g, 3.37 mmol, Intermediate 10: 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 added drop wise. After 2 minutes, 1-methyl-1H-1,2,3-triazole-5-carbaldehyde (580 mg, 5.22 mmol, Intermediate 18) 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 x 40 ml.) and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (5% CH3CN-DCM increasing to 30% CH3CN +2% MeOH) afforded the title compound as an off white amorphous solid. 1H NMR (600 MHz, CDCl3) delta 8.15 (d, J = 1.9 Hz, IH), 7.82 (d, J = 8.6 Hz, 1H), 7.54 (dd, J= 8.6, 2.0 Hz, 1H). 7.49 (d, J = 8.2 Hz, 2H), 7.38 (d, J= 8.1 Hz, 2H), 7.27 (s, 1H), 6.14 (d, J= 4.6 Hz, 1H), 5.05 (s, 1H), 4.33 (s, 2H), 4.07 (s, 3H), 3.95 (s, 3H).MS (ESI): mass calcd. for C22H18ClF3N4O2, 462.5 , m/z found 463.1 [M+H]+. Example 17a was purified by chiral SFC (Chiracel AD-H column (50 x 250 mm, 5 micron), Mobile phase: 12% EtOH-hexane with 0.2% Et3N). The first eluting enantiomer was Example 17b. The second eluting enantiomer was Example 17c.

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 202931-88-2.

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.; WO2015/57206; (2015); A1;,
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