Day: May 21, 2021

Adding a certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, 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 16681-65-5, HPLC of Formula: C3H5N3

To a flask containing 1-methyl-1H-1,2,3-triazole (100 mg, 1.2 mmol) was added THF (10 mL) and the colorless solution was cooled to -43 C. using a CH3CN-CO2 bath. Then, n-BuLi (2.5 M in hexanes, 490 muL, 1.23 mmol) was added dropwise which afforded an opaque mixture. The mixture was stirred at -40 C. for 30 minutes, then a homogeneous solution of (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone (255 mg, 0.54 mmol, Intermediate 80: step b) in 2 mL THF was introduced. After 5 minutes, the reaction mixture was then placed in an ice-water bath. The reaction was quenched after 20 minutes with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc (3*30 mL) and EtOAc:THF (1:1, 30 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The solid was triturated with MeOH and filtered to give a yellow filtrate which was concentrated and chromatographed on silica gel (3% MeOH-DCM increasing to 10% MeOH) to afford the title compound. 1H NMR (500 MHz, CDCl3) delta 8.22 (d, J=2.1 Hz, 1H), 7.76 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.1 Hz, 2H), 7.41-7.35 (m, 3H), 7.10 (s, 1H), 6.99 (s, 1H), 6.22 (s, 1H), 4.29 (s, 2H), 4.07 (s, 3H), 3.89 (s, 3H), 3.41 (s, 3H). MS (ESI): mass calcd. for Chemical Formula: C26H22ClF3N6O2; Exact Mass: 542.14. m/z found 542.9 [M+H]+. (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)(1-methyl-1H-imidazol-5-yl)methanol was purified by chiral SFC (Stationary phase: CHIRALPAK AD-H 5 mum, 250*20 mm, Mobile phase: 80% CO2, 20% mixture of MeOH/iPrOH, 50/50 v/v (+0.3% iPrNH2)), to give Example 89b as the first compound eluted from the chiral column and Example 89c as the second compound eluted from the chiral column.

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

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

Some common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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. HPLC of Formula: C3H3N3O2

1,2,3-Triazole-4-carboxylic acid (14 mg, 124 mumol), DIPEA (86.3 muL, 496 mumol) and HATU (47.1 mg, 124 mumol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid dimethylcarbamoylmethyl ester (49 mg, 120 mumol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product purified by preparative HPLC and lyophilized to yield the title compound (51 mg; purity 95%). MS m/z [M+H]+ calc’d for C26H31N5O5, 494.23. found 494.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-70-2, its application will become more common.

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); 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. 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, A new synthetic method of this compound is introduced below., Application In Synthesis of (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol

To a mixture of (1-methyl-1H-1,2,4-triazol-3-yl)methanol (400 mg, 3.54 mmol) and iodobenzene diacetate (1.25 g, 3.89 mmol) in dichloromethane (10 mL) was added TEMPO ((2,2,6,6-tetramethylpiperidin-1-yl)oxyl) (56 mg, 354 mumop. The mixture was stirred at 15-20 C. for 2 h. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=1:2) to give 1-methyl-1H-1,2,4-triazole-3-carbaldehyde (300 mg, 2.70 mmol, 76% yield). 1H NMR (chloroform-d 400 MHz) delta 10.01 (s, 1H), 8.19 (s, 1H), 4.06 (s, 3H).

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; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Kehler, Jan; Rasmussen, Lars Kyhn; Clementson, Carl Martin Sebastian; Marigo, Mauro; US2019/185489; (2019); 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H5N3

Example 123: tert-butyl-3-((4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(hydroxy)(1-methyl-1H-1,2,3-triazol-5-yl)methyl)azetidine-1-carboxylate To a flask containing 1 -methyl- 1 H- 1 ,2,3-triazole (430 mg, 0,8 mmol) was added THF (15 mL) and the solution was cooled to -43 C using a CH3CN-C02bath. Then, -BuLi, (2.5 M in hexanes, 0.7 mL, 1.75 mmol) was added dropwise. The reaction mixture was stirred at -40 C for 30 minutes, then tert-butyl-3-(4-chloro-2-methoxy-3-(4-(trifluoromethyr)benzyl)quinoline-6- carbonylj-azetidine- 1 -carboxylate (430 mg, 0.8 mmol, intermediate 61 : step b) in 2 mL THF was introduced. The reaction mixture was allowed to warm to room temperature over 30 minutes, and was quenched after 45 minutes with aqueous NH4C1 solution. The aqueous portion was extracted with EtOAc (3 x 30 mL). The combined organics were washed with brine, dried over MgS04, filtered and concentrated. Chromatography on Silica gel (10% acetone-hexane increasing to 30% acetone) afforded the title compound as a white amorphous solid. H NMR (500 MHz, CDCI3) 5 8.24 (d, J = 2.1 Hz, 1H), 7.78 (d, J= 8.8 Hz, IH), 7.56 – 7.47 (m, 3H), 7.40 (d. J ——- 8.1 Hz, 2H), 7.35 (dd, J = 8.7, 2.1 Hz, }. 4.35 (s, 2H), 4.20 (t, J = 8.8 Hz, IH), 4.07 (s,3H), 4.00 (dd, J = 9.3, 5.6 Hz, IH), 3.92 (dd, J = 8.9, 5.7 Hz, IH), 3.67 (s, 3H), 3.62 (t, J = 8.8 Hz, I H), 3.52 – 3.38 (m, IH), 1.38 (s, 9H); MS (ESI): mass calcd: Chemical Formula: C3oH3]ClF3504; Exact Mass: 617.2, m/z found 617.8 | M I I | .

According to the analysis of related databases, 16681-65-5, the application of this compound in the production field has become more and more popular.

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

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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1455-77-2

Acetophenone was used in place of 2-acetylthiophene in Reference Example 001 and heated to reflux in xylene in the presence of N,N-dimethylformamide diethyl acetal as in Reference Example 001, and 3-dimethylamino-1-phenylpropenone (yield 41percent) was obtained, which was subsequently reacted with 3,5-diamino-1,2,4-triazole in toluene in the presence of 10-camphor sulfonic acid and the title compound was obtained (yield 63percent).

The synthetic route of 1455-77-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIPPON KAYAKU KABUSHIKI KAISHA; EP1674454; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, molecular formula is C8H8N4, 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. HPLC of Formula: C8H8N4

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 150°C 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4922-98-9, its application will become more common.

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 27996-86-7, A common heterocyclic compound, 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, molecular formula is C9H7N3O, 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.

To a stirred solution of 4-(1 H-1 ,2,4-triazol-1-yl)benzaldehyde (400 mg, 2.28 mmol) in dry MeOH (5 ml_), NaBH4 (93 mg, 2.74 mmol) was added at 0 C and the resulting mixture was stirred at RT for 2 h. After completion of the reaction, ice water was added and the mixture was extracted with EtOAc (2 x 20 ml_). The combined organic layer was washed with brine (2 ml_), dried over Na2S04 and concentrated under vacuum. The resulting crude product was purified by flash chromatography (Eluent: 34% EA in pet ether) to get the title product. Yield: 67% (271 mg, white solid). 1H NMR (400 MHz, DMSO-cfe): d 9.27 (s, 1 H), 9.25 (s, 1 H), 7.78 (d, J = 8.6 Hz, 2H), 7.13 (d, J = 8.6 Hz, 2H), 4.85 (s, 1 H), 3.96 (s, 2H). LCMS: (Method A) 176.1 (M+H), Rt.1.04 min, 99.79% (Max).

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; ASCENEURON S. A.; QUATTROPANI, Anna; WISHART, Grant; KULKARNI, Santosh S.; RAKESH, Paul; (338 pag.)WO2020/39027; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 13423-60-4, The chemical industry reduces the impact on the environment during synthesis 13423-60-4, name is 1-Phenyl-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life.

General procedure: To a stirred, cooled (0 C) solution of 2,2,6,6-tetramethylpiperidine(0.50 mL, 3.0 mmol) in THF (5 mL) was added BuLi(about 1.6 M hexanes solution, 3.0 mmol). After 15 min at 0 C,ZnCl2TMEDA (0.25 g, 1.0 mmol) was added, and the mixture wasstirred for 15 min at this temperature before introduction of thesubstrate (2.0 mmol). After 2 h at room temperature, a solutionof I2 (0.74 g, 3.0 mmol) in THF (5 mL) was added. The mixturewas stirred overnight before addition of an aqueous saturated solutionof Na2S2O3 (10 mL) and extraction with CH2Cl2 (3 20 mL).The combined organic layers were dried over Na2SO4 and concentratedunder reduced pressure before purification by flash chromatographyon silica gel. 4.4.1 5-Iodo-1-phenyl-1H-1,2,4-triazole (6a) Compound 6a was prepared from 1-phenyl-1H-1,2,4-triazole (2a) using the general procedure 2 and was isolated (eluent: heptane/AcOEt 4:1) in 51% yield as a white powder: mp 109 C; IR (ATR): 3066, 2244, 1598, 1499, 1475, 1364, 1323, 1273, 1165, 994, 908, 761, 730, 693, 666 cm-1; 1H NMR (CDCl3, 300 MHz) 7.54 (br s, 5H), 8.10 (s, 1H); 13C NMR (CDCl3, 75 MHz) 99.8 (C), 126.1 (2CH), 129.4 (2CH), 129.8 (CH), 137.5 (C), 155.0 (CH). HRMS (ASAP): calcd for C8H7IN3 [M+H]+ 271.9685, found 271.9684. Crystal data for 6a (CCDC 1058467). C8H6IN3, M = 271.06, monoclinic, P21/c, a = 6.7529(2), b = 7.2343(2), c = 18.0011(6) A, beta = 95.0770(10), V = 875.95(5) A3, Z = 4, d = 2.055 g cm-3, mu = 3.600 mm-1. A final refinement on F2 with 2000 unique intensities and 109 parameters converged at omegaR(F2) = 0.0636 (R(F) = 0.0252) for 1886 observed reflections with I > 2sigma(I).

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-Phenyl-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nagaradja, Elisabeth; Bentabed-Ababsa, Ghenia; Scalabrini, Mathieu; Chevallier, Floris; Philippot, Stephanie; Fontanay, Stephane; Duval, Raphael E.; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Roisnel, Thierry; Mongin, Florence; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6355 – 6363;,
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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1H-1,2,3-Triazole

A solution of 2-iodobenzoic acid (3.0 g, 12.09 mmol) in DMF was treated with (1.5 g, 21.7 mmol) 1,2,3-triazole, 7.08 g (21.7 mmol) CsCO3, 114 mg (0.60 mmol) CuI and 310 mg (2.17 mmol) trans-N,N’-dimethylcyclohexane-1,2-diamine. The mixture was heated at 120 C. for 10 min in a microwave reactor. The reaction was cooled to rt, diluted with EtOAc, and filtered through Celite. The residue was purified by gradient elution on SiO2 (MeOH in DCM with 0.1% AcOH) to give the faster eluting desired 2-(2H-1,2,3-triazol-2-yl)benzoyl acid, A-1. Data for A-1: 1HNMR (500 MHz, DMSO-d6) delta 13.05 (br s, 1H), 8.12 (s, 2H), 7.81-7.52 (m, 4H) ppm. The undesired 2-(1H-1,2,3-triazol-2-yl)benzoic acid eluted second.

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bergman, Jeffrey M.; Breslin, Michael J.; Coleman, Paul J.; Cox, Christopher D.; Mercer, Swati P.; Roecker, Anthony J.; US2008/132490; (2008); 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. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-(1,2,4-Triazol-1-yl)aniline

A stirred solution of N’-(4-bromo-2-cyano-phenyl)-N,N-dimethyl-formamidine (0.5g, 2mmol, leq) and 4-[l,2,4]triazol-l-yl-phenylamine (0.32g, 2mmol, leq) in acetic acid (4mL) was heated to reflux for 2 hours then allowed to cool. After cooling, addition of diethylether afforded a yellow precipitate. The precipitate was collected by filtration, washed with diethylether then dried in vacuo to afford the desired compound as the acetate salt. (0.53g, 62%). 1H-NMR (DMSO-^6) delta 1.88 (s, 3H), 7.77 (d, IH), 7.90 (d, 2H), 8.02 (dd, IH), 8.08 (d, 2H), 8.25 (s, IH), 8.68 (s, IH), 8.90 (d, IH), 9.29 (dd, IH), 10.04 (s, IH). LC-MS rt 2.30 m/z 368 ES+.

The synthetic route of 6523-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics