Month: May 2021

Synthetic Route of 4922-98-9, 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. 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of aminotriazole 11a?m (3.1mmol), glacial acetic acid (5mL), and diethyl ethoxymethylenemalonate (4.6mmol) was refluxed for 3h. After cooling to room temperature, the resulting precipitate was collected by filtration, washed with cold water and dried. The residue was stirred with cold ethyl ether (20mL) and filtered to afford the desired product. Following general procedure C, compound 12c was isolated as a white solid. Yield 67percent, mp>300°C. 1H NMR (200MHz, DMSO-d6) delta: 14.00 (br s, 1H); 8.64 (s, 1H); 8.14?8.10 (m, 2H); 7.55 (m, 3H); 4.26 (q, J=7.0Hz, 2H); 1.28 (t, J=6.8Hz, 3H)

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, 5-Phenyl-1H-1,2,4-triazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Aghazadeh Tabrizi, Mojgan; Baraldi, Pier Giovanni; Ruggiero, Emanuela; Saponaro, Giulia; Baraldi, Stefania; Poli, Giulio; Tuccinardi, Tiziano; Ravani, Annalisa; Vincenzi, Fabrizio; Borea, Pier Andrea; Varani, Katia; European Journal of Medicinal Chemistry; vol. 113; (2016); p. 11 – 27;,
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. 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. COA 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.

The synthetic route of 4922-98-9 has been constantly updated, and we look forward to future research findings.

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

Electric Literature of 423165-07-5,Some common heterocyclic compound, 423165-07-5, name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, molecular formula is C13H22N4, 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 an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C. N?-{2-Chlorophenyl)-[3-(3-isopropyl-5-methyl-[1,2,4]-triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]methyl}hydrazinecarboxamide (4a): White solid, yield: 75.85 %, m.p. 230-232 C. IR (KBr, numax, cm-1): 3464, 3242, 3151, 3060, 2987,1722, 1654, 1591, 1510, 1415, 1344, 1278, 1219, 1157, 1093,1051, 1033, 918, 852, 736, 627. 1H NMR (DMSO-d6, 400 MHz):delta10.49 (s, 2H, -NH2, D2O exchangeable), 8.26 (s, 1H, chiralproton), 8.15-8.18 (m, 1H, Ar-H, J1= 6.023 Hz, J2= 3.51 Hz),7.47-7.49 (m, 1H, Ar-H, J1= 5.27 Hz, J2= 3.26 Hz, J= 7.027Hz),7.368-7.397 (m, 2H, Ar-H, J2= 3.514Hz, J2= 6.023 Hz),6.589 (br, s, 2H, -2NH), 3.789 (s, 3H,-CH3), 3.46 (m, 1H, Ha),3.31-3.36 (1H, m, J= 9.53 Hz), 2.668-2.677 (m, 2H, J= 1.757Hz), 2.326-2.335 (m, 2H, J= 1.757 Hz), 1.88-1.97 (m, 4H, J1= 1.225 Hz, J2= 2.008 Hz), 1.253-1.236 (d, 6H, 2 × CH3, J=7.027 Hz); 13C NMR: 8.1 (CH3), 24.4 (2 × CH3), 28.4 (2 ×CH2), 26.3 (1CH)-isopropyl), 31.8 (1CH), 36.6 (2 × CH2), 52.7(2 × CH), 65.2 (1CH, adjacent to arom. ring), 126.3, 128.4,128.6, 130.4, 136.7, 137.3 (6C-arom. ring), 158.8 (-C=O,amide), 163.7 (2C, imine (C=N)). Mass: m/z: 429 (M-2), 391((M-2)-isopropyl), 414 ((M-2)-NH3), 301, 309, 279.

The synthetic route of 423165-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Viveka, T. Lakshmi; Sharada, L. Nalanda; Asian Journal of Chemistry; vol. 30; 9; (2018); p. 2029 – 2034;,
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. 40253-47-2, name is Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 40253-47-2

To a mixture of 285 ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate (200 mg, 1.29 mmol) in 166 THF (5 mL) was added 192 LiAlH4 (245 mg, 6.45 mmol) at 0 C. under N2. The mixture was stirred at 30 C. for 1 hour. The mixture was filtrated and washed with methanol, concentrated in vacuo to 286 give(5-methyl-1H-1,2,4-triazol-3-yl)methanol (350 mg).

The synthetic route of 40253-47-2 has been constantly updated, and we look forward to future research findings.

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; (154 pag.)US2019/194189; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 13423-60-4, 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. 13423-60-4, name is 1-Phenyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 19trans-diiodo(N-cyclohexylamine)(1-methyl-3-phenyl-1,2,4-triazol-5-ylidene)platinum(II)Step 1: 1-phenyl-4-methyl-1,2,4-triazolium iodideMethyl iodide (0.13 ml; 2 mmol) is added to a solution of 1-phenyl-1,2,4-triazole-which was obtained according to Antilla, J. C. et al., Journal of Organic Chemistry 2004, 69, 5578-5587-(0.15 g; 1 mmol) in 1 ml of acetonitrile. This mixture is heated at 80 C. for 16 hours, and is then evaporated to dryness. The residue obtained is recrystallized from a minimum amount of ethyl acetate, thus making it possible to obtain 0.12 g of the desired product (41%) whose characteristics are the following:1H NMR spectrum (500.19 MHz, CDCl3, 20 C.) delta [ppm]=4.34 (s, 3H), 7.54 (m, 3H), 7.96 (d, 2H), 9.09 (s, 1H), 11.60 (s, 1H).

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

Reference:
Patent; SANOFI-AVENTIS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; US2011/172199; (2011); 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. 1533519-85-5, name is Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, A new synthetic method of this compound is introduced below., name: Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate

The compound VI (R was methyl, 96.0 g, 282.9 mmol, 1.0 eq.) Was dissolved in 2 L of ethyl acetate and stirred at 30 to 40 C. The catalyst b5 (1.42 mmol, 0.5% eq.) Was added successively,N.(70.5 g, 396.1 mmol, 1.4 eq.) Was added and reacted for 4 hours. To the reaction solution was added 2 L of petroleum ether, stirred for 0.5 hour, filtered, and 2 L of saturated sodium carbonate solution was added to the filtrate. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a pale yellow compound of formula V (R, methyl, 107.6 g) in a yield of 91% and a purity of 92.9%

The synthetic route of 1533519-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Xin To Lead Pharmaceutical Co., Ltd.; Wang Hui; Zhen Zhibin; Zhang Xiang; (10 pag.)CN106916115; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 81606-79-3, name is 2-(1,2,4-Triazol-1-yl)acetonitrile, 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. Application In Synthesis of 2-(1,2,4-Triazol-1-yl)acetonitrile

To a solution of [1,2,4] Triazol-1-yl-acetonitrile (1.5 grams, 13.9 mmol) in ethanol were added sodium carbonate (4.4 grams, 41.7 mmol) and hydroxylamine hydrochloride (3.86 grams, 55.5 mmol). The mixture was heated to 80 0C for overnight. The reaction mixture was concentrated and extracted with ethyl acetate and purified by column to get the desired product (1.9 grams).Yield: 97%1H NMR (200 MHz, CDC13+DMSO): delta 9.34 (bs, IH), 8.51 (s, IH), 7.95 (s, IH), 5.58 (bs, 2H),4.74 (s, 2H).ES-MS (m/z): 142 (M++1)

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

Reference:
Patent; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES, INC.; WO2008/143649; (2008); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 7170-01-6, These common heterocyclic compound, 7170-01-6, name is 3-Methyl-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.

To a solution of 3-methyl-1 H-1 ,2,4-triazole (1 g) in MeCN (40mL) was added Cs2C03 (3.72g) followed by benzyl bromoacetate (1 .89mL) and the mixture was stirred for 1 h at RT. The reaction mixture was diluted with EA and washed with water (2x) and brine. The aq. layers were extracted with EA (2x) and the combined org. layers were dried over MgS04, filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 100g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8:2; gradient in %B: 85/15 for 12CV, 85/15 to 75/25 for 2CV, 75/25 for 3CV) to afford 2.3g as yellowish oil (52:48 mixture of regioisomers). The mixture of regioisomers was purified by preparative chiral HPLC (I). Second eluting fraction: (3-methyl-[1 ,2,4]triazol-1-yl)-acetic acid benzyl ester. LC-MS (A): tR = 0.67min; [M+H]+: 232.16. 1 H-NMR (CDCI3): 8.05 (s, 1 H); 7.40-7.30 (m, 5H); 5.23 (s, 0.95H, CH2); 4.93-4.88 (3s, 2H); 2.42 (s, 3H). Roesy signal seen between CH (triazole) at 8.05ppm and CH2 at 4.93-4.88ppm.

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

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; CAROFF, Eva; MEYER, Emmanuel; (32 pag.)WO2018/11265; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7343-33-1,Some common heterocyclic compound, 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, molecular formula is C2H2BrN3, 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.

2- [6-Chloro-3- (ethanesulfonyl) pyridin-2-yl] -3-methyl-6 – [(trifluoromethyl) sulfanyl]-3H-imidazo [4,5-b] pyridine 200 mg, 60percent sodium hydride (oily) 54 mg, and a mixture of 1 ml DMF, was added 3-bromo-1H-1,2,4-triazole 198mg under ice-cooling. After the mixture was stirred under ice-cooling for 2.5 hours, a saturated aqueous solution layer was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and saturated brine, and dried with anhydrous sodium sulfate. The resulting organic layer was dried under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 83mg of the present invention of compounds beta39 that described below.

The synthetic route of 7343-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; NAKAJIMA, YUJI; OKAWARA, YUICHI; (263 pag.)JP2016/102104; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-70-2, A common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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: To a stirred solution of 680 mg (1 .78 mmol) (3aR,4S,7R,7aS)-8-{[2-(trifluoro-methyl)phenyl]sulfonyl}octahydro-1H-4,7-epiminoisoindole hydrochloride (1 :1 ) (Intermediate 1) in 10 mL DMF were added 301 mg 1 H-1 ,2,3-triazole-4-carboxylic acid (2.66 mmol, 1 .5 eq), 590 mu 4-methylmorpholine (5.3 mmol, 3 eq) and 1 .01 g HATU (2.66 mmol, 1 .5 eq). After stirring for 16 h at RT, the solution was subjected to preparative HPLC to yield 473 mg (60 %) 1 H-1,2,3-triazol-5-yl[(3aR,4S,7R,7aS)-8-{[2-(trifluoromethyl)phenyl]sulfonyl}octahydro-2H-4,7-epiminoisoindol-2-yl]methanone. LC-MS (Method A1 ): Rt = 0.98 min; MS (ESIpos): m/z = 442 [M+H]+ 1 H NMR (400 MHz, DMSO-d6): delta [ppm] = 1 .40 – 1 .65 (m, 4 H) 2.80 – 3.01 (m, 2 H) 3.1 1 (dd, 1 H) 3.44 (dd, 1 H) 3.93 – 4.10 (m, 1 H) 4.23 (br s, 2 H) 4.39 (br s, 1 H) 7.83 – 7.96 (m, 2 H) 7.98 – 8.07 (m, 1 H) 8.23 – 8.29 (m, 1 H) 8.34 (br s, 1 H) 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 0.851 (1 .86), 1 .154 (4.18), 1 .171 (8.33), 1 .189 (4.15), 1 .232 (5.06), 1 .352 (1 .25), 1 .476 (3.05), 1 .498 (3.54), 1.545 (3.32), 1 .568 (2.64), 1.907 (4.52), 1 .987 (16.00), 2.006 (1.15), 2.332 (1 .00), 2.518 (4.20), 2.523 (3.25), 2.673 (1 .07), 2.686 (1 .44), 2.727 (2.10), 2.869 (1.54), 2.888 (4.37), 2.900 (1.51), 2.919 (1.42), 2.936 (1.81), 2.950 (1.59), 3.079 (1.93), 3.098 (1.95), 3.112 (2.32), 3.133 (1.78), 3.418 (1.78), 3.437 (1.88), 3.450 (2.13), 3.469 (1.64), 3.987 (3.57), 3.999 (1.42), 4.017 (5.50), 4.021 (3.40), 4.034 (3.49), 4.052 (1.15), 4.229 (4.91), 7.884 (3.44), 7.886 (3.44), 7.894 (3.96), 7.901 (8.45), 7.905 (3.69), 7.913 (4.08), 7.918 (4.32), 7.932 (1.44), 7.936 (1.00), 8.004 (4.86), 8.010 (4.74), 8.022 (2.59), 8.027 (3.37), 8.256 (4.32), 8.261 (3.10), 8.274 (4.15), 8.279 (3.47), 8.342 (1.47).

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SIEBENEICHER, Holger; STEUBER, Holger; TER LAAK, Antonius; NUBBEMEYER, Reinhard; ROTTMANN, Antje; IRLBACHER, Horst; BADER, Benjamin; PETERS, Michaele; WAGENFELD, Andrea; (110 pag.)WO2018/114677; (2018); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics