Day: March 9, 2021

Synthetic Route of 23579-79-5, These common heterocyclic compound, 23579-79-5, name is 3,5-Dibromo-1-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.

LiHMDS (1 Min THF, 420 mL, 420 mmol) was added dropwise at 0 C to a cooled (ice bath) solution of 3-amino-4-fluorobenzotrifluoride (70 mL, 527.8 mmol) and 1H-1,2,4-Triazole, 3,5-dibromo-1-methyl-(46a, 50 g, 207.6 mmol) in anhydrous THF (500 mL). The reaction mixture was stirred at room temperature (rt) for 20 h. A saturated aqueous NH4Cl solution was added slowly. The reaction mixture was extracted with dichloromethane (DCM) and the organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The resulting slurry was triturated in heptane/DIPE and a solid was formed,filtered and dried under vacuum at 60 C, to provide 65 in 78% yield; mp 159.2 C. 1H NMR (600 MHz, CDCl3) delta ppm 3.77 (s, 3H), 6.37 (d, J = 3.9 Hz, 1H),7.20-7.24 (m, 1H), 7.27-7.29 (m, 1H), 8.34 (dd, J = 7.7, 2.2 Hz, 1H). MS (ESI) m/z 339 [M+H].+ Anal. (C10H7BrF4N4) C, H, N.

Statistics shows that 3,5-Dibromo-1-methyl-1H-1,2,4-triazole is playing an increasingly important role. we look forward to future research findings about 23579-79-5.

Reference:
Article; Velter, Adriana I.; Bischoff, Franois P.; Berthelot, Didier; De Cleyn, Michel; Oehlrich, Daniel; Jaroskova, Libuse; Macdonald, Gregor; Minne, Garrett; Pieters, Serge; Rombouts, Frederik; Van Brandt, Sven; Van Roosbroeck, Yves; Surkyn, Michel; Trabanco, Andrs A.; Tresadern, Gary; Wu, Tongfei; Borghys, Herman; Mercken, Marc; Masungi, Chantal; Gijsen, Harrie; Bioorganic and Medicinal Chemistry Letters; vol. 24; 24; (2014); p. 5805 – 5813;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-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. Application In Synthesis of 1,4-Dimethyl-1H-1,2,3-triazole

A vessel containing (S)-6-(5-bromo-1-(trans-4-hydroxycyclohexyl)-1H-benzo[d]imidazol-2-yl)- 1 -(3 ,4-difluorophenyl)piperidin-2-one (intermediate 17, 50 mg,0.10 mmol), 1,4-dimethyl-1H-1,2,3-triazole (15 mg, 0.15 mmol), potassium acetate (50mg, 0.51 mmol) and tert-amyl alcohol (0.75 mL) was evacuated then backfilled withnitrogen three times. cataCXium A Pd G3 (7 mg, 10 tmol) was added and the mixturewas heated to 100 C for 18 h. The mixture was diluted with water (8 mL) then extracted with dichloromethane (3 x 8 mL). The combined organic phases were concentrated under reduced pressure to give the crude product. The crude product was purified by chromatography on silica gel (4 g column, 50-100% MeAc/isohexane) to afford a pale brown gum. The gum was triturated in tert-butyl methyl ether to yield (S)1 -(3 ,4-difluorophenyl)-6-(5-( 1 ,4-dimethyl- 1H- 1,2,3 -triazol-5-yl)- 1 -(trans-4- hydroxycyclohexyl)-1H-benzo[d]imidazol-2-yl)piperidin-2-one (26 mg, 0.047 mmol, 48% yield) as atan solid. LCMS (method 1): Rt 1.50 mi m/z 521 (M+H)t 1HNIVIR(DMSO-d6) 7.91 – 7.77 (m, 2H), 7.44 – 7.36 (m, 1H), 7.36 – 7.29 (m, 1H), 7.23 (dd, J= 8.5, 1.7 Hz, 1H), 7.09 -7.00 (m, 1H), 5.79 (t, J = 4.6 Hz, 1H), 4.71 (d, J = 4.1 Hz,1H), 4.41 – 4.26 (m, 1H), 3.94 (s, 3H), 3.73 – 3.61 (m, 1H), 2.55 (dt, J = 9.8, 6.2 Hz,2H), 2.48 – 2.24 (m, 2H), 2.23 (s, 3H), 2.21 – 2.12 (m, 1H), 2.08 – 1.91 (m, 3H), 1.91 -1.70 (m, 3H), 1.50- 1.35 (m, 2H), 1.25- 1.15 (m, 1H).

The synthetic route of 60166-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELLCENTRIC LTD; PEGG, Neil Anthony; TADDEI, David Michel Adrien; SHANNON, Jonathan; PAOLETTA, Silvia; QIN, Ting; HARBOTTLE, Gareth; (95 pag.)WO2018/73587; (2018); 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Methyl-1H-1,2,4-triazole

CuI (1.71 g, 8.9 mmol) and N,N’-dimethylethylenediamine (1.91 ml, 17.92 mmol) were added to a mixture of 2-amino-5-iodopyridine (5.03 g, 22.4 mmol), 3 -methyl- IH- 1,2,4- triazole (2.42 g, 29.1 mmol) and Cs2CO3 (14.60 g, 44.81 mmol) in DMF (40 ml). The r.m. was heated at 110 0C for 7 h., the r.m. was cooled, EtOAc was added and the mixure was washed with H2O. The H2O layer was extracted 5 times with EtOAc. The combined organic layers were dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was purified by RP preparative HPLC [RP Shandon Hyperprep C18 BDS (8 mum, 250 g, LD. 5 cm); mobile phase: a gradient of (0.25 % NH4HCO3 solution in H2O)/MeOH/CH3CN]. The product fractions were collected and the solvent was evaporated. Yield: 1.5 g of intermediate 56 (38 %). –

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:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; TRESADERN, Gary, John; TRABANCO-SUAREZ, Andres, Avelino; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2010/70008; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, 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. 288-36-8 name is 1H-1,2,3-Triazole, 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.

Intermediate 1 : 5-Fluoro-2-[1 ,2,3]triazol-2-yl-benzoic acid.5-Fluoro-2-[1 ,2,3]triazol-2-yl-benzoic acid. To a solution of 5-fluoro-2- iodo-benzoic acid (3.86 g, 14.65 mmol), 2H-[1 ,2,3]triazole (2.5 g, 36.2 mmol), Cs2C03 (8.62 g, 24.5 mmol), frans-N,N’-dimethyl-cyclohexane-1 ,2-diamine (0.4 mL), Cul (244 mg) and DMF (13 mL) were added to a microwave ready vessel and heated to 100 C for 10 min. The mixture was cooled, diluted with water, and extracted with EtOAc. The aqueous layer was acidified and extracted with EtOAc. The organic layer was dried over Na2S04 and concentrated.Chromatography (DCM to 10% MeOH/1 % HOAc/DCM) gave the product as a white powder (2.14 g, 71 %). 1H NMR (400 MHz, CD3OD): 7.91 (s, 2H), 7.76 (dd, J = 8.9, 4.8 Hz, 1 H), 7.59 (dd, J = 8.5, 2.9 Hz, 1 H), 7.49 – 7.42 (m, 1 H).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4928-88-5,Some common heterocyclic compound, 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, molecular formula is C4H5N3O2, 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 3A Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate (20) A mixture of methyl 1,2,4-triazole-3-carboxylate (0.64 g, 5 mmol), 1,2,3,5-tetra-O-acetyl-beta-L-ribofuranose (2) (1.5 g, 4.72 mmol) and bis(p-nitrophenyl)-phosphate (20 mg) were placed in a pear shaped flask and placed in a preheated oil bath at (160-165¡ã C.). The flask was connected to a water aspirator and kept at 160-165¡ã C. (oil bath temperature) under reduced pressure with stirring for 25 min. The reaction mixture was removed, cooled and diluted with EtOAc (150 mL) and sat. NaHCO3 (100 mL). The product was extracted in EtOAc. The organic extract was washed with water (100 mL) and brine (50 mL), dried and evaporated to dryness. The residue that obtained was purified by flash column of silica gel using CHCl3 –>EtOAc as the eluent. The pure fractions were collected and evaporated to dryness to give 1.2 g (66percent) of pure product: 1 H NMR (CDCl3) delta 2.10 (3s, 9H, 3 COCH3), 3.98 (s, 3H, OCH3), 4.22 (m, 1H), 4.46 (m, 2H), 5.54 (t, 1H), 5.76 (m, 1H), 6.04 (d, 1H, C1′,), and 8.38 (s, 1H, C3 H). Anal. Calc. for C15 H19 N3 O9 (385.22): C, 46.75; H, 4.97; N,10.91. Found: C, 46.82; H, 4.57; N=10.71.

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

Reference:
Patent; ICN Pharmaceuticals, Inc.; US6130326; (2000); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-36-8, 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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows.

Example 120: Preparation of 4,5-dibromo-lH-?,2,31triazoleRr Br. BrN^ NH *” ‘ V NVNH To a solution of IH-[1, 2,3]triazole (1.26 ml, 21.7 mmol) in water (10 ml) at 5tfC, was added bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at 5CPC for 1.5 hours. The white solid (2.375 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (1.83 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (375 mg) was isolated via filtration and washed with water (5ml). The white solids were combined and dried to give 4,5-dibromo- IH-[1, 2,3]- triazole (4.92 g, 93% yield). M.p. 194.7C.

The chemical industry reduces the impact on the environment during synthesis 1H-1,2,3-Triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SYNGENTA LIMITED; WO2007/96576; (2007); 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. 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, A new synthetic method of this compound is introduced below., COA of Formula: C9H7N3O

Weigh 1.73 g (10 mmol) of 1,2,4-triazole benzaldehyde, 4.15 g (12 mmol) of fluorescein hydrazide, dissolved in50 mL of hot ethanol, and added to a 100 mL three-pack equipped with a thermometer and a stirring device. In the flask.To the above mixed solution,0.63 ml (10 mmol) of glacial acetic acidwasadded, and the mixture was refluxed under stirring at 80 C for 5 h, cooled to room temperature, and a white solid was precipitated,washed with cold ethanol, and dried under vacuum at 50 C for 8 h to obtain the final product compound. (Triazolyl benzaldehyde to fluorescein hydrazide Schiff base).Yield: 84%.

The synthetic route of 27996-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qilu University of Technology; Duan Hongdong; Zhong Wenxia; (12 pag.)CN109867683; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3641-08-5, name is 2H-1,2,4-Triazole-3-carboxamide, molecular formula is C3H4N4O, 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. category: Triazoles

EXAMPLE 4 Preparation of 1(and 2 and 4)-Benzoyl-s-triazole-3-carboxamide To a cooled, stirred mixture of 3 g. of 1,2,4-triazole-3-carboxamide and 4 g. of benzoyl chloride in 125 ml. of anhydrous diethyl ether is added rapidly 2.75 g. of triethylamine. The cooling bath is removed and the mixture is stirred at room temperature for 18 hours. The heterogeneous mixture is filtered and washed successively with diethyl ether, cold water and then diethyl ether and dried in vacuo for 4 hours yielding 4 g. of colorless solid. This solid is extracted with hot, dry acetonitrile and cooled yielding a solid product which is collected, washed with acetonitrile and dried in vacuo, yielding 1 g. of product, m.p. 174-178 C. (dec.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3641-08-5, its application will become more common.

Reference:
Patent; American Cyanamid Company; US4006159; (1977); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 6523-49-5, 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. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

Example B3; Preparation of (compound 3); Reaction under Argon flow. Dry DMSO (0.5 ml) was added to a mixture of intermediate 5 (0.000428 mol) and 4-(lH-l,2,4-triazol-l-yl)-benzenamine (0.000642 mol). The reaction mixture was stirred for 6 hours at 100 C on an oil-bath (no result; only starting material). Cs2CO3 (0.227 g, 1.5 equiv) was added and the reaction mixture was stirred for 3 hours at 100 0C. This mixture was extracted with a mixture of EtOAc/NaHCO3/H2O/NaCl. The extract’s solvent was evaporated. The residue (0.172 g) was washed with diethyl ether, a mixture of diethyl ether/DCM, then purified by EPO column chromatography over silica gel (eluent: toluene/2-propanone gradient). The product fractions were collected and the solvent was evaporated, yielding 0.024 g of compound 3, melting point 222.5-224 0C.

The chemical industry reduces the impact on the environment during synthesis 4-(1,2,4-Triazol-1-yl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/74984; (2006); 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. 815588-93-3, name is 1-Methyl-1H-1,2,4-triazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 815588-93-3

A mixture of 1 -methyl-1 H-1 , 2, 4-triazole-5-carboxylic acid (7.0 g, 55.1 mmol) in SOCI2 (20 mL) was heated to 70 ¡ãC for 2 h. The mixture was concentrated to dryness. The residue was dissolved in NHa/MeOH (7M, 40 mL) and stirred at rt overnight. The precipitated solid was filtered off, extracted with Et20 and dried under reduced pressure to give the title compound.

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 815588-93-3.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; DEUSCHLE, UIrich; STEENECK, Christoph; ALBERS, Michael; HOFFMANN, Thomas; (62 pag.)WO2018/153893; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics