Triazoles

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. 184177-83-1, name is 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one

100 mL three-neck flask was added 2-[(1S,2S)-1-ethyl-2-benzyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (formula III) (6.08 g) and DMSO (30 mL) were dissolved with stirring. A 25% aqueous solution of sodium hydroxide (1.7 mL) was added and the mixture was stirred for 15 min. Add (5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl 4-methylbenzenesulfonate (formula IV) (6.12 g), the mixture is stirred at 40-50 C for 12-18 h. The reaction mixture was poured into water (60 mL) with vigorous stirring, stirring vigorously for 30 min, suction filtration, the filter cake was washed with water (30 mL), and dried under vacuum at 50 C to obtain 8.83 g of the compound of formula (V), yield 95.6 %.

The synthetic route of 184177-83-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kunming Jida Pharmaceutical Co., Ltd.; Yang Zhuqi; Zhang Poyong; Sun Xiaomei; Wang Lijiang; Zhang Yun; (13 pag.)CN108239077; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-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 7411-23-6, HPLC of Formula: C2HBr2N3

An argon gas atmosphere was prepared in a reaction vessel, then, a compound MC7-a (100 g), potassium carbonate (110 g) and N,N?-dimethylformamide (500 mL) were added, and the mixture was heated up to 90 C. Thereafter, to this was added an N,N?-dimethylformamide (100 mL) solution containing a compound MC7-b (109 g), and the mixture was stirred at 100 C. for 1 hour. Thereafter, the mixture was cooled down to room temperature, ion exchanged water and chloroform were added, and the organic layer was extracted. The resultant organic layer was washed with ion exchanged water, dried over anhydrous magnesium sulfate, then, filtered through a filter paved with silica gel, and the resultant filtrate was concentrated under reduced pressure, thereby obtaining an oil. The resultant oil was purified by silica gel column chromatography (a mixed solvent of heptane and ethyl acetate), then, dried under reduced pressure at 45 C., thereby obtaining a compound MC7-c (117 g, yield: 94%) as a colorless oil. The compound MC7-c showed a HPLC area percentage value of 99.5% or more. This operation was conducted repeatedly, thereby obtaining a necessary amount of the compound MC7-c. (0446) TLC/MS (DART, positive): m/z=281.9 [M+H]+ (0447) 1H-NMR (CD2Cl2, 300 MHz): delta (ppm)=3.94 (d, 2H), 2.32-2.23 (m, 1H), 0.95 (d, 6H).

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Reference:
Patent; Sumitomo Chemical Company, Limited; ABE, Taichi; ASADA, Kohei; OHUCHI, Kazuei; (80 pag.)US2017/166599; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 7411-23-6, 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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) or 3-chloro-1,2,4-triazole (300 mg, 2.9 mmol), o-quinone methide precursor 2 (2.9mmol), and K2CO3 (1.2 g, 8.7 mmol) were refluxed for 4 h in DMF (10mL). After completion of the reaction, the mixture was cooled, andpoured into H2O (30 mL). The precipitate formed was collected by filtration,washed with H2O, dried, and recrystallized.

The chemical industry reduces the impact on the environment during synthesis 3,5-Dibromo-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, A new synthetic method of this compound is introduced below., category: Triazoles

To a solution of (-)(5R-cis)-5-(2,4-difluorophenyl)-5- (iodomethyl)tetrahydiO-3-furanmethanol (7Og) in lambdazetaiV-dimethylformamide (700 ml), 1,2,4- sodium triazole (9Og) and l,3-dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (17.7 ml) were added at ambient temperature. The resulting mixture was heated to 100 C and stirred for 24 hours. After completion of reaction (monitored by TLC),the reaction mass was cooled and quenched with demineralized water. The product was extracted with dichloromethane (2x500ml). The organic layer was treated with 6N hydrochloric acid (400 ml). The layers were separated and pH of the aqueous layer is adjusted to 8-9 with aqueous sodium hydroxide (50% w/v). The product from aqueous layer was extracted with ethyl acetate (2x500ml) and subsequently organic layer was washed with brine and dried over sodium sulfate. The solvent was removed to obtain 42g of the title compound.

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; IND-SWIFT LABORATORIES LIMITED; WO2009/141837; (2009); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1186050-58-7, 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 1186050-58-7 as follows.

Step 2) Synthesis of 2-fluoro-6- (2H-1, 2, 3-triazol-2-yl) benzoyl chlorideTo a solution of 2-fluoro-6- (2H-1, 2, 3-triazol-2-yl) benzoic acid (1.026 g, 4.953 mmol) in anhydrous DCM (20 mL) were added slowly sulfoxide chloride (11 mL, 150 mmol) and pyridine (0.08 mL, 1 mmol) . The reaction was heated to reflux and stirred for 3 hours, and then cooled and the solvent was removed in vacuo to give a product, which was used directly in the next step.

According to the analysis of related databases, 1186050-58-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; ZHANG, Ji; (90 pag.)WO2017/88759; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1257633-67-2,Some common heterocyclic compound, 1257633-67-2, name is 1-(tert-Butyl)-4-(diethoxymethyl)-1H-1,2,3-triazole, molecular formula is C11H21N3O2, 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 50-mL round bottom flask was added a solution of 1-tert-butyl-4-(diethoxymethyl)-1H-1,2,3-triazole (1.28 g, 5.63 mmol) in dichloromethane (6.0 mL), followed by addition of water (3.0 mL) and trifluoroacetic acid (1.0 mL) The reaction mixture was stirred vigorously under nitrogen for 3 h and then was diluted with EtOAc (100 mL), washed with sat aq NaHCO3 (3¡Á40 mL) and brine (40 mL). The combined organic phases were dried over anhydrous MgSO4, filtered. Solvent was removed and the residue was used in the next step without purification. 1H NMR complies with the reported value.

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

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCACATION; Zeng, Dexing; (26 pag.)US2017/297008; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. category: Triazoles

R-7 (300 mg, 0.77 mmol) in DMSO (5 ml) is treated with 3-methyl-lH-(l,2,4)-triazole (77 mg, 0.93 mmol) and potassium carbonate (210 mg, 1.55 mmol). The resulting mixture is warmed to 75 C for 2 hours and cooled to ambient temperature. The reaction is poured into water and the product is extracted into ethyl acetate. The combined organics are dried with MgS04, filtered and concentrated. The residue is sequentially purified by silica gel flash column chromatography with 0-10% MeOH in CH2CI2 as the eluent and reverse phase HPLC with 22% acetonitrile (0.1% TFA) in water (0.1% TFA) to give 2 (90 mg).

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DE LOMBAERT, Stephane; LIU, Weimin; LO, Ho Yin; NEMOTO, Peter Allen; WO2012/61169; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 135242-93-2,Some common heterocyclic compound, 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, molecular formula is C4H7N3O, 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.

a 1-Methyl-1,2,4-triazole-3-methylamine hydrochloride 1-Methyl-1,2,4-triazole-3-methanol (500 mg, 4.4 mmol) was added to ice-cold thionyl chloride (5 ml, 69 mmol). The mixture was heated at reflux for 0.75 h, then cooled to room temperature and evaporated in vacuo. The residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution and the aqueous layer separated and further extracted with dichloromethane (*2). The combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was treated with 33% w/w aqueous ammonia (5 ml) and the mixture heated in a sealed tube at 80 C. for 16 h. After cooling to room temperature, the reaction mixture was evaporated in vacuo and azeotroped with ethanol to give the title-amine (600 mg, 92%), 1H NMR (250 MHz, d6-DMSO) delta 3.88 (3H, s, Me), 4.04 (2H, s, CH2), 8.36 (2H, br s, NH2), 8.58 (1H, s, Ar-H).

The synthetic route of 135242-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Limited; US6200975; (2001); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 252742-72-6, 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. 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 108; 5-({[(4-bromophenyl)methyl]thio}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one; [Show Image] To a solution of 5-(chloromethyl) -2,4-dihydro-3H-1,2,4-triazol-3-one obtained according to the methods described in Tetrahedron Letter, 2000, 41, 8661 and the like (2.00 g, 15.0 mmol), (4-bromophenyl)methanethiol (3.04 g, 15.0 mmol) and potassium carbonate (2.48 g, 0.369 mmol) in THF (4 mL) was added a suspension of O-(trimethylsilyl)hydroxylamine (0.271 mL, 18.0 mmol) in DMF (40 mL) at room temperature, and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. The solid was washed with water and diethyl ether to give the title compound as a white powder (3.97 g, 88percent). 1H-NMR (300MHz, DMSO-d6) delta: 3.36 (2H, s), 3.70 (2H, s), 7.28 (2H, d, J = 8.3 Hz), 7.52 (2H, d, J = 8.3 Hz), 11.29 (1H, br), 11.39 (1H, br).

The chemical industry reduces the impact on the environment during synthesis 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1953148; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. Quality Control of Sodium 1,2,4-triazol-1-ide

EXAMPLE 3; Preparation of crude Anustrozole:Tupsilon the title compound of example 2 (50g) in dry DMF (250ml), anhydrous potassium carbonate (26g) and triazole sodium salt (232 g) are added and the mixture stirred at room 25 temperature for 45 min. Worked up the reaction mixture by adding water ( 1500 ml) and extraction with toluene (3 x 300ml). Combined toluene layer is washed with water (1 x300ml), washed toluene layer is dried over anhydous sodium sulphate, fitered and evaporated toluene to obtain crude anastrozole (4Og) having isomeric impurity 0.5%. EXAMPLE 4Preparation of crude Anastrozole:To the title compound of example 2 (500g) in dry DMF (250ml), anhydrous potassium carbonate (26Og) and triazole sodium salt (2320 g) are added and the mixture stirred at room iemperature for 45 min. Worked up the reaction mixture by adding water ( 15000 ml) and extraction with toluene (3 x 3000ml). Combined toluene layer is washed with water ( 1 3000ml), washed toluene layer is dried over anhydrous sodium sulphate, filtered and evaporated toluene to obtain crude anastrozole (45Og) having isomeric impurity 0.5%. EXAMPLE 5 Preparation of crude Anastrozole:To the title compound of example 2 (5Og) in dry DMF (250ml) anhydrous potassium carbonate (26g) and triazole sodium salt (232 g) are added and the mixture stirred at room temperature for 45 min. Worked up the reaction mixture by adding water (750 ml) and extracting with toluene (3 x 300ml). Combined toluene layer is washed with water ( 1 x300ml).The washed toluene layer is dried over anhydrous sodium sulphate, filtered and evaporated toluene to obtain crude anastrozole (42g) having isomeric impurity 4.52%.EXAMPLE 6Preparation of crude Anastrozole: To the title compound of example 2 (5Og) in dry DMF (250ml) anhydrous potassium carbonate (26g) and triazole sodium salt (232 g) are added and the mixture stirred at room temperature for 45 min. Worked up the reaction mixture by adding water (950 ml) and extracting with toluene (3 x 300ml). Combined toluene layer is washed with water ( 1 x30ml).The washed toluene layer is dried over anhydrous sodium sulphate, filtered and evaporated toluene to obtaincrude anastrozole (42g) having isomeric impurity 2.6%.EXAMPLE7Preparation of crude Anastrozole:To the title compound of example 2 (5Og) in dry DMF (250ml) anhydrous potassium carbonate (26g) and triazole sodium salt (232 g) are added and the mixture stirred at room temperature for 45 min. Worked up the reaction mixture by adding water (2500 ml) and extracting with toluene (3 x 300ml). Combined toluene layer is washed with water ( 1 .300ml).The washed toluene layer is dried over anhydrous sodium sulphate, filtered and evaporated toluene to obtain crude anastrozole (42g) having isomeric impurity 3.2%.

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; SHILPA MEDICARE LTD.; WO2007/105231; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics