Day: April 23, 2021

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

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. 74733-90-7, name is 2-(4-Bromophenyl)-2H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., category: Triazoles

General procedure: To a 15 ml tube was added 1a (50 mg, 0.31mmol), 2a (118.5 mg, 0.37 mmol), [Cp*RhCl2]2 (9.70 mg 5 mol%), AgNTf2(12.2 mg 10 mol%) in DCE (3.0 mL), The tube was sealed and stirred at 100 C for 24 h. After completion, the reaction mixture was concentrated in vacuo and purified by silica gel column chromatography (80:1 DCM/MeOH) to provide the product 3aa 128.4 mg (pale brown oil) in 93% yield.

According to the analysis of related databases, 74733-90-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yu, Zhu-Jun; Zhang, Chen; Li, Jiang-Lian; Liu, Yan-Zhao; Yu, Xin-Ling; Guo, Li; Li, Guo-Bo; Wu, Yong; Tetrahedron Letters; vol. 59; 29; (2018); p. 2816 – 2819;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 118863-62-0, These common heterocyclic compound, 118863-62-0, name is 3-(4-Bromophenyl)-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 mixture of ethyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yi)-7-[4- (trifluoromethyl)phenyl]-2-naphthoate (50 mg, 0.106 mmol) from Example 3, Step 1, PdCl2CdPPf)-CH2Cl2 adduct (8.68 mg, 10.63 mumol), 3-(4-bromophenyl)-lH-l,2,4-triazole (35.7 mg, 0.159 mmol) under vacuum, was added DMF (2 mL) and 2 M potassium carbonate (0.159 ml, 0.319 mmol). The mixture was stirred under a nitrogen atmosphere at 90 0C for 3 h. The reaction was worked up by the addition of water, extracted with ethyl acetate, dried over Na2SO4, and evaporated. The residue was purified by Combiflash chromatography (0- 100%EtOAc/hexane) to afford the desired intermediate ester. The ester was dissolved in 2 mL of THF and ImL of MeOH and treated with 1 mL of 2 N KOH at rt for 3 h. The reaction was worked up by the addition of aqueous citric acid, extracted with ethyl acetate, dried over Na2SO4, and evaporated. The residue was purified by Combiflash chromatography (0-30% solvent A/DCM with solvent A being a mixture of concentrated ammonia and MeOH (1 :4)) to afford the desired 4-[4-(4H”-[l,2,4]triazol-3-yl)-phenyl]-7-(4-trifluoromethylphenyl)-2-naphthoic acid as a solid. MS: M+H(+ESI)= 460.0 and M-H(-ESI)= 458.0.

Statistics shows that 3-(4-Bromophenyl)-1H-[1,2,4]triazole is playing an increasingly important role. we look forward to future research findings about 118863-62-0.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/70873; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

Copper(II) acetate (approximately 18.42 g, 101.4 mmol), 3-bromo-1H-1,2,4-triazole (10 g, 67.59 mmol), and 4 A molecular sieves (250 mg/0.33 mmol) were combined in dichloromethane and treated with 3,4-difluorophenyl boronic acid (14.94 g, 94.63 mmol), and pyridine (approximately 10.69 g, 10.93 mL, 135.2 mmol). The mixture was stirred at room temperature under air for 3 days. The reaction was filtered and the solid was washed with additional dichloromethane (200 mL). The combined organic layers were concentrated with silica gel and dry-loaded to purify on silica gel to afford 3-bromo-1-(3,4-difluorophenyl)-1,2,4-triazole (10.5 g, 54percent). MR (400 MHz, DMSO-^e) delta 9.30 (s, 1H), 8.08 – 7.96 (m, 1H), 7.77 – 7.62 (m, 2H) ppm. ESI-MS m/z calc. 258.95566, found 260.32 (M+l)+; Retention time: 0.96 minutes.

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; VERTEX PHARMACEUTICALS INCORPORATED; BETHIEL, Randy Scott; CAO, Jingrong; COLLIER, Philip, N.; DAVIES, Robert J.; DOYLE, Elisabeth; FRANTZ, James Daniel; GOLDMAN, Brian Anthony; GREY, Ronald Lee; GRILLOT, Anne-laure; GU, Wenxin; KOLPAK, Adrianne Lynne; KRAUSS, Paul Eduardo; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MESSERSMITH, David; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; WANG, Jian; (491 pag.)WO2018/106646; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 7170-01-6, 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

(To a solution of 3-methyl-i H-1,2,4-triazole (45.6 mg, 0.548 mmol) in THF (2 mL) at 0C was added NaH (2i.94 mg,0.548 mmol) and the resulting mixture was stirred for 10 mi (S)-Isopropyl 2-(6- (bromomethyl)-4-(4,4-dimethylpiperidin- 1 -yl)-5 -(4-(4-fluorophenethoxy)phenyl)-2- methylpyridin-3-yl)-2-(tert-butoxy)acetate (75 mg, 0.110 mmol) in THF (0.5 mL) was then added and the mixture was stirred for i6 h. At this point LCMS indicatedcompletion of reaction. Mixture was then concentrated and treated with iON NaOH (0.110 mL, 1.097 mmol) in Ethanol (1 mL) at 80C for 4 h. Mixture was then cooled and purified by prep HPLC to afford three compounds: (S)-2-(tert-butoxy)-2-(4-(4,4- dimethylpiperidin- 1 -yl)-5 -(4-(4-fluorophenethoxy)phenyl)-2-methyl-6-((3 -methyl-i Hi,2,4-triazol-i-yl)methyl)pyridin-3-yl)acetic acid (8 mg, 0.0 12 mmol, 10.76 % yield). ?HNIVIR (500MHz, DMSO-d6) oe 8.02 (s, 1H), 7.39 (dd, J8.i, 5.9 Hz, 2H), 7.32 (d, J8.i Hz, 1H), 7.15 (t, J=8.8 Hz, 2H), 7.12 – 7.03 (m, 3H), 5.62 (br. s., 1H), 4.91 (d, J16.i Hz, 1H), 4.74 (d, J=15.8 Hz, 1H), 4.35 – 4.14 (m, 2H), 3.62 (br. s., 1H), 3.07 (t, J=6.6 Hz, 2H), 2.76 (br. s., 1H), 2.38 (s, 3H), 2.19 (br. s., 1H), 2.10 (s, 3H), 1.90 (br.s, 1H), 1.51 (br. s., 1H), 1.29 (br. s., 1H), 1.16 (d, J=i0.6 Hz, 1H), 1.09 (s, 9H), 1.02 (d, J12.5 Hz, 1H),0.85 (br. s., 3H), 0.62 (s, 3H). LCMS (M+H) = 644.2.(S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin- 1 -yl)-5 -(4-(4-fluorophenethoxy)-phenyl)-2-methyl-6-((5 -methyl-i H-i ,2,4-triazol- 1 -yl)methyl)pyridin-3 -yl)acetic acid (3.2 mg,4.72 tmol, 4.30 % yield): ?H NIVIR (500MHz, IVIETHANOL-d4) oe 7.84 (s, 1H), 7.36 (dd,J=8.4, 5.5 Hz, 2H), 7.27 (d, J=8.2 Hz, 1H), 7.09 – 7.01 (m, 3H), 7.01 – 6.91 (m, 2H), 6.02(s, 1H), 5.21 (d, J=14.7 Hz, 1H), 5.06 (d, J14.7 Hz, 1H), 4.27 (td, J=6.6, 2.9 Hz, 2H),3.12 (t, J=6.6 Hz, 2H), 2.58 (s, 3H), 2.26 (s, 3H), 1.33 (d, J=7.4 Hz, 3H), 1.22 (s, 9H),0.79 (br. s., 6H). 4 piperidine hydrogens are not resolved. LCMS (M+H) = 644.2.(S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin- l-yl)-5 -(4-(4-fluorophenethoxy)-phenyl)-2-methyl-6-((3 -methyl-4H- 1 ,2,4-triazol-4-yl)methyl)pyridin-3 -yl)acetic acid (2.1 mg,3.10 tmol, 2.82% yield): ?H NMR (500MHz, IVIETHANOL-d4) oe 7.74 (s, 1H), 7.36 (dd,J=8.4, 5.7 Hz, 2H), 7.20 – 7.14 (m, 1H), 7.10 – 6.99 (m, 5H), 6.01 (s, 1H), 5.09 (s, 2H),4.27 (td, J=6.6, 3.2 Hz, 2H), 3.15 -3.07 (m, 2H), 2.54 (s, 3H), 2.18 (s, 3H), 1.32 (t, J=7.2Hz, 3H), 1.21 (s, 9H), 0.78 (br. s., 6H). 4 piperidine hydrogens are not resolved. LCMS(M+H) = 644.2.

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

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; EASTMAN, Kyle J.; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PATEL, Manoj; SIVAPRAKASAM, Prasanna; TU, Yong; (275 pag.)WO2017/25915; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1455-77-2, 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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

A mixture containing Co(NO3)2¡¤6H2O (58.2mg, 0.2mmol), Hdatrz (19.8mg, 0.2mmol) and NH2-H2ip (36.2mg, 0.2mmol) was dissolved in mixed H2O?CH3OH (v:v=1:1, 10.0mL) solution, and the initial pH value of the reactant mixture was adjusted to 6 by triethylamine. The resulting mixture was then transferred into a Teflon-lined stainless steel vessel (23.0mL) and heated at 165¡ãC for 96h under autogenous pressure. After the mixture was cooled to room temperature at a rate of 2.9¡ãCh?1, red block-shaped crystals suitable for X-ray analysis were obtained directly, washed with water and dried in air (Yield: 50percent, based on NH2-H2ip). Anal. Calc. for C36H32Co4N14O17: C, 37.01; H, 2.76; N, 16.78. Found: C, 37.04; H, 2.65; N, 16.72percent. IR (KBr pellet, cm?1): 3409 (br), 3319 (w), 3167 (w), 1625 (s), 1588 (s), 1559 (s), 1481 (s), 1449 (s), 1386 (s), 1322 (w), 1011 (m), 985 (m), 952 (w), 797 (w), 778 (w), 724 (w), 666 (w).

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

Reference:
Article; Zhao, Hong; Li, Hong-Xue; Liu, Zhong-Yi; Yang, En-Cui; Zhao, Xiao-Jun; Polyhedron; vol. 101; (2015); p. 29 – 36;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics