Month: April 2021

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., Product Details of 135242-93-2

To a cooled (ice bath) solution of (1-methyl- 1H-1 ,2,4-triazol-3-yl)methanol (400 mg, 3.54 mmol) and DIEA (0.98 mL, 7.1 mmol) in CH2CI2 (35 mL) wasadded MsCI (0.41 mL, 5.3 mmol). The reaction was stirred at roomtemperature for 3 h then quenched with NaHCO3 (sat) (20 mL). The layers wereseparated and the aqueous layer was back-extracted with CH2CI2 (15 mL x 2).The combined organic layers were washed with brine (20 mL x 2) then dried over anhydrous Na2504, filtered and concentrated to give(1-methyl- 1H-1 ,2,4-triazol-3-yl)methyl methanesulfonate (650 mg, 96%) asyellow oil. 1H NMR (400 MHz, ODd3) O [ppm] 8.05 (s, 1H), 5.29(s, 2H), 3.93(s,3H), 3.09 (5, 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; PFIZER INC.; ITEOS THERAPEUTICS; NINKOVIC, Sacha; CROSIGNANI, Stefano; SCALES, Stephanie Anne; MCALPINE, Indrawan James; COLLINS, Michael Raymond; MADERNA, Andreas; WYTHES, Martin; (295 pag.)WO2016/147144; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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 16681-70-2, Recommanded Product: 16681-70-2

[0764] 3H-1,2,3-triazole-5-carboxylic acid (2.5 mg, 22f.tmol) was combined with HATU (8.4 mg, 22 flillOI) in DMF(0.3 mL) and stirred for 10 minutes; Et3N (1 eq.) was addedand the mixture was stirred for 1 minute. Compound 2 (22f.tmol) was dissolved in DMF (0.5 mL) and Et3N (3.1 f.LL, 22f.tmol) was added, followed by addition of the activated acidsolution. The mixture was stirred for 30 minutes, concentrated,and purified by preparative HPLC to yield Compounda (7 mg) as a TFA salt. MS m/z [M+Ht calc’d forC26H29CIFN50 4 , 530.19. found 530.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-[1,2,3]Triazole-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7170-01-6, name is 3-Methyl-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 7170-01-6, name: 3-Methyl-1H-1,2,4-triazole

A mixture of 20 (1.1 g, 3.5 mmol) and 3-methyl-1H-1,2,4-triazole (1.4 g, 17.5 mmol) was stirredat 170 C for 2 h. After cooled down to room temperature, the reaction mixture was diluted with H2O(30 mL) and extracted with DCM (30 mL ¡Á 2). The combined organic phases were washed with brine(30 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Theresidue was purified by column chromatography (silica gel, 0-100% EtOAc in petroleum ether) togive 21 (732 mg, 58.2% yield) as a yellow solid. LC-MS (ESI): m/z [M + 1]+ = 360.35

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyl-1H-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Article; Meuser, Megan E.; Rashad, Adel A.; Ozorowski, Gabriel; Dick, Alexej; Ward, Andrew B.; Cocklin, Simon; Molecules; vol. 24; 8; (2019);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1455-77-2, name is 3,5-Diamino-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 1455-77-2, HPLC of Formula: C2H5N5

A solution of 9.0 g 3,5-diamino-1,2,4-triazole and 22.4 ml diethyl phenylmalonate in N,N-dibutylbutan-1-amine is heated under microwave irradiation to 180¡ã C. for 8 h. The reaction mixture forms two layers after cooling to room temperature. The top layer is removed and the solvent of the lower layer is evaporated. The residue is treated with water and acidified with 5N HCl. The precipitated product is collected by filtration and dried. The crude product is used without further purification.MS (M+1): 244

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Holder, Swen; Vennemann, Matthias; Beneke, Gerrit; Zulch, Armin; Gekeler, Volker; Beckers, Thomas; Zimmermann, Astrid; Joshi, Hemant; US2009/137607; (2009); 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. 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

(R)-1-benzyl-5-methyl-1,4-diazepane (14.7 mmol)3.66 g of 5-methyl-2-(2 H-1,2,3-triazol-2-yl)benzoic acid18.03 mg)was dissolved in DMF and 2.43 g H0Bt (18.55 mmol), 6 mL TEA (42.75 mmol), 3.45 g EDC (17.99 mmo1) C, reaction 2h.A saturated solution of NaHCO3 and EA were added and the aqueous layer was washed three times with EA and the organic layers were combined.The organic layer was washed with citric acid solution, and the product was fully salified into aqueous phase. The aqueous phase was washed with EA after adding sodium carbonate to adjust pH> 9 and EA was washed three times. The combined organic layer was washed with saturated brine, dried with MgSO4, And EA (4: 1) (yield: 98.36%

According to the analysis of related databases, 956317-36-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WUHAN JIAYU TECHNOLOGY CO. LTD; ZHANG, GU ISEN; LIU, BIFENG; ZHOU, YAN; (18 pag.)CN103923068; (2016); B;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 6818-99-1, These common heterocyclic compound, 6818-99-1, name is 3-Chloro-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.

Under an atmosphere of argon, (2S,4R)-N-(1-cyanocyclopropyl)-4-(4-fluorophenylsulfonyl)- 1- (1- (trifluoromethyl)cyclopropanecarbonyl)pyffolidine-2-carboxamide (example 33, step b, 0.3 g, 634 imol) was combined with N,Ndimethylacetamide (12 mL) to give a colorless suspension. 3-Chloro-1H-1,2,4-triazole (134 mg, 1.27 mmol) and cesium carbonate (413 mg, 1.27 mmol, Eq: 2) were added. The reaction mixture was stirred over the weekend at ambient temperature, and wassubsequently heated to 140C for 30 mm in a microwave oven. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (2 x 50 mL). The crude material was purified by preparative HPLC to yield the title compound as a colorless viscous oil (93.9mg, 26.6 %). mlz = 557.09 [M+H?i.

The synthetic route of 6818-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAAP, Wolfgang; KUHN, Bernd; LUEBBERS, Thomas; PETERS, Jens-Uwe; (93 pag.)WO2017/144483; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, 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. HPLC of Formula: C9H7N3O2

A solution of (3S,6R)-6-methylpiperidin-3-ol (2.36 g, 20.5 mmol), 2-(2H- 1,2,3- triazol-2-yl)benzoic acid (4.65 g, 24.6 mmol), EDC (7.86 g, 41.0 mmol), l-hydroxy-7- azabenzotriazole (5.58 g, 41.0 mmol), and triethylamine (8.57 mL, 61.5 mmol) in DMF (130 mL) was stirred at 50 C overnight, then diluted with saturated aqueous sodium bicarbonate and extracted 5x with ethyl acetate. The organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel gradient chromatography (0-100% ethyl acetate in hexanes), providing the titled compound as a peach- colored solid. LRMS m/z (Mu+Eta) 287.4 found, 287.1 required.

The synthetic route of 1001401-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/95108; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 7411-23-6, These common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-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.

Triazole 1, 85.0 g (0.38 mol), was dissolved in 500 mL of ethyl acetate, 2-3 drops of trifluoroacetic acid were added, the mixture was heated to 50 C, and 75.0 g (0.87 mol) of 3,4-dihydro-2H-pyran was added over a period of 2.5 h. The mixture was refluxed for 1 h with stirring and evaporated, and the residue was recrystallized from toluene. Yield 111.5 g (95 %), mp 116-117 C [15]. IR spectrum, nu,cm-1: 2951, 2901, 2869, 2361, 1448, 1418, 1364, 1310,1289, 1240, 1204, 1184, 1082, 1055, 1042, 1001, 982,939, 912, 880, 847, 820, 793, 700, 563. 1H NMR spectrum,delta, ppm: 1.43-1.60 m (2H), 1.61-1.79 m (1H),1.84-2.04 m (2H), 2.04-2.20 m (1H), 3.54-3.76 m(1H), 3.91 d.d (1H, 3J = 3.2, 2J = 8.7 Hz), 5.54 d.d (1H, 3J = 2.5, 9.2 Hz). 13C NMR spectrum, deltaC, ppm: 21.7(CH2), 24.7 (CH2), 28.7 (CH2), 67.3 (CH2O), 84.6(OCH), 132.0 (C3), 140.0 (C5). Mass spectrum, m/z(Irel, %): 86 (5.8), 85 (100), 67 (10.8), 57 (11.1), 55 (8.4), 43 (8.9), 41 (18.9), 39 (6.5), 29 (17.8), 27 (8.7).

Statistics shows that 3,5-Dibromo-1H-1,2,4-triazole is playing an increasingly important role. we look forward to future research findings about 7411-23-6.

Reference:
Article; Tolstyakov; Russian Journal of Organic Chemistry; vol. 54; 10; (2018); p. 1537 – 1547; Zh. Org. Khim.; vol. 54; 10; (2018); p. 1525 – 1534,10;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route 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.

4′-methoxy 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-(4-methoxyphenyl)propenone (yield 99percent) 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 61percent).

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

Electric Literature of 41253-21-8,Some common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added 1,2,4-triazole sodium salt (6.3 g, 70 mmol) and the mixture stirred at 90 0C for 3 h after which the mixture was filtered and the solvent removed. The resulting residue was adsorbed onto silica gel and intermediates 67 and 68 separated by flash chromatography, eluting with 0% to 30% ethyl acetate/hexanes.Intermediate 674-Fluoro-2-(lH-l,2,4-triazol-l-yl)benzonitrile. Colorless needles (2.46 g,18% yield) 1H NMR (500 MHz, CDCl3) delta: 8.89 (IH, s), 8.19 (IH, s), 7.85 (IH, dd, J = 8.7, 5.6 Hz), 7.60 (IH, dd, J= 8.8, 2.4 Hz), 7.28-7.24 (IH, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13. Intermediate e 684-(lH-l,2,4-Triazol-l-yl)-2-fluorobenzonitrile. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) delta: 8.66 (IH, s), 8.15 (IH, s), 7.79 (IH, dd, J= 8.5, 6.7 Hz), 7.69 (IH, dd, J= 9.5, 1.8 Hz), 7.65-7.63 (IH, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Sodium 1,2,4-triazol-1-ide, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics