Day: December 11, 2020

13273-53-5, 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. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

In a microwave tube to a mixture of 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indolin-2-one (100 mg, 395 imol, Eq: 1.00, cf. Example 70 step c) and 4-bromo-1-methyl-1H-1,2,3-triazole (76.7 mg, 474 imol, Eq: 1.2) was added acetonitrile (3 ml). The solvent was degassed by bubbling nitrogen through the suspension for 10 minutes. Then was added at 22 C N,N?5 dimethylethylenediamine (6.96 mg, 8.5 jil, 79.0 imol, Eq: 0.2) followed by potassium carbonate(136 mg, 987 imol, Eq: 2.5) and copper (I) iodide (7.52 mg, 39.5 imol, Eq: 0.1). The tube was inerted, sealed and the mixture was heated in microwave at 170C for 30 minutes.The mixture was treated with 2 ml of water and extracted with ethyl acetate (2 x 2 ml). The organic layers were dried, filtered and concentrated in vacuo.The residue was purified by chromatography on silica gel to give the desired compound as a white solid (8 mg, 6%). MS (mlz) = 335.2 [M + H].

The synthetic route of 4-Bromo-1-methyl-1H-1,2,3-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, 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 4922-98-9. 4922-98-9

Example 11; Part A; A reaction mixture of 3-phenyl-1 H-1 ,2,4-tpiazol-5-amiotane (160 mg, 1 mmol) and dimethyl but-2-ynediotaoate (123 mul_, 1 mmol) in methanol (2 ml_) was stirred at room temperature for overnight Purification using reverse phase HPLC gave compound 11-1 as a solid after lyophilization HPLC-MS RT= 3 08 mm, mass calculated for formula Ci3H10N4O3270 08, observed LCMS m/z 271 28 (M+H)

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 5-Phenyl-1H-1,2,4-triazol-3-amine.

Reference:
Patent; SCHERING CORPORATION; SHIPPS, JR., Gerald, W.; CHENG, Cliff, C.; HUANG, Xiaohua; ACHAB, Abdelghani, Abe; ORTH, Peter; VOIGT, Johannes, H.; SOUCY, Kyle, Ann; WO2010/56631; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 64922-04-9, name is Ethyl 1H-1,2,4-triazole-5-carboxylate, molecular formula is C5H7N3O2, 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. 64922-04-9

Example 1.10: Preparation of l-ethyl-lH-[l,2,,4~|triazole~3-carboxyric acid methyl ester and 1 -ethyl- IH-[1, 2,4]triazole-5-carboxylic acid methyl esterTo a suspension of IH-[1, 2,4]-triazole-3-carboxylic acid methyl ester (25 g, commercially available) in dry lambdazetaN-dimethylformamide (200 ml) at O0C under an atmosphere of nitrogen was added in portions sodium hydride (60% by weight dispersion in mineral oil) (8.66 g). On complete addition, the mixture was stirred for 1 hour at ambient temperature then re-cooled to O0C and ethyl iodide (15.5 ml) was added. The reaction mixture was stirred for 1 hour, stored for 18 hours then treated with aqueous ammonium chloride (IM) and concentrated to give a yellow oil. The oil was dissolved in chloroform (300 ml), washed with water (100 ml), dried over magnesium sulfate and concentrated. The oil that remained was washed with hexane and then triturated with diethyl ether to give a mixture of l-ethyl-lH-[l,2,4]triazole-3-carboxylic acid methyl ester and 1 -ethyl- IH-[1, 2,4]triazole-5-carboxylic acid methyl ester which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64922-04-9, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WO2008/74991; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

23579-79-5, A common compound: 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A mixture of 17.5 g (0.073 mol) of triazole 2a and 36.5 mL (0.73 mol) of 98 % hydrazine hydrate in 150 mL of propan-2-ol was refluxed for 5.5 h with stirring. The mixture was cooled, the precipitate was filtered off, and the filtrate was evaporated to a volume of 15 mL to isolate an additional amount of the product which was combined with the main portion and recrystallized from toluene. Yield 11.6 g (83 %), mp 196-197 C. IR spectrum, nu, cm-1: 3325 (NH), 3256, 2924,1634 (NH), 1582, 1521, 1456, 1437, 1429, 1331, 1294, 1246, 1227, 1132, 1024, 999, 947, 866, 731, 681, 608, 567, 557. 1H NMR spectrum, delta, ppm: 3.51 s (3H,CH3), 4.52 br.s (2H, NH2, overlapped by the signal of water present in the solvent), 7.84 s (1H, NH). 13C NMR spectrum, deltaC, ppm: 34.3 (CH3), 135.5 (C3),159.5 (C5). Mass spectrum, m/z (Irel, %): 193 (61.3) [M]+, 191 (64.2) [M]+, 178 (4.8), 177 (8.2), 176 (8.2), 175 (10.0), 174 (2.9), 164 (3.1), 163 (4.1), 161 (9.1), 159 (8.2), 136 (5.3), 135 (9.4), 134 (6.3), 133 (11.4), 112 (70.4), 108 (16.0), 106 (16.1), 95 (13.0), 83 (43.0), 82 (47.8), 81 (8.6), 80 (5.7), 78 (6.9), 68 (5.9), 56 (7.6), 55 (18.1), 53 (30.6), 43 (100), 42 (32.7), 41 (7.9), 40 (7.3), 31 (18.6), 30 (37.6), 29 (18.8), 28 (11.8), 27 (7.5), 17 (5.7), 16 (8.9), 15 (39.4). Found,%: C 19.07; H 3.11; N 36.87. C3H6BrN5. Calculated, %: C 18.77; H 3.15; N 36.47. M 192.02.

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, 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

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

15988-11-1,Some common heterocyclic compound, 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, molecular formula is C8H7N3O2, 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: Dimedone (0.14 g, 1 mmol), benzaldehyde (0.1 g, 1 mmol), and 4-phenylurazole (0.177 g, 1 mmol) were mixed with PEG-SO3H (0.6 g, 0.1 mmol) and the obtained mixture was stirred magnetically at 80 C for 40 min. After the completion of the reaction warm water (20 mL) was added and the mixture stirred for about 5 min. The insoluble crude product was filtered and recrystallized from EtOH/H2O 4:1 and the pure product was obtained (0.352 g, 91%). In order to recover the catalyst, the filtrate was dried under reduced pressure and recovered catalyst was washed with diethyl ether and reused after drying under reduced pressure. The equivalent procedure was used for the synthesis of triazolo[1,2-a]indazole-tetraones.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15988-11-1, its application will become more common.

Reference:
Article; Hasaninejad, Alireza; Zare, Abdolkarim; Shekouhy, Mohsen; Tetrahedron; vol. 67; 2; (2011); p. 390 – 400;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

74205-82-6, 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 74205-82-6 as follows.

PREPARATION EXAMPLE A (COMPOUND NO. 15) 2-(4-Chloro-2-fluoro-5-ethoxycarbonylmethoxyphenyl)-4, 5,6,7-tetrahydro-2H-isoindole-1,3-dione (4.0 g, made substantially by the methods described in EP 0 083 055 A2) and KOH (85%, 2.1 g) in 50 ml ethanol were stirred at room temperature for 1 hour and then evaporated to dryness. To the residue was added 100 ml chloroform and 8 ml SOCl2. The reaction mixture was then heated to reflux for 2 hours. Potassium chloride was filtered and washed with fresh chloroform. The filtrate was evaporated to dryness. To the residue was added 50 ml chloroform and 1.5 g 1-hydroxymethyl-(1H)-1,2,4-triazole. The reaction mixture was then stirred at room temperature for 5 hours. Water was added to the mixture, the organic layer was separated and washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to give 2.1 g of 2-(4-chloro-2-fluoro-5-[(1,2,4-triazolylmethoxy)carbonylmethoxy]phenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (Compound No. 15). M.P. 151-154 C.

According to the analysis of related databases, 74205-82-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rohm and Haas Company; US6258751; (2001); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

C. (2S,4S)-5-Biphenyl-4-yl-2-hydroxymethyl-4-[(3H-[1,2,3]-triazole-4-carbonyl)-amino]-pentanoic acid 5-methyl-2-oxo-[1,3]-dioxol-4-ylmethyl ester (R7=-CH2-5-methyl-[1,3]-dioxol-2-one) (2S,4S)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-pentanoic acid (75 mg, 190 mumol, 1.0 eq.), HOBt (76 mg, 560 mumol, 3.0 eq.), and EDCI (100 muL, 560 mumol, 3.0 eq.) were dissolved in DCM (2 mL). After stirring for 10 minutes, 4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one (0.2 g, 1.5 mmol, 8.0 eq.) and 4-methylmorpholine (82 muL, 4.0 eq.) were added. The resulting mixture was stirred at room temperature overnight. The mixture was diluted with DCM, and washed with water and saturated aqueous NaCl. The organic layer was collected and concentrated. MeCN (1.9 mL) and 4 M of HCl in dioxane (190 muL, 4.0 eq.) were added and the resulting mixture was stirred at room temperature for 2 hours. The solvent was removed to provide the intermediate HCl salt, which was used in the following coupling step. 1,2,3-Triazole-4-carboxylic acid (25 mg, 220 mumol, 1.2 eq.) and HATU (71 mg, 190 mumol, 1.0 eq.) were dissolved in DMF (1.5 mL), and the resulting solution was stirred for 5 minutes, followed by the addition of DIPEA (650 muL) and the intermediate HCl salt. The reaction was monitored and after 1 hour an additional equivalent of 1,2,3-triazole-4-carboxylic acid, HATU, and DIPEA was added. The reaction was quenched with water and the product purified by preparative HPLC to yield the title compound (39.5 mg; purity 95%). MS m/z [M+H]+ calc’d for C26H26N4O7, 507.18. found 507.4.

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

1001401-62-2, Adding a certain compound to certain chemical reactions, such as: 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic 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 1001401-62-2.

A solution of2-(2H-1,2,3-triazol-2-yl)benzoic acid (P. Coleman, J. Schreier,W02007/126934) (1 g, 4.1 mmol) in SOCb (10 mL) was stirred at 80 C for 30 min. Thesolvent was removed under reduced pressure and toluene (10 mL) was added to give solution A.The product from step 4 (1 g, 4.1 mmol) was dissolved in DCM (10 mL), DIEA (1.58 g, 1225 mmol) added, and then solution A added at 0 C. The resulting mixture was stirred at RT for 2 h,then poured into water (10 mL) and extracted with DCM (10 mL x 3). The combined organiclayers were washed with brine (10 mL), dried overNa2S04, filtered and concentrated in vacuo.The residue was purified by chromatography on silica (petroleum ether : EtOAc = 10 : 1 to = 3 :1) then purified by prep. TLC (petroleum ether: EtOAc = 1 : 1) to give the title compound (0.230 g). LRMS m/z (M+H) 416.0, 418.0 found, 416.1, 418.1 required

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, 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/18029; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

60166-43-0, 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. 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below.

A solution of 1 ,4-dimethyl-1 ,2,3-triazole (0.56 g, 5.77 mmol) in THF (5 ml.) was added dropwise to a solution of BuLi (2.77 ml, 6.92 mmol, 2.5 M in hexane) in 30 mL of THF at -78 0C under N2. The resulting cloudy mixture was stirred at -70 C for 1 h.Then tributyltinchloride (1.711 ml, 6.34 mmol) was added. The reaction mixture became clear and was stirred at this temperature for 30 min, and gradually warmed to rt. To the reaction mixture was added 10 ml of NH4CI and 10 ml of water. The reaction mixture was extracted with ether. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated. The residue was purified on FCC (20% EA/Hexane) to give 1.7 g of a clear liquid (73%). LC-MS (ES) m/z = 388 (M+H)+, 1H NMR (CDCI3, 400 MHz) delta 4.05 (s, 3H), 2.38 (s, 3H), 1.5-0.9 (m, 27H)

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; SMITHKLINE BEECHAM CORPORATION; WO2008/98104; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4922-98-9, 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. 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution of the appropriate 1,2,4-triazole 8a-t (1 mmol)in dry pyridine (5 mL) cooled at ?5 ¡ãC was added 3?,4?,5?-trimethoxybenzoylchloride (252 mg, 1.1 mol, 1.1 equiv.) in small portions. For the preparation of compounds 5u and 5v, 3?,4?-dimethoxybenzoylchloride (221 mg, 1.1 mmol, 1.1 equiv.) or 4?-methoxybenzoyl chloride(188 mg, 1.1 mmol, 1.1 equiv.), respectively, were added to derivative 5k. The reaction mixture was kept for 30 min at ?5 ¡ãC and then overnight at room temperature. Pyridine was removed by evaporation under reduced pressure. To the residue was added CH2Cl2, and the organic phase was washed with saturated aq. NaHCO3, water and brine and dried. The reaction mixture was filtered, and the solvent was removed in vacuo. The crude residue was suspended in ethyl ether(15 mL), the resulting suspension stirred for 30 min, filtered and the residue filtered under reduced pressure to furnish the 1-aroyl-3-aryl-5-amino-1H-1,2,4-triazole derivatives 5a-v. Compounds 5a, 5e, 5f and 5hwere characterized by spectroscopic and analytical data, and our datawere in agreement with those previously reported [30]. 5.1.4.1. (5-Amino-3-phenyl-1H-1,2,4-triazol-1-yl) (3,4,5-trimethoxyphenyl)methanone (5a). Synthesized according to method C, derivative 5a wasobtained as a white solid (yield 66percent); mp 225?227 ¡ãC. 1HNMR(d6-DMSO)delta: 3.80 (s, 3H), 3.87 (s, 6H), 7.47 (m, 3H), 7.68 (s, 2H), 7.86 (bs, 2H), 8.03(m, 2H). 13C NMR (d6-DMSO) delta: 55.96 (2C), 60.13, 108.92 (2C), 126.22(2C), 126.42, 128.70 (2C), 130.02, 130.64, 141.60, 152.00 (2C), 159.05,159.40, 166.39. MS (ESI): [M+1]+=355.37. Anal. calcd forC18H18N4O4. C, 61.01; H, 5.12; N, 15.81; found: C, 60.78; H, 5.01; N,15.67.

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:
Article; Romagnoli, Romeo; Prencipe, Filippo; Oliva, Paola; Baraldi, Stefania; Baraldi, Pier Giovanni; Brancale, Andrea; Ferla, Salvatore; Hamel, Ernest; Bortolozzi, Roberta; Viola, Giampietro; Bioorganic Chemistry; vol. 80; (2018); p. 361 – 374;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics