Tag: M.W:100-200

Adding some certain compound to certain chemical reactions, such as: 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, 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 4928-87-4. 4928-87-4

To a reaction of H-, 2, 4-triazole-3 -carboxylic acid (226 mg, 2.0 mmol) and 3- methoxybenzylamine (0.28 mL, 2.2 mmol) in dry DMF (10 mL) was added 1- hydroxybenzotriazole monohydrate (337 mg, 2.2 mmol) and EDC (N-(3- Dimethylaminopropyl)-N’-ethylcarbodiimide) (422 mg, 2.2 mmol) followed by N- methylmorpholine (0.88 mL, 8.0 mmol via syringe). The mixture was stirred at room temperature under nitrogen and the solids were gradually dissolved. The contents were stirred at room temperature for 24.0 h, and then slowly diluted into iced water and extracted with DCM (2 x 50 mL). The DCM phase was washed with ice cold water (2 x 100 mL). The DCM phase was dried over anhydrous Na2S04, concentrated under reduced pressure and chromatographed on silica gel using MeOH and DCM (2:98) as eluents to get the desired amide 7 (170.9 mg, 37 % yield) as a white solid compound. -NMR (400 MHz, DMSO-de): <514.76-14.65 (m, 1H), 9.15 (br s, 1H), 8.48 (br s, 1H), 7.23 (t, J= 8 Hz, 1H), 6.90-6.88 (m, 2H), 6.82-6.80 (m, 1H), 4.43 (d, J= 6 Hz, 2H), 3.73 (s, 3H) ppm. MH+ = 233.2 m/z. 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 1,2,4-Triazole-3-carboxylic acid. Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; NATIONAL JEWISH HEALTH; WEMPE, Michael Fitzpatrick; VAZQUEZ-TORRES, Andres; DAI, Shaodong; (72 pag.)WO2020/41556; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4314-22-1, name is 2-(1H-1,2,3-Triazol-1-yl)acetic 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. 4314-22-1

To a stirred mixture of 5 (65 mg, 0.173 mmol), 1 – 1 ,2,3-triazoleacetic acid (6, 22 mg, 0.173 mmol), and Hunig’s base (0.091 mL, 0.522 mmol) in DMF (2 ml) was added HATU (66 mg, 0.174 mmol) and the reaction mixture was stirred for 30 min. The crude mixture was directly purified by prep. HPLC to give 7 (39 mg, 46%). -NMR (400MHz, d6-DMSO): 513.0 (s, IH), 8.34 (bs, IH), 8.16-8.1 1 (m, 2H), 8.00-7.95 (m, 2H), 7.71 (s, IH), 7.55-7.42 (m, 2H), 7.19 (q, IH), 5.51-5.43 (2s, 2H), 4.86-4.83 (m, 2H), 3.81-3.52 (m, 4H), 3.13-3.12 (2s, 3H), 3.04-2.97 (2s, 3H), 2.64-2.63 (2s, 3H). MS (EI) for C24H27N, ,0, found 486 (MH+).

Statistics shows that 4314-22-1 is playing an increasingly important role. we look forward to future research findings about 2-(1H-1,2,3-Triazol-1-yl)acetic acid.

Reference:
Patent; EXELIXIS, INC.; LEAHY, James, William; WO2012/37204; (2012); 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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., 4928-87-4

The intermediate 27a was added(0.2 g, 0.39 mmol) was dissolved in 35 ml of DMF, EDCI (0.08 g, 0.42 mmol) was added,HOBT, (0.058, 0.38 mmol) was dissolved with stirring, and then ml, 2,4-triazole-3-carboxylic acid (0.058,0.44mmo 1), DIEA 0.2ml (1.17mmo 1), stirring at room temperature for 12h, TLC detection, the end of the reaction, the liquid spin dry crude, crudeThe product was purified by silica gel G column chromatography [eluent (methanol: dichloromethane) = 50: 500 (nu: nu)] to give the title compound0 ¡¤ 08g, yield 33.3%

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; Beijing Foreland Pharma Co., Ltd; Zhang, Xingmin; Wang, Ensi; Niu, Shengxiu; Guo, Jing; Dai, Zhuolin; Zheng, Nan; Ji, Qi; Li, Qinyan; Liang, Tie; (109 pag.)CN104411706; (2016); B;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, Adding some certain compound to certain chemical reactions, such as: 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, 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 4928-87-4.

To a reaction of 1/7-1, 2, 4-triazole-3 -carboxylic acid (113 mg, 1.19 mmol) and 3- (trifluoromethoxy)benzylamine (250 mg, 1.31 mmol) in dry DMF (10 mL) was added 1- hydroxybenzotriazole monohydrate (200 mg, 1.31 mmol) and EDC (N-(3- Dimethylaminopropyl)-N’- ethylcarbodiimide) (251 mg, 1.31 mmol) followed by N- methylmorpholine (0.52 mL, 4.76 mmol via syringe). The mixture was stirred at room temperature under nitrogen and the solids were gradually dissolved. The contents were stirred at room temperature for 24.0 h, and then slowly diluted into iced water and extracted with DCM (2 x 50 mL). The DCM phase was washed with ice cold water (2 x 100 mL). The DCM phase was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure and chromatographed on silica gel using DCM and EtOAc (10:90) as eluents to get the desired amide 9 (108.7 mg, 32 % yield) as a white solid compound. -NMR (400 MHz, DMSO-de): <514.67 (br s, 1H), 9.28 (br s, 1H), 8.53 (br s, 1H), 7.48- 7.44 (m, 1H), 7.36-7.34 (m, 1H), 7.30 (br s, 1H), 7.24-7.22 (m, 1H), 4.50 (d, J= 6.4 Hz, 2H); 19F -NMR (376 MHz, DMSO-de): <5 -56.70 ppm. MH+ = 287.2 m/z. 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 4928-87-4. Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; NATIONAL JEWISH HEALTH; WEMPE, Michael Fitzpatrick; VAZQUEZ-TORRES, Andres; DAI, Shaodong; (72 pag.)WO2020/41556; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-33-1, name is 5-Bromo-1H-1,2,4-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. 7343-33-1

Example 6 Preparation of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol), and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 mL) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100¡ã C. for 36 h. The reaction mixture was cooled to room temperature, diluted with EtOAc, filtered through a plug of Celite? and further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography (EtOAc/hexanes) yielded the title compound as an off white solid (3.78 g, 72.6percent): mp 67-69¡ã C.; 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H), 7.70 (m, 2H), 7.38 (m, 2H); 19F NMR (376 MHz, CDCl3) delta -58.02. Example 5 Preparation of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with potassium phosphate (K3PO4, 7.74 g, 36.5 mmol), CuI (0.165 g, 0.868 mmol), and 3-bromo-1H-1,2,4-triazole (2.83 g, 19.10 mmol). The flask was evacuated/backfilled with N2 (3*). DMF (34.7 mL) was added, followed by trans-(1R,2R)-N,N’-bismethyl-1,2-cyclohexane diamine (0.274 ml, 1.736 mmol) and 1-iodo-4-(trifluoromethoxy)benzene (5.000 g, 17.36 mmol). The solution was heated to 110¡ã C. After 48 h, the reaction mixture was cooled to room temperature, diluted with EtOAc and filtered through Celite?. The filtrate was washed with water (100 mL) containing HCl (1 M, 10 mL. The organics were separated, and the aqueous phase was further extracted with EtOAc (3*). The organics were combined, dried, and concentrated in vacuo. Purification via flash column chromatography (EtOAc/hexanes) yielded the title compound as a tan solid (1.86 g, 34percent): 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta -58.04; EIMS m/z 307.

Statistics shows that 7343-33-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-1H-1,2,4-triazole.

Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CREEMER, Lawrence C.; CROUSE, Gary D.; US2014/275502; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, These common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, 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 reaction of 1/7-1, 2, 4-triazole-3 -carboxylic acid (226 mg, 2.0 mmol) and (R)- (+)-a-methyl benzyl amine (0.27 mL, 2.1 mmol) in dry DMF (10 mL) was added 1- hydroxybenzotriazole monohydrate (337 mg, 2.2 mmol) and EDC (N-(3- Dimethylaminopropyl)-N’-ethylcarbodiimide) (422 mg, 2.2 mmol) followed by N- methylmorpholine (0.88 mL, 8.0 mmol via syringe). The mixture was stirred at room temperature under nitrogen and the solids were gradually dissolved. The contents were stirred at room temperature for 24.0 h, and then slowly diluted into iced water and extracted with DCM (2 x 50 mL). The DCM phase was washed with ice cold water (2 x 100 mL). The DCM phase was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure and chromatographed on silica gel using EtOAc and Hexanes (75:25) as eluents to get the desired amide 17 (88 mg, 20 % yield) as a white solid compound. -NMR (400 MHz, DMSO-de): 1H), 7.42-7.40 (m, 2H), 7.34-7.30 (m, 2H), 7.25-7.21 (m, 1H), 5.19-5.12 (m, 1H), 1.50 (d, J= 6.8 Hz, 3H) ppm. MH+ = 217.1 m/z.

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 4928-87-4.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; NATIONAL JEWISH HEALTH; WEMPE, Michael Fitzpatrick; VAZQUEZ-TORRES, Andres; DAI, Shaodong; (72 pag.)WO2020/41556; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

252742-72-6, Name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, 252742-72-6, 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.

Example 408 5-[4-(2-(2-Fluorophenyl)acetyl]piperidino]methyl-2,4-dihydro-[1,2,4]triazol-3-one After adding 150 mg of 5-chloromethyl-2,4-dihydro-[1,2,4]triazol-3-one, 335 mg of 2-(2-fluorophenyl)-1-(piperidin-4-yl)ethanone hydrochloride and 180 mg of anhydrous potassium carbonate to acetonitrile, the mixture was stirred overnight at room temperature. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Diethyl ether was added to the residue and the mixture was filtered to obtain the title compound (23 mg, 7percent yield). 1H-NMR (400 MHz, DMSO-d6); delta (ppm) 1.42-1.56 (2H, m), 1.79-1.87 (2H, m), 1.98-2.07 (2H, m), 2.45-2.55 (1H, m), 2.75-2.82 (2H, m), 3.25 (2H, s), 3.89 (2H, s), 7.09-7.16 (2H, m), 7.19-7.32 (2H, m), 11.20 (1H, s), 11.26 (1H, br s).

Statistics shows that 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one is playing an increasingly important role. we look forward to future research findings about 252742-72-6.

Reference:
Patent; Ozaki, Fumihiro; Ono, Mutsuko; Kawano, Koki; Norimine, Yoshihiko; Onogi, Tatsuhiro; Yoshinaga, Takashi; Kobayashi, Kiyoaki; Suzuki, Hiroyuki; Minami, Hiroe; Sawada, Kohei; US2004/167224; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

6523-49-5, 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. 6523-49-5 name is 4-(1,2,4-Triazol-1-yl)aniline, 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.

A mixture of the formamidine from step 1 (304 mg) and 4-triazolylaniline (75 mg) in AcOH (2 ml) was heated to 125 for 1.5 h. After cooling, the mixture was diluted and basified with IN NaOH (20 ml). The resulting ppt was isolated by filtration and dried to give the title compound (136 mg, 71 %) as a yellow solid.1H NMR delta 10.07 (IH3 s), 9.28 (IH, s), 8.78 (IH, s), 8.62 (lH,s), 8.25 (IH, s), 8.16 (IH, d, J 8.85Hz), 8.07 (2H, d, J 8.85Hz), 7.86 (2H, d, J 8.85Hz), 7.82 (IH, d, J 8.85Hz), 7.47 (IH, d, J 1.9Hz), 7.38 (IH, dd, J 8.2, 1.9Hz), 7.03 (IH, d, J 8.85Hz) 4.32 (4H, s); LC-MS rt 2.35 m/z 423 ES+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1,2,4-Triazol-1-yl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, name is 1,2,4-Triazole-3-carboxylic 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. 4928-87-4

Step 7: Preparation of ((lR,3s,5S)-3-(8-amino-3-(6-phenylpyridin-3-yl)imidazo[l,2-a]pyrazin- 6-yl)-8-azabicyclo[3.2.1]octan-8-yl)(4H-l ,2,4-triazol-3-yl)methanone A mixture of crude 6-((lR,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl)-3-(6-phenylpyridin- 3-yl)imidazo[l,2-a]pyrazin-8-amine from step 7, lH-l ,2,4-triazole-3-carboxylic acid (33.0 mg, 0.29 mmol), EDCI (92.9 mg, 0.49 mmol), 1-hydroxybenzotriazole (65.6 mg, 0.49 mmol) and DIEA (253 ul, 1.46 mmol) in DMF (5 mL) was stirred at room temperature for lh.Purification with prep-LC and conversion to HCl salt provided ((lR,3s,5S)-3-(8-amino-3-(6- phenylpyridin-3-yl)imidazo[l,2-a]pyrazin-6-yl)-8-azabicyclo[3.2.1]octan-8-yl)(4H-l ,2,4- triazol-3-yl)methanone as HCl salt: LCMS tR = 2.25 Min (10 min run, UV254nm). Mass calculated for, M+ 491.2, observed m/z 492.3 (M+H).

Statistics shows that 4928-87-4 is playing an increasingly important role. we look forward to future research findings about 1,2,4-Triazole-3-carboxylic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MENG, Zhaoyang; SIDDIQUI, M. Arshad; REDDY, Panduranga Adulla, P.; WO2013/16160; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 6818-99-1, name is 3-Chloro-1,2,4-triazole, I believe this compound will play a more active role in future production and life. 6818-99-1

A solution of 4-[5-(6-chloro-3-ethylsulfonyl-2-pyridyl)-4-methyl-1 ,2,4-triazol-3-yl]-6-(trifluoromethyl) pyrimidine (300 mg, 0.693 mmol) and 3-chloro-1 H-1 ,2,4-triazole (107.6 mg, 1.04 mmol) in pyridine (3 ml) unter argon was heated in the microwave at 120C for 30 minutes. After cooling, the reaction mixture was poured onto iced water (20 ml), the suspension filtered and the solid washed with cold water. This residue was dissolved in dichloromethane, dried over sodium sulfate, filtered and concentrated to dryness to afford the title compound 4-[5-[6-(3-chloro-1 ,2,4-triazol-1-yl)-3-ethylsulfonyl-2- pyridyl]-4-methyl-1 ,2,4-triazol-3-yl]-6-(trifluoromethyl)pyrimidine (compound P48) as a solid, mp 261- 263C. LCMS (method 1 ): 500/502 (M+H)+; retention time: 0.96 min. H-NMR (CDCI3, ppm) 1.38 (t, 3H), 3.72 (q, 2H), 4.14 (s, 3H), 8.25 (d, 1 H), 8.73 (d, 1 H), 8.79 (s, 1 H), 9.07 (s, 1 H), 9.48 (s, 1 H).

The chemical industry reduces the impact on the environment during synthesis 6818-99-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; EMERY, Daniel; BUCHHOLZ, Anke; (145 pag.)WO2017/16910; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics