Month: May 2021

Application of 1186050-58-7, These common heterocyclic compound, 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic 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.

Example 102 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide To a solution of (1S,2S)-1-N-[5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 1; 1.09 g, 3.87 mmol) in DCM (13 ml) was added 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1186050-58-7; 0.802 g, 3.87 mmol), DIPEA (2.027 ml, 11.61 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (0.579 g, 4.26 mmol) and EDC (0.816 g, 4.26 mmol). The reaction was stirred at room temperature for 17 hours and was then partitioned between DCM and a saturated solution of sodium bicarbonate, filtered through a hydrophobic fit and concentrated in vacuo. The residue was purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol) and re-crystallised from IPA to afford the title compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.41-1.59 (m, 2H), 1.59-1.76 (m, 2H), 1.95-2.10 (m, 2H), 4.06-4.20 (m, 2H), 6.68 (d, J=8.8 Hz, 1H), 7.29-7.41 (m, 2H), 7.57-7.66 (m, 2H), 7.71-7.75 (m, 1H), 8.00 (s, 2H), 8.25-8.28 (m, 1H), 8.63 (d, J=6.8 Hz, 1H) MS ES+: 435

The synthetic route of 1186050-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 584-13-4,Some common heterocyclic compound, 584-13-4, name is 4H-1,2,4-Triazol-4-amine, molecular formula is C2H4N4, 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.

Example – 2 4-Amino-1-[3,5-bis-(1-cyano-1-methylethyl)benzyl]-1H-[1,2,4]triazolium bromide (8) (Q. A.-Salt); Isopropanol (1.5 L), 3,5-bis-(1-cyano-1-methylethyl)benzylbromide (2) (100 g) and 4-amino-1,2,4-triazole (22.5 g) were charged in a flask at room temperature. The reaction mass was heated at 80 – 85 C for next 5 hours. The reaction mass was further cooled down to room temperature and stirred for next one hour at 25 – 35 C. The precipitated solid QA-salt was filtered and washed with fresh isopropanol (100 mL x 2). The Q.A.-salt was dried at 60 – 70 C till LOD is less than 1.0 %, giving solid product (74.4 g). m.p.: 198 – 200 C.

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

Reference:
Patent; Cadila Healthcare Limited; EP2397472; (2011); 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., SDS of cas: 4928-87-4

A mixture of l-(7-Amino-5-(-8-azabicyclo[3.2.1]octan-3-yl)-3-(6-phenylpyridin-3- yl)pyrazolo[l,5-a]pyrimidin-6-yl)ethanone (131.4mg, 0.30 mmol), N2H4.H2O (150 ul, 3.0 mmol) in NMP (10 ml) was heated first at 100C for 30 min and then at 200C for 60 min under microwave condition. The mixture was put on rotovap and concentrated at 60C for 2h to remove excess N2H4.H20. lH-l,2,4-triazole-3-carboxylic acid (101.7 mg, 0.90 mmol), EDC (229 mg, 1.20 mmol), HOBt (121.5 mg, 0.90 mmol) and DIEA (521.6 uL, 3.0 mmol) were then added and the mixture was stirred at room temperature for lh. Purification with prep-LC pro ided (( 1 R,3 s,5 S)-3 -(3 -methyl-6-(6-phenylpyridin-3 -yl)- 1 H-dipyrazolo [1,5- a:4′,3′-e]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)(4H-l,2,4-triazol-3-yl)methanone.

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; MERCK SHARP & DOHME CORP.; MENG, Zhaoyang; PATEL, Mehul, F.; SIDDIQUI, M. Arshad; REDDY, Panduranga Adulla, P.; NAN, Yang; WO2013/16164; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 63666-11-5, name is Ethyl 5-amino-4H-[1,2,4]triazole-3-carboxylate, 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. name: Ethyl 5-amino-4H-[1,2,4]triazole-3-carboxylate

Method A. To a suspension of 2-(2,3-dihydro-l -benzofuran-5-yl)-l,3-thiazole-4-carboxylic acid (381 mg, 1.54 mmol) and ethyl 5-amino-l,2,4-triazole-3-carboxylate (219 mg, 1.54 mmol) in 5.4 ml dry pyridine at boiling 2-(lH-benzotriazole-l-yl)-l,l53,3-tetramethyluronium hexafluorophosphate (HBTU) (643 mg, 1.70 mmol) was added in portions while solid dissolves gradually; clear solution forms 5 minutes after all 2-(lH-benzotriazole-l-yl)~l, 1,3,3- tetramethyluronium hexafluorophosphate (HBTU) was added. The solution war kept at stirring at 80 C during 15 h. Pyridine was evaporated to dryness, residue was washed with water, an aqueous NaHC03 solution, water, diluted aqueous AcOH and again water. The residue was dissolved in hot N,N-dimethylfonriamide, filtered, filtrate was evaporated to dryness, the residue was treated with boiling ethanol, cooled and filtered off. The procedure was repeated twice after which the residue was washed with ether and dried to give (339 mg, 0.88 mmol, 57 %) pure product. lE NMR (400 MHz, DMSO-c) delta ppm 14.16 (s, 1H, NH), 11.95 (s, 1H, NH), 8.46 (s, 1H, CH-thiazole), 8.08 (s, 1H, CH-Ar), 7.88 (d, J = 8.2 Hz, 1H, CH-Ar), 6.84 (d, J = 8.3 Hz, 1H, CH-Ar), 4.65 (t, J = 8.7 Hz, 2H, OCH2CH2), 4.34 (q, J = 7.0 Hz, 2H, OCH2CH3), 3.30 (t, J = 8.7 Hz, 1H, OCH2CH2), 1.37 (t, J = 7.1 Hz, 3H, OCCH3). LC/MS [M+H]+: 386.0

The synthetic route of Ethyl 5-amino-4H-[1,2,4]triazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 4SC DISCOVERY GMBH; LEBAN, Johann; ZAJA, Mirko; WO2014/202638; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-70-2, name is 1H-[1,2,3]Triazole-4-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. Quality Control of 1H-[1,2,3]Triazole-4-carboxylic acid

N. (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid pentyl ester (R4=H; R7=-(CH2)4CH3) (2S,4R)-4-Amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid (76 mg, 242 mumol) in MeCN (0.4 mL, 8 mmol) and 4 M HCl in 1,4-dioxane (242 muL, 969 mumol) was combined with pentan-1-ol (0.5 mL) at 60 C. The resulting mixture was stirred until solid precipitation was observed (~30 minutes). The solvent was evaporated under vacuum and the solids were azeotroped in toluene and dried under vacuum. 1,2,3-Triazole-4-carboxylic acid (0.0274 g, 0.242 mmol), DIPEA (169 muL, 969 mumol) and HATU (92 mg, 242 mumol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with the dried solids, predissolved in DMF (0.2 mL) and DIPEA (0.5 eq.). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product was purified by preparative HPLC and lyophilized to yield the title compound (30 mg; purity 95%). MS m/z [M+H]+ calc’d for C27H34N4O4, 479.26. found 479.4.

The synthetic route of 16681-70-2 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

Synthetic Route of 3641-13-2, These common heterocyclic compound, 3641-13-2, name is 5-Amino-4H-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.

General procedure: A mixture of benzil (0.01 mol), aldehydes (0.01 mol), 3-amino-1,2,4-triazole-5-carboxylic acid (0.01 mol), ammonium acetate (0.01 mol) and ceric ammonium nitrate (15 mol%) as a catalyst were refluxed in ethanol (15 mL) for about 3-4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was cooled to room temperature. The solid formed was filtered and dried. The crude products were recrystallized by ethanol.

Statistics shows that 5-Amino-4H-1,2,4-triazole-3-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 3641-13-2.

Reference:
Article; Nikalje, Anna Pratima G.; Ghodke, Mangesh S.; Kalam Khan, Firoz A.; Sangshetti, Jaiprakash N.; Chinese Chemical Letters; vol. 26; 1; (2015); p. 108 – 112;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 4923-01-7,Some common heterocyclic compound, 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, molecular formula is C3H6N4, 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: Method I. A mixture of Py (4.4 ml) and AcOH (3.0 ml) was stirred and treated by the addition of 5-aminoazole1a-h (0.01 mol) and (2E)-(3-morpholin-4-yl)-acrylonitrile (2) (1.38 g, 0.01 mol). The obtained mixture was refluxed at 150C for 5 h. After refluxing, the mixture was cooled. The precipitate that formed was filtered off, washed with a small amount of EtOH, and dried. Method II. A solution (or suspension) of the appropriate aminoazole 1a-h (0.01 mol) in solvent (15 ml) (EtOH in the case of compound 3a, dioxane in the case of compounds 3b-h) was stirred at 50C and treated by adding 3,3-diethoxypropionitrile (4) (1.5 ml, 0.01 mol), then 36% HCl solution (0.86 ml, 0.01 mol). The reaction mixture was refluxed for 2.5-3 h, the suspension (or solution) was cooled to room temperature, and the target product was isolated by the method indicated for each particular compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-4H-1,2,4-triazol-3-amine, its application will become more common.

Reference:
Article; Gazizov, Denis A.; Fedotov, Victor V.; Gorbunov, Evgeny B.; Ulomskiy, Evgeny N.; Yeltsov, Oleg S.; Rusinov, Gennady L.; Rusinov, Vladimir L.; Chemistry of Heterocyclic Compounds; vol. 55; 6; (2019); p. 573 – 577; Khim. Geterotsikl. Soedin.; vol. 55; 6; (2019); p. 573 – 577,5;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-70-2, A common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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.

1,2,3-Triazole-4-carboxylic acid (14 mg, 124 mumol), DIPEA (86.3 muL, 496 mumol) and HATU (47.1 mg, 124 mumol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester (57.2 mg, 124 mumol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product purified by preparative HPLC and lyophilized to yield the title compound (19 mg; purity 95%). MS m/z [M+H]+ calc’d for C31H32N4O6, 557.23. found 557.2.

The synthetic route of 16681-70-2 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

Related Products of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

[00302] To a solution of N1 -(2-chloro-6-phenylpyrimidin-4-yl)cyclohexane- 1,3 -diamine (65 mg, 0.21 mmol) in a mixed solvent of tetrahydrofuran (4 mL) and dimethyl sulfoxide (1 mL) were added N,N-diisopropylethylamine (0.11 mL, 0.7 mmol) and 1H-1,2,3-triazole-4-carboxylic acid (48 mg, 0.42 mmol). The mixture was stirred at rt for 10 mm, then HATU (163 mg, 0.43 mmol) was added, and the resulting mixture was stirred at rt for 3 hours. To the reaction mixture was added water (10 mL), and the resulting mixture was extracted with ethyl acetate (10 mL x 3). The combined organic layers were washed with saturated brine (30 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound as a colorless solid (85 mg, 100%).MS (ESI, pos.ion) m/z: 398.5 [M+H].

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
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. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C4H5N3O2

EXAMPLES; Synthesis of the methyl ester of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid (triacetylribavirin, 3-carbomethoxy, TARC, IV, PG=CH3CO, R2=COOCH3); In a 6000 ml, 4-neck anhydrous reactor equipped with thermometer, condenser and mechanical stirrer, there are placed, while stirring and with a flow of nitrogen, 1680 ml of dichloromethane, 400 g of tetra-acetylribose (Fluka) and 185.2 g of 3-carbomethoxytriazole. The mixture is cooled to about 5°C and 360 g of tin tetrachloride are added to the suspension in a thin stream while stirring. The exothermy of the reaction is controlled by cooling with an ice bath so that the temperature does not exceed 15-20°C and, when the addition is finished, the reaction mixture is heated to reflux for 2 hours. It is cooled to 20°C with a water and ice bath in 15 minutes. Then 30percent hydrochloric acid (176.7 ml) and water (1503.3 ml) are added at a temperature below +20°C and stirring is carried out for 45 minutes; the mixture is left to dephase for 15 minutes, then the upper aqueous phase is separated from the rich organic phase which is subsequently treated with 30percent hydrochloric acid (176.7 ml) and water (1503.3 ml). After 45 minutes’ stirring, the mixture is left to dephase for 15 minutes and the upper aqueous phase is separated from the rich organic phase, which is subsequently treated with 30percent hydrochloric acid (176.7 ml) and water (1503.3 ml). After 45 minutes’ stirring, the mixture is left to dephase for 15 minutes and the phases are separated: the organic phase is distilled at atmospheric pressure (internal T approx. 45°C), and to the oily residue 3000 ml of toluene are added and the mixture is distilled under vacuum at about 200 mbar of residual pressure to a stirrable moist paste. It is cooled to 5-10°C for 2 hours and filtered over a Buchner filter while washing with toluene. 524 g of moist product are obtained, equal to 392 g dry product.

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; Clariant Life Science Molecules (Italia) SpA; EP1281715; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics