Triazoles

Some common heterocyclic compound, 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, molecular formula is C3H4N4O2, 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. HPLC of Formula: C3H4N4O2

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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3641-13-2, its application will become more common.

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 16681-65-5, These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-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.

A solution of n-BuLi (3.8 mL, 9.5 mmol, 2.5 M solution in hexane) was added slowly to a solution of 1-methyl-1H-1,2,3-triazole (0.83 g, 10 mmol) in THF (48 mL) at -50 C. After addition, stirring was continued for an additional 30 minutes and N-methoxy-N,2,6-trimethylisonicotinamide (0.97 g, 5.0 mmol, Intermediate 29: step a) dissolved in THF (12 mL) was slowly added. An additional 2 mL of THF was used to complete the quantitative addition. The mixture was stirred at -50 C. for 5 minutes then warmed to room temperature and stirred overnight. The solution was quenched with saturated aqueous NH4Cl. H2O was added and layers were separated. The aqueous layer was extracted with EtOAc and the combined organic extracts washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified using flash column chromatography (0 to 100% EtOAc/DCM) to provide the title compound.

The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); 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 7170-01-6 as follows. Recommanded Product: 7170-01-6

To a solution of 2-chloropyrimidine-5–carbaldehyde (0.25 g, 1.75 mmol) in THF (7 rnL) was added K2C03 (0.36 g, 2.63 mmol) and 3-methyi-1T-1-i,2,4-1riazoie (022 g, 2.63 mmoi). The resulting mixture was stirred at 70 0Q for 2 h. The reaction mixture was cooled to ambient temperature and poured into ice cold water (30 mL) and extracted with ethyl acetate (2 x 50 mL).The combined organic layers were washed with brine (20 mL), dried over sodium sulfate and distilled under reduced pressure. The residue was recrystallised from DCM/n-hexane to obtain Intermediate 105 (0300 g, 7050%) as yellow sticky material, ?HNMR (400 MHz, DMSO-d6) oepprn 2.34 2.43 (rn, 3 H), 9.29 – 9.40(m, 2H), 10.10- 10.25 (m, I H), 13.69(br. s., I H). LCMS (Zvlethod-D): retention time 0.42 mm, [M+ii 190.2.

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 74205-82-6, The chemical industry reduces the impact on the environment during synthesis 74205-82-6, name is (1H-1,2,4-Triazol-1-yl)methanol, I believe this compound will play a more active role in future production and life.

The indoline (1) (10.0 (^, 0.08311101) was added to a 11 round bottom flask, Glacial acetic acid 1001111, stirring at room temperature 0.5h, adding triazole methyl alcohol (16.61 g, 0.167 mol), and the reaction was stirred at 80 C for 3 h. TLC indicated that the reaction was complete and stopped The reaction was cooled to room temperature, 40% aqueous sodium hydroxide (100 ml) and 100 ml of methanol were added under ice-cooling, refluxed for 0.5 h at 70 C, Dichloromethane (75 mL x 3), saturated brine (150 ml x 2), dried over anhydrous sodium sulfate and concentrated to give Yellow oil 7.74 g (2), yield 46.6%

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, (1H-1,2,4-Triazol-1-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan University; Wu, Yong; Guan, mei; Zhao, yinbo; Hai, Li; He, Yi; Li, Xiao Cen; (9 pag.)CN103664901; (2016); B;,
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. Product Details of 4928-87-4

A mixture of 3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)-8,9- dihydropyrazolo[l,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one (70 mg, 0.17 mmoL), 1H- 1,2,4- triazole-3-carboxylic acid (20.5 mg, 0.18 mmoL), EDC (63 mg, 0.33mmoL), HOBt (44.6 mg, 0.33 mmoL) and DIEA (172.2 uL, 0.99 mmoL) in DMF (3 mL) was stirred at room temperature for 2h. Purification with prep-LC provided 5-(l-(4H-l ,2,4-triazole-3- carbonyl)piperidin-4-yl)-3~(6-phenylpyridin-3-yl)-8,9-dihydropyrazolo[l,5-a]pyrido[3s2- e]pyrimidin-6(7H)-one: LCMS tR = 3.15 Min (10 rain run, UV 254nm)- Mass calculated for, M+ 519.2, observed LC/MS m/z 519.97 (M+H).

The synthetic route of 4928-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; MENG, Zhaoyang; REDDY, Panduranga Adulla, P.; SIDDIQUI, M. Arshad; MANDAL, Amit, K.; LIU, Duan; ZHAO, Lianyun; MCRINER, Andrew; WO2012/27234; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1533519-85-5, These common heterocyclic compound, 1533519-85-5, name is Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, 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.

Into a 1L three-necked flask, add 20.0g of intermediate (4), 80ml of tetrahydrofuran and 20ml of methanol, start stirring, warm up to 40.0C, stir until dissolved; add 20.0g NBS, 0.2g TEMPO, react for 60min; cool to 5C, add ethyl acetate 100ml and purified water 120ml, the organic phase was washed with 120ml of 3% sodium bisulfite solution and 100ml of 5% sodium bicarbonate solution, dried with anhydrous sodium sulfate 50.0g, filtered, rinsed with ethyl acetate 50ml, the mother liquor was concentrated to dryness, 60ml of ethyl acetate was added to the residue, heated until the solid was dissolved, 240ml of n-hexane was added, and the temperature was slowly lowered to 0-5C, filtered, washed, and dried to obtain 22.0g of off-white solid with a yield of 89.4%.

Statistics shows that Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate is playing an increasingly important role. we look forward to future research findings about 1533519-85-5.

Reference:
Patent; Beijing Xinkaiyuan Pharmaceutical Technology Co., Ltd. Hainan Fen Corporation; Xia Zhongning; Wu Jin; Bai Bingxin; (9 pag.)CN111116501; (2020); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, name is 3-Methyl-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. Formula: C3H5N3

Synthesis of 3-methoxy-4-(3-methyl-1H-[1,2,4]triazol-1-yl)benzaldehyde A solution of 3-methyl-1H-[1,2,4]triazole [described in] (383 mg) and 4-fluoro-3-methoxybenzaldehyde (711 mg) in DMF (10 mL) was stirred at 90C overnight. Then, potassium carbonate (1.20 g) was added to the reaction solution, and the reaction solution was stirred at 110C for 6.5 hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 82.5 mg of the title compound. The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 2.50 (s, 3H), 4.05 (s, 3H), 7.59 (d, J = 8.4 Hz, 1H), 7.60 (s, 1H), 8.07 (d, J = 8.4 Hz, 1H), 8.84 (s, 1H), 9.99 (s, 1H).

The synthetic route of 7170-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2019094; (2009); 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. category: Triazoles

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 methoxycarbonylmethyl ester (47.8 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 (18 mg; purity 95%). MS m/z [M+H]+ calc’d for C25H28N4O6, 481.20. found 481.2.

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

Electric Literature of 27808-16-8, A common heterocyclic compound, 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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.

A solution of 4-methyl-iH-i,2,3-triazole (500 mg,6.02 mmol), 2,3-dichloro-5-nitropyridine (1277.42 mg, 6.62 mmol), K2C03 (2491.22 mg, 18.05 mmol) in CH3CN (5 mE) was stirred at it for 12 h. The mixture was concentrated under reduced pressure, the crude product was purified by colunm chromatography over silica gel (petroleum ether ethyl acetate from 20:1 to 1:1). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford i25a (1.1 g, 76.3%) as a yellow solid. ECMS (ESI) mlz M+i: 239.7. Zn (1491.96 mg, 22.95 mmol) was added to a solution of mixture of 3-chloro-2-(4-methyl-2H-i,2,3-tri- azol-2-yl)-5-nitropyridine and 3-chloro-2-(4-methyl-i H-i, 2,3-triazol-i-yl)-5-nitropyridine, i25a (1.1 g, 2.30 mmol) in aqNH4C1 (30 mE) and H20 (30 mE). The mixture was stirred at it for 16 h. To the suspension was added aq NaHCO3 to adjust to pH 9-10, and the mixture was filtered through a pad of diatomaceous earth. The filter cake was washed with CH2C12 (100 mEx3). The combined filtrates were washed with brine (200 mE), dried over MgSO4 and concentrated under reduced pressure to afford mixture of 5-chloro-6-(4-methyl-2H- 1 ,2,3-triazol-2-yl)pyridin-3-amine and 5-chloro-6-(4-methyl-i H-i ,2,3-triazol- 1 -yl)pyriF din-3-amine, 125b (1 g) as a brown solid, used directly for the next step. LCMS (ESI) mlz M+H: 209.7 P0C13 (182.86 mg, 1.19 mmol) was added to a solution of 125b (300 mg, 0.72 mmol), 1-(quinolin-5-yl)-5- (trifluoromethyl)-1 H-pyrazole-4-carboxylic acid (183.19 mg, 0.60 mmol), pyridine (117.91 mg 1.49 mmol) in CH2C12 (10 mE). The mixture was stirred at it for 2h, 50 mE H20 and 50 mE CH2C12 were added to the mixture. The organic layer was washed with brine (50 mE), dried over MgSO4 and concentrated under reduced pressure to afford the crude product, which was purified by preparative HPEC (35% to 65% (v/v) CH3CN and H20 with 0.05% HC1) and lyophilized to dryness to afford the title compound (208 mg 69.8% yield) as a white solid. ECMS (ESI) mlz M+1: 499.0. ?H NMR (400 MHz, DMSO-d5) oe ppm 11.45 (s, 1H), 9.06 (t, J=2.54 Hz, 1H), 8.89 (s, 1H), 8.60-8.75 (m, 2H), 8.33 (d, J=8.38 Hz, 1H), 7.88-8.03 (m, 3H), 7.68 (d, J=2.65 Hz, 2H), 2.34 (s, 3H).

The synthetic route of 27808-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-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. name: 1-Methyl-1H-1,2,3-triazole

A solution of n-BuLi (0.37 mL, 0.92 mmol, 2.5 M solution in hexane) was added slowly to a solution of 1-methyl-1H-1,2,3-triazole (79.7 mg, 0.959 mmol) in THF (10 mL) at -50 C. After addition, stirring was continued for an additional 30 minutes at -50 C. and (4-chloro-2-methoxy-3-((3-(trifluoromethyl)azetidin-1-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (Intermediate 52, 182 mg, 0.402 mmol) dissolved in THF (4 mL) was slowly added. An additional 2 mL of THF was used to complete the quantitative addition. The mixture was stirred at -50 C. for 10 minutes then warmed to room temperature and stirred for 18 hours. The solution was quenched with saturated aqueous NH4Cl solution. H2O was added and layers were separated. The aqueous layer was extracted with EtOAc and the combined organic extracts washed with brine, dried over MgSO4, filtered, evaporated in vacuo. The crude product was purified using flash column chromatography (0 to 7% MeOH-DCM) to provide the title compound. MS m/e 536.1 (M+H)+.

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

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics