Category: Triazoles

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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Methyl-1H-1,2,3-triazole

To a flask containing 1-methyl-1H-1,2,3-triazole (275 mg, 3.31 mmol, prepared according to PCT Int. Appl., 2008098104) was added THF (35 mL) and the colorless solution was cooled to -50 C. Then, n-butyllithium (2.5 M in hexanes, 1.2 mL, 3.0 mmol) was added dropwise which afforded a dark reddish-brown viscous solution. The mixture was stirred between -20 to -10 C. for 30 minutes, then a homogeneous THF solution of (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone (700 mg, 1.44 mmol in 4 mL THF, Intermediate 12: step f) was introduced at 0 C. The reaction mixture became a dark brown color and was allowed to warm gradually to room temperature. The mixture was stirred for 60 minutes at room temperature then quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc, 3*50 mL. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to provide a brown oil. Chromatography on silica gel (1% MeOH-DCM increasing to 5% MeOH-DCM) provided the title compound as a light brown solid. Racemic (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol was separated into its individual enantiomers using the following conditions: Chiralcel OD, 20 uM (Diacel) using ethanol with 242 nM detection to give the first eluting enantiomer as Intermediate 84b and the second eluting enantiomer as Intermediate 84c.

According to the analysis of related databases, 16681-65-5, the application of this compound in the production field has become more and more popular.

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

Adding a certain compound to certain chemical reactions, such as: 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, 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 103755-58-4, name: (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol

Methyl iodide (7.34g, 3.24mL, 51.72mmol, 6equiv.) was added to acetonitrile (10mL) solution of triazole 1 (1.5g, 8.62mmol, 1equiv.) and heated in a teflon lined sealed steel vessel at 80C for 36h. After completion of reaction, solvent was removed under vacuo and washed with ethyl acetate (5¡Á10mL) to give pale yellow crystalline solid in (2.25g) 83% yield. Mp: 140-142C; IR (KBr): 3316 (nuOH), 1597, 1077cm-1; 1H NMR (400MHz, CDCl3) delta: 9.35 (s, 1H), 7.92-7.90 (m, 2H), 7.65-7.63 (m, 3H), 5.15 (d, 2H, J=6Hz), 5.00 (t, 1H, J=6Hz), 4.51 (s, 3H); 13C NMR (100MHz, CDCl3) delta: 145.0, 134.7, 132.2, 130.7, 128.4, 121.7, 53.0 (-CH2-OH), 40.0 (-CH3-N); HRMS (ESI-MS) calcd for C10H13N3O [M+H]+ 191.1059, found 191.1067.

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

Reference:
Short Survey; Saravanakumar, Rajendran; Ramkumar, Venkatachalam; Sankararaman, Sethuraman; Journal of Organometallic Chemistry; vol. 736; (2013); p. 36 – 41;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. Application In Synthesis of 1H-[1,2,3]Triazole-4-carboxylic acid

[0833] lH-1,2,3-triazole-4-carboxylic acid (3.8 mg, 34f.tmol)was combined withHATU (12.9 mg, 34 flillOI) inDMF(2 mL) and stirred at room temperature for 15 minutes. Compound3(60mg, 137 f.tmol)andDIPEA(l6f.LL, 92f.tmol)werethen added. The solution was stirred at room temperature for15 minutes, at which time LCMS showed reaction completion.The solvent was removed in vacuo and the crude residuewas purified by reverse phase chromatography to yield Compoundb (18.5 mg) as a TFA salt. MS m/z [M+Hr calc’d forC26H31CIFN50 4 , 532.21. found 532.

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 288-36-8, These common heterocyclic compound, 288-36-8, name is 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.

Into a 3000-mL 3-necked round-bottom flask, was placed 2H-1,2,3-triazole (100 g, 1.45 mol, 1.00 equiv), water (1000 mL), Br2 (522 g, 3.27 mol, 2.25 equiv). The resulting solution was stirred overnight at 50 C. in an oil bath. The reaction was then quenched by the addition of 1000 mL of Na2SO3 (aq). The solid was collected by filtration and dried in an oven under reduced pressure. This resulted in 313 g (95%) of 4,5-dibromo-2H-1,2,3-triazole as a white solid.

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Apollo, LLC; Ghosh, Shomir; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Leit De Moradei, Silvana Marcel; (290 pag.)US2017/166584; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 13273-53-5, These common heterocyclic compound, 13273-53-5, name is 4-Bromo-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 mixture of tert-butyl 4-({[2-amino-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (I-55) (580 mg, 1 .34 mmol), 4-bromo-1 -methyl-1 /-/-1 ,2,3-triazole (260 mg, 1 .61 mmol), Cs2C03 (2 N, 1 .34 mL, 2.68 mmol) in toluene (2 mL) and EtOH (6 mL) was added Pd(PPh3)4 (30.9 mg, 0.0268 mmol). The mixture was thoroughly degassed before heating under nitrogen at 80 C for 18 hr. TLC (EtOAc) indicated the reaction was completed. The mixture was concentrated under vacuum to dryness, and the residue purified by silica gel chromatography (petroleum ether/ EtOAc = 1/1 to 0/1) to give tert-butyl 4-({[2-amino-5-(1 -methyl-1 /-/-1 ,2, 3-triazol-4-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (I-60) (503 mg, 97%) as a white solid.

The synthetic route of 13273-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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. Recommanded Product: 288-36-8

Step 1) Synthesis of 5-methyl-2- (2H-1, 2, 3-triazol-2-yl) benzoic acid To a solution of N, N-dimethylformamide (30 mL) were added sequentially 2H-1, 2, 3-triazole (3.45 g, 50 mmol) , 2-iodo-5-methyl benzoic acid (5.24 g, 20 mmol) , cesium carbonate (11.72 g, 36 mmol) , trans-N, N’-dimethyl-1, 2-cyclohexanediamine (0.51 g, 3.6 mmol) and cuprous iodide (0.38 g, 2 mmol) . The reaction was heated to 100 ? under N2. After reaction for 4 hours, the reaction mixture was cooled to rt, diluted with water (60 mL) and extracted with ethyl acetate (200 mL × 2) . The aqueous layer was acidified to pH 1 to 2 with concentrated hydrochloric acid, and then extracted with ethyl acetate (200 mL × 2) . The combined organic layers were dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (DCM/methanol (v/v) =50/1) to give the title compound as a yellow solid (2.76 g, 68 %) .MS (ESI, neg. ion) m/z: 202.1 [M-H] -;1H NMR (CD3OD, 600 MHz) d (ppm) : 7.88 (s, 2H) , 7.66 (d, 1H) , 7.59 (d, J= 8.2 Hz, 1H) , 7.50-7.48 (dd, J = 8.1 Hz, 1.1 Hz, 1H) , 2.45 (s, 3H) ; and13C NMR (CD3OD, 151 MHz) d (ppm) : 169.8, 140.7, 137.5, 136.7, 133.5, 131.5, 129.3, 126.0, 21.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-36-8, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; ZHANG, Ji; (90 pag.)WO2017/88759; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 4928-87-4, A common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-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.

0.15 g (0.31 mmol) of intermediate 20 was dissolved in 30 ml CH2CI2, 0.1 g (0.52 mmol) of EDCI, 0.07 g (0.53 mmol)Eta0BetaTau,After stirring to dissolve, 0.03 g (0.27 mmol)1,2,4-triazole-3-carboxylic acid, stirred at room temperature12h, TLC detection. The reaction was carried out and the crude product was dried and purified by silica gel column chromatography (eluent: methanol / dichloromethane / aqueous ammonia = 50: 500: 1, ¥: ¥ ¥) to give a white solid. Example 16The target product, 0.1 g, yield 55.6%

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; 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

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, Quality Control of 2-(2H-1,2,3-Triazol-2-yl)benzoic acid

A solution of (R)-tert-butyl 5-methyl-l,4-diazepane-l-carboxylate Int A (2.50 g, 11.7 mmol) in DMF (50 mL) was treated with Int H (2.21 g, 11.7 mmol), HATU (4.47 g, 11.8 mmol), and DIEA (4.89 ml, 28.0 mmol). The reaction was stirred at room temperature overnight, then diluted with saturated, aqueous NH4CI. The solution was extracted with EtOAc (2x) and the organics were subsequently washed with brine, then with water, then with brine again, dried over MgS04, filtered, and concentrated. The crude material was purified by silica gel gradient chromatography (0-60% ethyl acetate in hexanes), providing 1-1 as an oil. LRMS m/z (M+H) 386.2 found, 386.2 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.; KUDUK, Scott, D.; REGER, Thomas, S.; SKUDLAREK, Jason, W.; (0 pag.)WO2016/85784; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 4928-87-4,Some common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, molecular formula is C3H3N3O2, 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 mixture of 8-azabicyclo[3.2. l]octan-3-yl)-3-(6-phenylpyridin-3-yl)-6,7,8,9- tetrahydropyrazolo[l,5-a]pyrido[3,2-e]pyrimidine (73 mg, 0.17 mmoL), lH-l,2,4-triazole-3- carboxylic acid (22.7 mg, 0.20 mmoL), EDC (64.0 mg, 0.33mmoL), HOBt (45.2 mg, 0.33 mmoL) and DIEA (173.9 mu, 1.00 mmoL) in DMF (2 mL) was stirred at room temperature for lh. Purification with prep-LC provided (3-(3-(6-phenylpyridin-3-yl)-6,7>8,9- tetrahydropyrazolo[l ,5-a]pyrido[3,2-e]pyrimidin-5-yl)-8-azabicyclo[3.2.1 ]octan-8-yl)(4H- lf2,4-triazol-3-yl)methanone: LCMS tR = 2.48 Min (10 min run, UV254nm). Mass calculated for, M+ 531.2, observed LC/MS m/z 532.0 (M+H).

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

Reference:
Patent; SCHERING CORPORATION; MENG, Zhaoyang; NAN, Yang; PATEL, Mehul; SIDDIQUI, M. Arshad; REDDY, Panduranga Adulla, P.; SUN, Binyuan; WO2012/27240; (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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 288-36-8

To a stirred solution of 1,2,3-triazole (2.0 g, 28.9 mmol) in THF (10 mL) was added NaH (1.065g, 43.1 mmol) portion wise at 0 C under inert atmosphere. After being stirred for 45 min at 0 C, 2-(trimethylsilyl)ethoxymethyl-Cl (SEM-C1; 7.6 mL, 43.1 mmol) was added to the reaction mixture. After completion of addition the reaction mixture was allowed to warm to RT and stirred for 12 h. The reaction mixture was quenched with water and extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to give crude compound. The crude material was purified by column chromatography eluting with 10% EtOAc/hexane to afford N-2- (trimethylsilyl)ethoxymethyl-l,2,3-triazole (3.5 g, 17.5 mmol, 61%) as a liquid. Mass: m/z 200 [M++l].

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; HOEKSTRA, William, J.; SCHOTZINGER, Robert, J.; RAFFERTY, Stephen, William; WO2012/64943; (2012); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics