Triazoles

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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Recommanded Product: 16681-65-5

To a flask containing 1-methyl-1H-1,2,3-triazole (160 mg, 1.93 mmol) was added THF (12 mL) and the colorless solution was cooled to -43 C. using a CH3CN-CO2 bath. Then, n-BuLi, (2.5 M in hexanes, 0.72 mL, 1.8 mmol) was added which afforded an opaque white suspension. The suspension was stirred at -40 C. for 20 minutes, then a homogeneous solution of (2-chloro-4-methoxy-3-(2,2,2-trifluoroethyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (350 mg, 0.88 mmol, Intermediate 59: step c) in 5 mL THF, was introduced at -40 C. The reaction mixture was allowed to warm gradually to 0 C. over 25 minutes, then quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (3*35 mL). The combined organics were washed with brine, dried over Na2SO4 and MgSO4, filtered and concentrated to give a brown solid. Chromatography on silica gel (3% MeOH-DCM increasing to 10% MeOH) provided the title compound as a tan amorphous solid. 1H NMR (500 MHz, CD3OD) delta ppm 8.22 (d, J=1.8 Hz, 1H), 8.05 (d, J=8.9 Hz, 1H), 7.70 (dd, J=8.9, 2.0 Hz, 1H), 7.48 (s, 1H), 6.91 (s, 1H), 4.09 (s, 3H), 4.03-3.89 (m, 5H), 3.69 (s, 3H), 2.66 (s, 3H). MS (ESI): mass calcd. for C21H20ClF3N6O2, 480.1. found, 481.1 (M+H)+.

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; 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

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. 288-88-0, name is 1H-1,2,4-Triazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1H-1,2,4-Triazole

Example 91 Preparation of 4-(1H-1,2,4-triazol-1-yl)benzaldehyde (DI5) To a stirring solution of 4-fluorobenzaldehyde (10.0 g, 80.6 mmol) in DMF (150 mL) were added K2CO3 (13.3 g, 96.7 mmol) and 1,2,4-triazole (6.67 g, 96.7 mmol) and the resultant reaction mixture was stirred at 120 C. for 6 h. After completion of reaction (by TLC), the reaction mixture was diluted with water and extracted with EtOAc (3*100 mL). The combined EtOAc layer was washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a solid (9.0 g, 65%): mp 145-149 C.: 1H NMR (400 MHz, CDCl3) delta 10.08 (s, 1H), 8.70 (s, 1H), 8.16 (s, 1H), 8.06 (d, J=8.0 Hz, 2H), 7.92 (d, J=8.0 Hz, 2H); ESIMS m/z 173.9 ([M+H]+).

According to the analysis of related databases, 288-88-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171314; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-70-2, These common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-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.

[0776] 38-1,2,3-triazole-5-carboxylic acid (3.0 mg, 27f.tmol) was combined with HATU (1 0.1 mg, 27 flillOl) in DMF(0.5 mL); DIPEA ( 4.7 f.LL, 27 f.tmol) was added and the mixturewas stirred for 5 minutes. Compound 2 (12 mg, 27 f.tmol)was dissolved in DMF (0.5 mL) and DIPEA (13.9 f.LL, 80f.tmol) and combined with the activated acid solution. Themixture was stirred for 10 minutes, at which time LCMSindicated the mass of the desired compound. The solvent wasremoved under reduced pressure and the residue was purifiedby reverse phase chromatography to yield Compound b (8mg) as a TFA salt. MS m/z [M+Ht calc’d forC22H33ClFN50 4 , 546.22. found 546.

Statistics shows that 1H-[1,2,3]Triazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 16681-70-2.

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

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 7411-23-6 as follows. SDS of cas: 7411-23-6

A Compound WX122-1 (4 g) was dissolved in DMF (100 ml) and the resulting solution was cooled down to0C. NaH (846.3mg) was added in batch. Gas was generated during the process, and after 0.5 hour, MeI (2.6 grams)was added dropwise into the reaction solution which was slowly heated to 25C namely room temperature and stirredfor 12 hours. The reaction solution was poured into a saturated ammonium chloride solution (300ml), and extracted withethyl acetate (50ml33), and the organic phase was washed with a saturated sodium chloride solution (100ml). Theorganic phases were mixed and dried with anhydrous sodium sulfate, filtered, and concentrated under the reducedpressure. This compound was used directly in the next step and did not require purification. ESI m/z: [M+H]+= 242.

According to the analysis of related databases, 7411-23-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Danhong Pharmaceutical Co., Ltd.; LUO, Zhi; LI, Xiaolin; YANG, Yaxun; YANG, Lele; LI, Peng; HE, Haiying; LI, Jian; CHEN, Shuhui; (155 pag.)EP3626699; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 13423-60-4, The chemical industry reduces the impact on the environment during synthesis 13423-60-4, name is 1-Phenyl-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life.

EXAMPLE 110 1-phenyl-4-(hex-1-yl)triazolium bromide 0.300 g (0.002 mol) 1-phenyltriazole 1 and 0.842 ml (0.990 g, 0.006 mol) 1-bromohexane 2 were dissolved in a pressure tube in 5 ml THF. The reaction mixture was stirred 3 d at 110 C. On account of a broken seal the solvent had evaporated was after that time. 1-bromohexane 2 and THF were added again and stirring was continued. The reaction mixture was cooled down and the same volume petroleum ether added. The precipitated solid is filtered off, washed with petroleum ether, and dried in HV. While the solvent had already evaporated the reaction seemed to run better, because this experiment provided considerably higher yields than all THF experiments. M 310.24 C14H20N3Br Yield: 0.4601 g (74%) 1H-NMR DM-107 (300 MHz/DMSO): delta (ppm)=0.88 (t, 3H, 12-H); 1.33 (m, 6H, 9/10/11H); 1.94 (q, 2H, 8-H); 4.31 (t, 2H, 7-H); 7.70 (m, 3H, 5/5’/6H); 7.96 (d, 2H, 4/4′-H); 9.51 (s, 1H, 1-H); 11.00 (s, 1H, 2-H) 13C-NMR DM-107.w (300 MHz/DMSO):

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, 1-Phenyl-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TECHNISCHE UNIVERSITAET DRESDEN; US2011/105761; (2011); 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, 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. SDS of cas: 252742-72-6

1-200: N2-(3-Aminosulfonyl-4-fluorophenyl)-5-fluoro-N4-[4-(254-dihydro-3-oxo-l,2,4- triazol-5-yl)methyleneoxyphenyI]-2,4-pyrimidinediamine (76); [0719] To a solution of 5-chloromethyl-2,4-dihydro-l ,2,4-triazol-3-one (35 mg, 0.26 mmol) in 2-butanone, were added N2-(3-aminosulfonyl-4-fluorophenyl)-5-fluoro-N4-(4- hydroxyphenyl)-2,4-pyrimidmediamme (100 mg, 0.25 mmol) and potassium carbonate (35 mg, 0.25 mmol). The resulting mixture was micro waved at 140 0C for 5 hours, and then additional of 5-chloromethyl-2,4-dihydro-l,2,4-triazol-3-one was added as needed The reaction solvent was removed under a reduced pressure, and the residual was purified by column chromatography (silica gel, dichloromethane: methanol 8:2 v/v) to give 25 mg of N2- (3-aminosulfonyl-4-fluorophenyl)-5-fluoro-N4-[4-(2,4-dihydro-3-oxo-l,2,4-triazol-5- yl)methoxyphenyl]-2,4-pyrimidinediamine (76) as a light yellow solid. 1H NMR (D2O): delta 7.90-7.89 (d, J= 3 Hz, 1H), 7.60-7.58 (d, J= 6 Hz, 1H), 7.34 (bs, 2H), 7.24-7.18 (m, 2H), 7.05-7.02 (d, J= 9.0 Hz, 2H), 6.65-6.62 (d, J= 9.0 Hz, 2H), 5.11 (br s, 2H); LCMS (m/z): 491.05 (MH+).

The synthetic route of 252742-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2006/133426; (2006); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-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. name: 1H-[1,2,3]Triazole-4-carboxylic acid

(R)-4-Amino-5-(5?-chloro-2?-fluorobiphenyl-4-yl)-2-ethyl-2-hydroxymethylpentanoic acid (isomer a; 85 mg, 190 mumol, 1.0 eq.) and DIPEA (250 muL, 1.4 mmol, 7.5 eq.) were dissolved in DMF (800 muL). 1H-1,2,3-triazole-4-carboxylic acid (32 mg, 290 mumol, 1.5 eq.), HATU (70 mg, 184 mumol, 1.0 eq.), and DIPEA (100 muL, 572 mumol, 7.5 eq.) were dissolved in DMF (500 muL) and stirred at room temperature for 15 minutes. The solutions were then combined and the resulting mixture stirred at room temperature for 20 minutes and when the reaction was complete (as determined by LC/MS analysis), the mixture was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer a; 21.9 mg). LCMS (ESI): calc. C23H24ClFN4O4=474; obs. M+H=475.1. Retention time: 4.75 min. [0432] (R)-4-Amino-5-(5?-chloro-2?-fluorobiphenyl-4-yl)-2-ethyl-2-hydroxymethylpentanoic acid (isomer b; 85 mg, 190 mumol, 1.0 eq.) and DIPEA (250 muL, 1430 mumol, 7.5 eq.) were dissolved in DMF (800 muL). 1H-1,2,3-triazole-4-carboxylic acid (32 mg, 290 mumol, 1.5 eq.), HATU (70 mg, 184 mumol, 1.0 eq.), and DIPEA (100 muL, 572 mumol, 7.5 eq.) were dissolved in DMF (500 muL) and stirred at room temperature for 15 minutes. The solutions were then combined and the resulting mixture stirred at room temperature for 20 minutes and when the reaction was complete (as determined by LC/MS analysis), the mixture was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer b; 37.8 mg). LCMS (ESI): calc. C23H24ClFN4O4=474; obs. M+H=475.0. Retention time: 4.72 min. [0433] LC/MS Method: flow rate: 1.5 mL/min; Buffer A: 0.1% TFA/H2O; Buffer B 0.1% TFA/MeCN; gradient elution from 5%-100% B over 9.6 min, then 100% B for 1.0 minute, detection at 254 nm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-70-2, its application will become more common.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/209352; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-70-2, These common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-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.

H. (2S,4S)-5-Biphenyl-4-yl-2-hydroxymethyl-4-[(3H-[1,2,3]-triazole-4-carbonyl)-amino]-pentanoic acid 2-methanesulfonyl-ethyl ester (R7=-(CH2)2SO2CH3) (2S,4S)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-pentanoic acid (100 mg, 250 mumol, 1.0 eq.), HOBt (0.1 g, 750 mumol, 3.0 eq.), and EDCI (130 muL, 3.0 eq.) were dissolved in DCM (2 mL). After stirring for 10 minutes, 2-(methylsulfonyl)-ethanol (250 mg, 2.0 mmol, 8.0 eq.) and 4-methylmorpholine (110 muL, 4.0 eq.) were added. The resulting mixture was stirred at room temperature for 1.5 hours. The reaction was quenched with water. The DCM layer was separated, concentrated, and the product purified by flash chromatography (70-100% EtOAc/hexanes over 15 minutes). The clean fractions were combined and concentrated. MeCN (2.5 mL) and 4 M of HCl in dioxane (250 muL, 4.0 eq.) were added and the resulting mixture was stirred at room temperature for 1 hour. 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 (28.3 mg, 250 mumol, 1.0 eq.) and HATU (95.2 mg, 250 mumol, 1.0 eq.) were dissolved in DMF (2.0 mL) and the resulting solution was stirred for 5 minutes, followed by the addition of DIPEA (131 muL) and the intermediate HCl salt. After 5 minutes, the reaction was quenched with water and the product purified by preparative HPLC to yield the title compound (64 mg; purity 95%). MS m/z [M+H]+ calc’d for C24H28N4O6S, 501.17. found 501.4.

Statistics shows that 1H-[1,2,3]Triazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 16681-70-2.

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

Adding a certain compound to certain chemical reactions, such as: 202931-88-2, name is 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde, 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 202931-88-2, Safety of 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde

General procedure: A solution of 19 (300 mg, 0.70 mmol) in tetrahydrofuran (3 mL) was slowly added to a solution of lithium diisopropylamide (LDA) in heptane/tetrahydrofuran/ethylbenzene (2 M, 0.38 mL, 0.76 mmol) at 78oC, and the resultant solution was stirred at -78oC for 30 minutes. Chlorotitanium triisopropoxide (1 M, 2.8 mL) was then added slowly, and the resulting mixture was stirred at 40oC for 1 hour. The reaction was cooled to -78oC, and propionaldehyde (49 mg, 0.84 mmol) was added slowly. This mixture was then warmed to 40oC, and stirred at 40oC for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (1 mL), diluted with 10 mL of tetrahydrofuran, and treated with Celite for 1 hour. The resultant slurry was filtered and concentrated. The resultant residue was purified by silica gel chromatography (gradient: 95:5 hexanes:ethyl acetate to 65:35 hexanes:ethyl acetate) to provide 20 as a white solid. Yield: 230 mg, 68%.

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, 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Warmus, Joseph S.; Quinn, Cheryl L.; Taylor, Clarke; Murphy, Sean T.; Johnson, Timothy A.; Limberakis, Chris; Ortwine, Daniel; Bronstein, Joel; Pagano, Paul; Knafels, John D.; Lightle, Sandra; Mochalkin, Igor; Brideau, Roger; Podoll, Terry; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2536 – 2543;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 31250-99-4, 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. 31250-99-4, name is 1-Trityl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 6 This Example illustrates the preparation of 1-trityl-3-bromo-1,2,4-triazole. A stirred solution of 1-trityl-1,2,4-triazole (15.55 g, prepared as described in Example 1) and N,N,N’,N’-tetramethylethylenediamine (5.8 g) in dry tetrahydrofuran (500 ml) was cooled to -70 C. under nitrogen and treated dropwise with n-butyllithium (37.5 ml, 1.6M in hexane). The deep-red solution was stirred at -70 C. for twenty minutes, then treated dropwise with a solution of bromine (10.4 g) in dry tetrahydrofuran (10 ml). The now brownish-yellow solution was allowed to warm to -20 C., quenched with 0.1M sodium thiosulphate solution (150 ml), and extracted with dichloromethane (500 ml). The organic layer was washed with water (4*100 ml), dried and evaporated. The residue was chromatographed on silica, using dichloromethane-ether (25:2) as eluant, to give 1-trityl-5-bromo-1,2,4-triazole (7.86 g, m.p. 239-241 C.). NMR (CDCl3):delta7.1-7.3(15H,m), 7.95(1H,s).

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

Reference:
Patent; Zeneca Limited; US5393732; (1995); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics