Category: Triazoles

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

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

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

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. 815588-93-3, name is 1-Methyl-1H-1,2,4-triazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 815588-93-3

A mixture of 1 -methyl-1 H-1 , 2, 4-triazole-5-carboxylic acid (7.0 g, 55.1 mmol) in SOCI2 (20 mL) was heated to 70 ¡ãC for 2 h. The mixture was concentrated to dryness. The residue was dissolved in NHa/MeOH (7M, 40 mL) and stirred at rt overnight. The precipitated solid was filtered off, extracted with Et20 and dried under reduced pressure to give the title compound.

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 815588-93-3.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; DEUSCHLE, UIrich; STEENECK, Christoph; ALBERS, Michael; HOFFMANN, Thomas; (62 pag.)WO2018/153893; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 6523-49-5, 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. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

Example B3; Preparation of (compound 3); Reaction under Argon flow. Dry DMSO (0.5 ml) was added to a mixture of intermediate 5 (0.000428 mol) and 4-(lH-l,2,4-triazol-l-yl)-benzenamine (0.000642 mol). The reaction mixture was stirred for 6 hours at 100 C on an oil-bath (no result; only starting material). Cs2CO3 (0.227 g, 1.5 equiv) was added and the reaction mixture was stirred for 3 hours at 100 0C. This mixture was extracted with a mixture of EtOAc/NaHCO3/H2O/NaCl. The extract’s solvent was evaporated. The residue (0.172 g) was washed with diethyl ether, a mixture of diethyl ether/DCM, then purified by EPO column chromatography over silica gel (eluent: toluene/2-propanone gradient). The product fractions were collected and the solvent was evaporated, yielding 0.024 g of compound 3, melting point 222.5-224 0C.

The chemical industry reduces the impact on the environment during synthesis 4-(1,2,4-Triazol-1-yl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/74984; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3641-08-5, name is 2H-1,2,4-Triazole-3-carboxamide, molecular formula is C3H4N4O, 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. category: Triazoles

EXAMPLE 4 Preparation of 1(and 2 and 4)-Benzoyl-s-triazole-3-carboxamide To a cooled, stirred mixture of 3 g. of 1,2,4-triazole-3-carboxamide and 4 g. of benzoyl chloride in 125 ml. of anhydrous diethyl ether is added rapidly 2.75 g. of triethylamine. The cooling bath is removed and the mixture is stirred at room temperature for 18 hours. The heterogeneous mixture is filtered and washed successively with diethyl ether, cold water and then diethyl ether and dried in vacuo for 4 hours yielding 4 g. of colorless solid. This solid is extracted with hot, dry acetonitrile and cooled yielding a solid product which is collected, washed with acetonitrile and dried in vacuo, yielding 1 g. of product, m.p. 174-178 C. (dec.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3641-08-5, its application will become more common.

Reference:
Patent; American Cyanamid Company; US4006159; (1977); A;,
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. 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, A new synthetic method of this compound is introduced below., COA of Formula: C9H7N3O

Weigh 1.73 g (10 mmol) of 1,2,4-triazole benzaldehyde, 4.15 g (12 mmol) of fluorescein hydrazide, dissolved in50 mL of hot ethanol, and added to a 100 mL three-pack equipped with a thermometer and a stirring device. In the flask.To the above mixed solution,0.63 ml (10 mmol) of glacial acetic acidwasadded, and the mixture was refluxed under stirring at 80 C for 5 h, cooled to room temperature, and a white solid was precipitated,washed with cold ethanol, and dried under vacuum at 50 C for 8 h to obtain the final product compound. (Triazolyl benzaldehyde to fluorescein hydrazide Schiff base).Yield: 84%.

The synthetic route of 27996-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qilu University of Technology; Duan Hongdong; Zhong Wenxia; (12 pag.)CN109867683; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-36-8, 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.

Example 120: Preparation of 4,5-dibromo-lH-?,2,31triazoleRr Br. BrN^ NH *” ‘ V NVNH To a solution of IH-[1, 2,3]triazole (1.26 ml, 21.7 mmol) in water (10 ml) at 5tfC, was added bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at 5CPC for 1.5 hours. The white solid (2.375 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (1.83 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (375 mg) was isolated via filtration and washed with water (5ml). The white solids were combined and dried to give 4,5-dibromo- IH-[1, 2,3]- triazole (4.92 g, 93% yield). M.p. 194.7C.

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

Reference:
Patent; SYNGENTA LIMITED; WO2007/96576; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4928-88-5,Some common heterocyclic compound, 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, molecular formula is C4H5N3O2, 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 3A Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate (20) A mixture of methyl 1,2,4-triazole-3-carboxylate (0.64 g, 5 mmol), 1,2,3,5-tetra-O-acetyl-beta-L-ribofuranose (2) (1.5 g, 4.72 mmol) and bis(p-nitrophenyl)-phosphate (20 mg) were placed in a pear shaped flask and placed in a preheated oil bath at (160-165¡ã C.). The flask was connected to a water aspirator and kept at 160-165¡ã C. (oil bath temperature) under reduced pressure with stirring for 25 min. The reaction mixture was removed, cooled and diluted with EtOAc (150 mL) and sat. NaHCO3 (100 mL). The product was extracted in EtOAc. The organic extract was washed with water (100 mL) and brine (50 mL), dried and evaporated to dryness. The residue that obtained was purified by flash column of silica gel using CHCl3 –>EtOAc as the eluent. The pure fractions were collected and evaporated to dryness to give 1.2 g (66percent) of pure product: 1 H NMR (CDCl3) delta 2.10 (3s, 9H, 3 COCH3), 3.98 (s, 3H, OCH3), 4.22 (m, 1H), 4.46 (m, 2H), 5.54 (t, 1H), 5.76 (m, 1H), 6.04 (d, 1H, C1′,), and 8.38 (s, 1H, C3 H). Anal. Calc. for C15 H19 N3 O9 (385.22): C, 46.75; H, 4.97; N,10.91. Found: C, 46.82; H, 4.57; N=10.71.

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

Reference:
Patent; ICN Pharmaceuticals, Inc.; US6130326; (2000); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, 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. 288-36-8 name is 1H-1,2,3-Triazole, 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.

Intermediate 1 : 5-Fluoro-2-[1 ,2,3]triazol-2-yl-benzoic acid.5-Fluoro-2-[1 ,2,3]triazol-2-yl-benzoic acid. To a solution of 5-fluoro-2- iodo-benzoic acid (3.86 g, 14.65 mmol), 2H-[1 ,2,3]triazole (2.5 g, 36.2 mmol), Cs2C03 (8.62 g, 24.5 mmol), frans-N,N’-dimethyl-cyclohexane-1 ,2-diamine (0.4 mL), Cul (244 mg) and DMF (13 mL) were added to a microwave ready vessel and heated to 100 C for 10 min. The mixture was cooled, diluted with water, and extracted with EtOAc. The aqueous layer was acidified and extracted with EtOAc. The organic layer was dried over Na2S04 and concentrated.Chromatography (DCM to 10% MeOH/1 % HOAc/DCM) gave the product as a white powder (2.14 g, 71 %). 1H NMR (400 MHz, CD3OD): 7.91 (s, 2H), 7.76 (dd, J = 8.9, 4.8 Hz, 1 H), 7.59 (dd, J = 8.5, 2.9 Hz, 1 H), 7.49 – 7.42 (m, 1 H).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics