Category: 16681-70-2

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. HPLC of Formula: C3H3N3O2

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 dimethylcarbamoylmethyl ester (49 mg, 120 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 (51 mg; purity 95%). MS m/z [M+H]+ calc’d for C26H31N5O5, 494.23. found 494.2.

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, INC.; US2012/213806; (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. 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., Quality Control of 1H-[1,2,3]Triazole-4-carboxylic acid

[0610] 3H-1,2,3-triazole-5-carboxylic acid (1.1 mg, 10.0f.tmol) was combined with HATU (3.0 mg, 7.8 flillOI) in DMF(0.5 mL) and stirred for 10 minutes; DIPEA (1.0 eq.) wasadded and the mixture was stirred for 1 minute. Compound 2(4.7 mg, 11 f.tmol) was dissolved in DMF (1 mL) and DIPEA(5.8 f.LL, 33 mmol) was added, followed by addition of theactivated acid solution. The mixture was stirred for 30 minutesto yield crude Compound 3.

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 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

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., name: 1H-[1,2,3]Triazole-4-carboxylic acid

lH-l,2,3-triazole-5-carboxylic acid (1.1 mg, 10.0 muiotaetaomicron) was combined with HATU (3.0 mg, 7.8 muiotaetaomicron) in DMF (0.5 mL) and stirred for 10 minutes; DIPEA (1 eq.) was added and the mixture was stirred for 1 minute. Compound 2 (5.0 mg, 11 muiotaetaomicron) was dissolved in DMF (1 mL) and DIPEA (5.8 mu^, 33 muiotaetaomicron) was added, followed by addition of the activated acid solution. yield Compound 3.

According to the analysis of related databases, 16681-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FLEURY, Melissa; BEAUSOLIEL, Anne-Marie; HUGHES, Adam D.; LONG, Daniel D.; WILTON, Donna A.A.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route 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.

O. (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid isobutyl ester (R4=H; R7=-CH2CH(CH3)2) (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 2-methyl-propan-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 (36 mg; purity 95%). MS m/z [M+H]+ calc’d for C26H32N4O4, 465.24. found 465.4.

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

Reference 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 2-morpholin-4-yl-2-oxo-ethyl ester (54 mg, 120 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 (35 mg; purity 95%). MS m/z [M+H]+ calc’d for C28H33N5O6, 536.24. found 536.2.

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

Application 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.

General procedure: To a stirred solution of 680 mg (1 .78 mmol) (3aR,4S,7R,7aS)-8-{[2-(trifluoro-methyl)phenyl]sulfonyl}octahydro-1H-4,7-epiminoisoindole hydrochloride (1 :1 ) (Intermediate 1) in 10 mL DMF were added 301 mg 1 H-1 ,2,3-triazole-4-carboxylic acid (2.66 mmol, 1 .5 eq), 590 mu 4-methylmorpholine (5.3 mmol, 3 eq) and 1 .01 g HATU (2.66 mmol, 1 .5 eq). After stirring for 16 h at RT, the solution was subjected to preparative HPLC to yield 473 mg (60 %) 1 H-1,2,3-triazol-5-yl[(3aR,4S,7R,7aS)-8-{[2-(trifluoromethyl)phenyl]sulfonyl}octahydro-2H-4,7-epiminoisoindol-2-yl]methanone. LC-MS (Method A1 ): Rt = 0.98 min; MS (ESIpos): m/z = 442 [M+H]+ 1 H NMR (400 MHz, DMSO-d6): delta [ppm] = 1 .40 – 1 .65 (m, 4 H) 2.80 – 3.01 (m, 2 H) 3.1 1 (dd, 1 H) 3.44 (dd, 1 H) 3.93 – 4.10 (m, 1 H) 4.23 (br s, 2 H) 4.39 (br s, 1 H) 7.83 – 7.96 (m, 2 H) 7.98 – 8.07 (m, 1 H) 8.23 – 8.29 (m, 1 H) 8.34 (br s, 1 H) 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 0.851 (1 .86), 1 .154 (4.18), 1 .171 (8.33), 1 .189 (4.15), 1 .232 (5.06), 1 .352 (1 .25), 1 .476 (3.05), 1 .498 (3.54), 1.545 (3.32), 1 .568 (2.64), 1.907 (4.52), 1 .987 (16.00), 2.006 (1.15), 2.332 (1 .00), 2.518 (4.20), 2.523 (3.25), 2.673 (1 .07), 2.686 (1 .44), 2.727 (2.10), 2.869 (1.54), 2.888 (4.37), 2.900 (1.51), 2.919 (1.42), 2.936 (1.81), 2.950 (1.59), 3.079 (1.93), 3.098 (1.95), 3.112 (2.32), 3.133 (1.78), 3.418 (1.78), 3.437 (1.88), 3.450 (2.13), 3.469 (1.64), 3.987 (3.57), 3.999 (1.42), 4.017 (5.50), 4.021 (3.40), 4.034 (3.49), 4.052 (1.15), 4.229 (4.91), 7.884 (3.44), 7.886 (3.44), 7.894 (3.96), 7.901 (8.45), 7.905 (3.69), 7.913 (4.08), 7.918 (4.32), 7.932 (1.44), 7.936 (1.00), 8.004 (4.86), 8.010 (4.74), 8.022 (2.59), 8.027 (3.37), 8.256 (4.32), 8.261 (3.10), 8.274 (4.15), 8.279 (3.47), 8.342 (1.47).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SIEBENEICHER, Holger; STEUBER, Holger; TER LAAK, Antonius; NUBBEMEYER, Reinhard; ROTTMANN, Antje; IRLBACHER, Horst; BADER, Benjamin; PETERS, Michaele; WAGENFELD, Andrea; (110 pag.)WO2018/114677; (2018); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. Computed Properties of C3H3N3O2

lH-l,2,3-triazole-5-carboxylic acid (3.1 mg, 27 muiotaetaomicron) was combined with HATU (10.4 mg, 27 muiotaetaomicron) in DMF (0.5 mL), and stirred for 10 minutes. DIPEA (4.8 mu, 27 Mmol) was added and the resulting mixture was stirred for 1 minute. Compound 2 (12 mg 27 muiotaetaomicron) dissolved in DMF (1 mL) was combined with added DIPEA (14.4 mu, 82 muiotaetaomicron) followed by addition of the activated acid solution. The resulting mixture was stirred for 30 minutes then purified by reverse phase chromatography (0-100% EtOAc/hexanes to yield Compound 3 (10

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid 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.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference 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.

[0742] To a solution of Compound 1 (15.9 mg, 30 f.tmol) indioxane (0.3 mL) was added HCI (149 f.LL, 598 fllllOI). Theresulting solution was stirred at room temperature for 2 hours,and then concentrated in vacuo. In a separate flask, a solutionof 3H-[1,2,3]triazole-4-carboxylic acid (4.1 mg, 36 f.tmol)and HATU (14 mg, 36 f.tmol) in DMF (0.3 mL) was stirred atroom temperature for 30 minutes. After this time, a solution ofthe crude amine in DMF (0.3 mL) was added, followed byDIPEA (16 f.LL, 90 f.tmol). The resulting solution was stirredfor 1 hour at room temperature then concentrated in vacuowhen the reaction was deemed complete by LCMS to yieldCompound 2 (16 mg), which was used without further purification.

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; 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

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic 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 16681-70-2, Safety of 1H-[1,2,3]Triazole-4-carboxylic acid

Example 20 3-{(R)-3-(5?-Chloro-2?-fluorobiphenyl-4-yl)-2-[(3H-[1,2,3]triazole-4-carbonyl)amino]propyl}tetrahydrofuran-3-carboxylic Acid (isomers a and b) [0453] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]tetrahydrofuran-3-carboxylic acid (isomer a; 10 mg, 24 mumol, 1.0 eq.) and DIPEA (20 muL, 100 mumol, 4.0 eq.) were dissolved in DMF (100 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 88 mumol, 3.7 eq.), HATU (15 mg, 39 mumol, 1.6 eq.), and DIPEA (40 muL, 200 mumol, 8.0 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for ten minutes, then both solutions were combined and stirred at room temperature and when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture; the organics were then separated, concentrated and purified by preparative HPLC to yield the title compound (isomer a; 7.8 mg). LCMS (ESI): calc. C23H22ClFN4O4=472; obs. M+H=473.0. Retention time: 4.73 min. [0455] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]tetrahydrofuran-3-carboxylic acid (isomer b; 10 mg, 24 mumol, 1.0 eq.) and DIPEA (20 muL, 100 mumol, 4.0 eq.) were dissolved in DMF (100 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 88 mumol, 3.7 eq.), HATU (15 mg, 39 mumol, 1.6 eq.), and DIPEA (40 muL, 200 mumol, 8.0 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for ten minutes, then both solutions were combined and stirred at room temperature. When the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture; the organics were then separated, concentrated and purified by preparative HPLC to yield the title compound (isomer b; 2.9 mg). LCMS (ESI): calc. C23H22ClFN4O4=472; obs. M+H=472.9. Retention time: 4.77 min. [0456] 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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-[1,2,3]Triazole-4-carboxylic acid, and friends who are interested can also refer to it.

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

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

1,2,3-Triazole-4-carboxylic acid (45.2 mg, 400 mumol), DIPEA (209 muL, 1.2 mmol) and HCTU (165 mg, 400 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 1-cyclohexyloxycarbonyloxy-ethyl ester (193 mg, 400 mumol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The products were purified and separated by preparative HPLC, then lyophilized to yield to yield compound ZC (20 mg; purity 95%), MS m/z [M+H]+ calc’d for C31H38N4O2, 579.27. found 579.6, and compound ZD (15 mg; purity 95%), MS m/z [M+H]+ calc’d for C31H38N4O2, 579.27. found 579.6.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-[1,2,3]Triazole-4-carboxylic acid, and friends who are interested can also refer to it.

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