1227594-89-9 | Pyridine-derivatives

The origin of a common compound about 1227594-89-9

According to the analysis of related databases, 1227594-89-9, the application of this compound in the production field has become more and more popular.

Synthetic Route of 1227594-89-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Step 8(f): 3-fluoro-1-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-4-(trifluoromethyl)pyridin-2(1 H)-one (8-8) To a solution of 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (8-5; 50 mg; 0.34 mmol) in dioxane 1.7 mL) was added K2CO3 (51 mg; 0.373 mmol) and the mixture was stirred for 5minutes. 5-(chloromethyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (8-4; 68 mg; 0.373 mmol) was then added, and the mixture was stirred for 2 hours at room temperature. The mixture was diluted with water, and extracted with CH2Cl2. The organic extracts were dried (MgSO4) and concentrated in vacuo. Purification by ISCO CombiFlash provided the title compound. 1H NMR (400 MHz, CDCl3): delta 10.14 (s, 1 H); 8.11 (d, J=5.2 Hz, 1 H); 7.18 (t, J=4.7 Hz, 1 H); 5.40 (s, 2 H); 3.41 (s, 3 H).

According to the analysis of related databases, 1227594-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Burch, Jason; Cote, Bernard; Nguyen, Natalie; Li, Chun Sing; St-Onge, Miguel; Gauvreau, Danny; US2011/245296; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Analyzing the synthesis route of 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1227594-89-9, 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one.

Electric Literature of 1227594-89-9, 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. 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, molecular formula is C6H3F4NO, The 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.

[00602] Step A: A solution of triphenylphosphine (1.34 g, 5.1 mmol) in THF (25 mL) was cooled to 0 C and treated with DIAD (1.0 mL, 5.12 mmol). The mixture was stirred for 15 min, then tert-butyl (3-bromo-1-((1r,4r)-4-hydroxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(ethyl)carbamate (1.5 g, 3.41 mmol) was added as a solid, followed by a solution of 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (1.24 g, 6.83 mmol) in THF (10 mL) over 5 min. The mixture was allowed to warm slowly to room temperature overnight. The mixture was partitioned between water (100 mL) and EtOAc (100 mL) and the aqueous layer was extracted with EtOAc (2 x 30 mL). The combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (10-40% EtOAc/hexanes) to afford tert-butyl (3-bromo-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(ethyl)carbamate (1.07 g, 52 % yield).

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Analyzing the synthesis route of 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one

Sources of common compounds: 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1227594-89-9, 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference of 1227594-89-9, 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. 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

[00640] tert-Butyl (1-((1r,4r)-4-hydroxycyclohexyl)-3-(1-methyl-1H-pyrazol-3-yl)-1H-pyrrolo[3,2-c]pyridin-6-yl)(methyl)carbamate (0.037 g, 0.087 mmol),3-fluoro-4-(trifluoromethyl)pyridin-2-ol (0.0472 g, 0.261 mmol), PPh3 (0.0684 g, 0.261 mmol) were dissolved in THF (1 mL) and then DIAD (0.0527 g, 0.261 mmol) was added and the reaction was stirred overnight. The reaction mixture was concentrated and then dissolved in DCM (1 mL) and 4M HCl in dioxane (2 mL) was added and stirred for 2 h. The reaction mixture was concentrated and purified by C18 preparative HPLC (5-95% ACN in water with 0.2% TFA) to afford 1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-N-methyl-3-(1-methyl-1H-pyrazol-3-yl)-1H-pyrrolo[3,2-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (12 mg, 19.3% yield). Mass spectrum (apci) m/z = 489.2 (M+H).1H NMR (CD3OD) delta 8.77 (s, 1H), 8.14 (d, 1H), 7.89 (s, 1H), 7.61 (s, 1H), 7.21 (m, 1H), 6.87 (s, 1H), 6.64 (s, 1H), 5.56 (s, 1H), 5.00 (m, 1H), 4.55 (m, 1H), 3.95 (s, 3H), 3.05 (s, 3H), 2.42-2.24 (m, 4H), 2.09-1.95 (m, 4H).

Application of 1227594-89-9

The synthetic route of 1227594-89-9 has been constantly updated, and we look forward to future research findings.

Related Products of 1227594-89-9 , The common heterocyclic compound, 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, molecular formula is C6H3F4NO, 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.

[00647] Step C: tert-butyl ethyl(1-((1r,4r)-4-hydroxycyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (50 mg, 0.12 mmol) was dissolved in THF (1 mL) and 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (63.5 mg, 0.35 mmol) and PPh3 (92 mg, 0.35 mmol) were added, followed by DIAD (0.069 mL, 0.35 mmol) and stirred overnight. The reaction mixture was concentrated and dissolved in DCM (1 mL) and 4M HCl in dioxane (2 mL) was added. After 2 h, the reaction was concentrated and purified by preparative HPLC (5 to 95% ACN in water with 0.2% TFA) to afford N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (17.2 mg, 20.5% yield). Mass spectrum (apci) m/z = 491.1 (M+H). 1H NMR (CD3OD) delta 9.05 (d, J = 0.8 Hz, 1H), 8.14 (m, 2H), 7.46 (d, J = 0.8 Hz, 1H), 7.20 (t, J = 4.7 Hz, 1H), 6.92 (s, 1H), 5.55 (m, 1H), 4.77 (m, 1H), 3.44 (q, J = 7.0 Hz, 2H), 2.51 (m, 2H), 2.36 (m, 2H), 2.05-1.95 (m, 4H), 1.38 (t, J = 7.0 Hz, 3H).

The synthetic route of 1227594-89-9 has been constantly updated, and we look forward to future research findings.

Simple exploration of 1227594-89-9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227594-89-9, its application will become more common.

Application of 1227594-89-9 ,Some common heterocyclic compound, 1227594-89-9, molecular formula is C6H3F4NO, 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.

[00542] Step C: tert-butyl ethyl(1-((1r,4r)-4-hydroxycyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (30 mg, 0.07 mmol) was dissolved in THF (0.5 mL). 6-hydroxy-2-methylpyridazin-3(2H)-one (26 mg, 0.21 mmol) and PPh3 (55 mg, 0.21 mmol) were added, followed by DIAD (0.041 mL, 0.21 mmol). The reaction mixture was stirred overnight and then concentrated. The residue was dissolved in DCM (1 mL) and 4N HCl in dioxane (1 mL) was added and stirred for 2 h. The reaction mixture was concentrated and the residue purified on C-18 silica column (5 to 95% ACN in water with 0.1% TFA) to afford N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (17.2 mg, 20% yield). Mass spectrum (apci) m/z = 436.2 (M+H).1H NMR (CD3OD) delta 9.05 (s, 1H), 8.15 (s, 1H), 7.47 (s, 1H), 7.28 (d, J = 9.6 Hz, 1H), 7.00 (d, J = 9.6 Hz, 1H), 6.97 (s, 1H), 5.16 (m, 1H), 4.75 (m, 1H), 3.65 (s, 3H), 3.45 (q, J = 7.2 Hz, 2H), 2.50-2.31 (m, 4H), 1.99-1.86 (m, 4H), 1.38 (t, J = 7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227594-89-9, its application will become more common.

Analyzing the synthesis route of 1227594-89-9

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. 1227594-89-9, 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Electric Literature of 1227594-89-9 ,Some common heterocyclic compound, 1227594-89-9, molecular formula is C6H3F4NO, 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.

[00643] Step C: (1r,4r)-4-(6-(ethylamino)-3-(2-methyloxazol-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexan-1-ol (0.0101 g, 0.0296 mmol), 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (0.0161 g, 0.0887 mmol), PPh3 (0.0233 g, 0.0887 mmol) were dissolved in THF (0.5 mL) and then DIAD (0.0179 g, 0.0887 mmol) was added and stirred overnight and then concentrated. The residue was purified over preparative HPLC (5-95% ACN in water with 0.2% TFA) and concentrated to afford N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(2-methyloxazol-5-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (5.6 mg, 25.8 % yield). Mass spectrum (apci) m/z = 505.2 (M+H).1H NMR (CD3OD) delta 8.91 (s, 1H), 8.13 (d, 1H), 7.70 (s, 1H), 7.20 (m, 1H), 6.82 (s, 1H), 5.53 (s, 1H), 4.99 (m, 1H), 4.70 (m, 1H), 3.42 (q, J = 7.0 Hz, 2H), 2.61 (s, 3H), 2.53-2.30 (m, 4H), 1.96 (m, 4H), 1.36 (t, J = 7.0 Hz, 3H).

The important role of 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one

With the rapid development of chemical substances, we look forward to future research findings about 1227594-89-9.

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. 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, molecular formula is C6H3F4NO, The 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. Application In Synthesis of 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one

A mixture of 2 (100 mg, 93.1% purity, 0.49 mmol), pyridone (1 17 mg, 97.6% purity, 0.49 mmol) and K2CO3 (82 mg, 0.59 mmol) in DMF (0.5 ml) was aged with stirring at ambient temperature for 3h. After the reaction was completed, the batch was taken on to the next step without further work up or isolation.

With the rapid development of chemical substances, we look forward to future research findings about 1227594-89-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ITOH, Tetsuji; JEON, Ingyu; MANGION, Ian; QIAN, Gang; SHERRY, Benjamin, D.; GAUTHIER, Donald, R.; CAO, Yang; WO2014/89140; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The important role of 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one

With the rapid development of chemical substances, we look forward to future research findings about 1227594-89-9.

Simple exploration of 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one

Electric Literature of 1227594-89-9, Adding some certain compound to certain chemical reactions, such as: 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one,molecular formula is C6H3F4NO, 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 1227594-89-9.

[00778] Step C: A solution of triphenylphosphine (39 mg, 0.149 mmol) in THF (1 mL) at room temperature was treated with DIAD (29 muL, 0.149 mmol). The mixture was stirred for 10 min and then tert-butyl (3-(1-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-1-((1r,4S)-4-hydroxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (50.9 mg, 0.099 mmol) was added in THF (1 mL), followed by 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (36 mg, 0.199 mmol). The mixture stirred overnight and partitioned between water (15 mL) and EtOAc (10 mL). The aqueous layer was extracted with EtOAc (2 x 10 mL). The combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified over silca gel (20-70% EtOAc in hexanes) to afford tert-butyl (3-(1-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-1-((1s,4R)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (77.7 mg, 115% yield).