Tag: M.W=400-500

Synthetic Route of 914942-88-4 ,Some common heterocyclic compound, 914942-88-4, molecular formula is C13H18IN5O2, 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.

Copper iodide (5.0mg, 0.025mmol) and dichlorobis(triphenylphosphine) palladium (4.0mg, 0.050mmol) were each added in one portion to a mixture of Al.12 (lOOmg, 0.25mmol), phenylacetylene (28mg, 0.28mmol) and triethylamine (0.11ml, 0.75mmol) in dichloromethane (0.5ml) at room temperature under a nitrogen atmosphere. The resulting mixture was heated to 40 0C for 24hrs before cooling to room temperature and evaporating in vacuo. The residue was purified by column chromatography using ethyl acetate as eluent to give 62mg of A1.13. LC/MS Phenomenex S5 4.6x30mm (2min gradient) Found: M+H = 378.27 at 1.51 min

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. 914942-88-4, tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 914942-88-4, name is tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C13H18IN5O2

A1.12 (1.48 g, 3.66 mmol), dichlorobis(triphenylphosphine)palladium (155 mg, 0.22 mmol), 3-ethynylbenzonitrile (A2.2) (930 mg, 7.32 mmol) and triethylamine (12 mL) were added to N,N-dimethylformamide (8 mL). The reaction mixture was heated at 90 0C for 50 min, cooled and the solvent removed under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as the eluent to provide 960mg (65%) of A2.3. M+H+ = 403.21. Alternate preparation:A1.12 (8.0 g, 19.85 mmol), dichlorobis(trirhohenylphosphine)palladium (840 mg, 1.2 mmol), 3-ethynylbenzonitrile (A2.2) (3.2g, 25.0 mmol) and triethylamine (60 mL) were each added to N,N-dimethylformamide (40 mL), and nitrogen was bubbled through the resulting mixture for 5min. The reaction mixture was heated at 90 0C for 20 min under a nitrogen atmosphere before cooling to room temperature and evaporating the solvent in vacuo. The residue was purified by silica gel column chromatography using ethyl acetate as eluent to provide 6.5g (81%) of A2.3 HPLC YMC S-5 4.6x33mm (2min grad): retention time 2.80min, M+H4″ = 403.21

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 914942-88-4, tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1220910-89-3 , The common heterocyclic compound, 1220910-89-3, name is Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate, molecular formula is C21H17FN6O2, 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.

To the kettle was added tetrahydrofuran (20 L)And benzyl N- [3-fluoro-4- [6- (2-methyl- 2H- tetrazolium- 5 -yl) -3-pyridyl] phenyl] carbamateCompound (II) (1 Kg, 2.47 mol),0 ~ 30 C After mixing,1,3-Dimethyl-3,4,5,6-tetrahydro-2-pyrimidone was added sequentially (DMPU, 0.63 Kg, 4.94 mol, 2 equivalents),Lithium tert-butoxide (0.396 Kg, 4.94 mol, 2 equivalents)Add R-glycidyl butyrate(0.39 Kg, 2.72 mol, 1.1 equivalents)0 ~ 30 C for 15 hours.After the reaction,The reaction was quenched by adding a mass-volume ammonium chloride solution (1 Kg / 10 L)Concentrated under reduced pressure,The residue was added to methanol (10 L)Stirred for 0.5 hours to give suction filtration,The filter cake was washed with methanol,45 ~ 50 C under vacuum to give a white solid(5R) -3- (4- (6- (2-methyl- 2H- tetrazolium- 5-yl) -3-pyridyl) -3- fluorophenyl) -5-hydroxymethyl oxazoline -2-one Compound (III) (0.87 Kg, yield: 95%).

The synthetic route of 1220910-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing You Ke Pharmaceutical Co., Ltd.; Nanjing You Ke Bio-pharmaceutical Co., Ltd.; Nanjing You Ke Bio-pharmaceutical Group Co., Ltd.; Li Shang; Che Xiaoming; Zhao Zanzan; Zhu Suhua; Xue Yuquan; Zhang Feng; (7 pag.)CN106317114; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1220910-89-3, 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. 1220910-89-3, name is Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate. A new synthetic method of this compound is introduced below.

Under the protection of nitrogen, to a 100 L reactor, 2.60 kg (6.43 mol) of terdazolamide phosphate intermediate II and 50 L of anhydrous tetrahydrofuran were added and stirred to dissolve. 7.07 liters of 1 mol / L lithium hexamethyldisilazide in tetrahydrofuran solution was added dropwise.Stir at 10 15 for 2 hours, add 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone (DMPU) 0.83Kg, and lower the temperature to 0 5 . Add R-glycidyl butyrate 0.97Kg. Stir overnight at 10 C to 15 C to obtain a light yellow slurry.A solution of 33 g of sodium methoxide dissolved in 330 mL of methanol was added and stirred for 1 hour. Add ammonium chloride solution with a mass concentration of 10% (the mass concentration means the mass of ammonium chloride as a percentage of the total mass of ammonium chloride water) 17L.The two-phase mixture was concentrated. Water (13 L, 5 volumes) was added to the concentrated slurry, cooled to room temperature, and filtered. The filter cake was slurried with methanol and water (volume ratio 4: 1) (70 L), then filtered, and filtered The cake was rinsed with 12L of methanol and 12L of water, and the wet product was dried in a vacuum (pressure -0.01MPa -0.1MPa) drying oven at 45 C- 55 C for 8 hours 12 hours to obtain the white solid as terdazolamide phosphate intermediate V 2.01Kg, yield 84.4%. HPLC purity: 99.21%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1220910-89-3, its application will become more common.

Reference:
Patent; Shanghai Bozhi Yan Xin Pharmaceutical Co., Ltd.; Chen Jian; Liu Zhenfeng; Ying Shuhuan; (16 pag.)CN110804038; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1142363-52-7, 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. 1142363-52-7, name is JNJ-40346527. A new synthetic method of this compound is introduced below.

Example 24 4-Cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide methanesulfonic acid salt A solution of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (50.0 mg, 0.108 mmol, as prepared in Example 15, step (h)) in EtOH (2 mL) was treated with methanesulfonic acid (7.0 muL, 0.108 mmol) at room temperature for 1 h. The solvents were evaporated in vacuo, and the residue was dried under high vacuum overnight. The solid was dissolved in a minimum amount of EtOH (2 mL) with sonication and heating. While warm, the solution was slowly treated with hexanes (3 mL) to the cloud point. The mixture was heated again until clear, the sides of the vial were scratched, and the mixture was allowed to cool. The solid was filtered and air-dried to afford the title compound (24 mg, 40%) as white crystals. Mass spectrum (APCI, m/z): Calcd. for C27H35N5O2, 462.3 (M+H), found 462.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1142363-52-7, JNJ-40346527, and friends who are interested can also refer to it.

Reference:
Patent; Illig, Carl R.; Chen, Jinsheng; Meegalia, Sanath K.; Wall, Mark J.; US2009/105296; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1142363-52-7, 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. 1142363-52-7, name is JNJ-40346527, molecular formula is C27H35N5O2, 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.

Example 31 4-Cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide sulfate salt A suspension of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (24.8 mg, 0.0537 mmol), as prepared in Example 15, in acetonitrile (1.0 mL) was heated to yield a solution. To the solution was added a solution of concentrated sulfuric acid (0.0062 mL) in water (0.5 mL) at room temperature. The solution was reduced via evaporation with flowing nitrogen gas (approximately 1.0 mL). The solution was then allowed to sit overnight at room temperature in a sealed vial. The resulting crystals were then collected via filtration and air-dried. The white solid was characterized by Powder X-Ray Diffraction (PXRD), Differential Scanning Calorimetry (DSC), Thremogravimetric Analysis (TGA), and single-crystal X-ray diffraction. The DSC for the sulfate salt showed a 241 degree Celsius endotherm maximum. The PXRD of the sulfate salt product is shown in and the prominent peaks are shown in the table below. Representative 2-Theta peaks of the sulfate salt product are shown below:

According to the analysis of related databases, 1142363-52-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Illig, Carl R.; Chen, Jinsheng; Meegalia, Sanath K.; Wall, Mark J.; US2009/105296; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1220910-89-3, 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. 1220910-89-3, name is Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate. A new synthetic method of this compound is introduced below.

Under the protection of nitrogen, to a 100 L reactor, 2.60 kg (6.43 mol) of terdazolamide phosphate intermediate II and 50 L of anhydrous tetrahydrofuran were added and stirred to dissolve. 7.07 liters of 1 mol / L lithium hexamethyldisilazide in tetrahydrofuran solution was added dropwise.Stir at 10 15 for 2 hours, add 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone (DMPU) 0.83Kg, and lower the temperature to 0 5 . Add R-glycidyl butyrate 0.97Kg. Stir overnight at 10 C to 15 C to obtain a light yellow slurry.A solution of 33 g of sodium methoxide dissolved in 330 mL of methanol was added and stirred for 1 hour. Add ammonium chloride solution with a mass concentration of 10% (the mass concentration means the mass of ammonium chloride as a percentage of the total mass of ammonium chloride water) 17L.The two-phase mixture was concentrated. Water (13 L, 5 volumes) was added to the concentrated slurry, cooled to room temperature, and filtered. The filter cake was slurried with methanol and water (volume ratio 4: 1) (70 L), then filtered, and filtered The cake was rinsed with 12L of methanol and 12L of water, and the wet product was dried in a vacuum (pressure -0.01MPa -0.1MPa) drying oven at 45 C- 55 C for 8 hours 12 hours to obtain the white solid as terdazolamide phosphate intermediate V 2.01Kg, yield 84.4%. HPLC purity: 99.21%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1220910-89-3, its application will become more common.

Reference:
Patent; Shanghai Bozhi Yan Xin Pharmaceutical Co., Ltd.; Chen Jian; Liu Zhenfeng; Ying Shuhuan; (16 pag.)CN110804038; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1142363-52-7, 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. 1142363-52-7, name is JNJ-40346527. A new synthetic method of this compound is introduced below.

Example 24 4-Cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide methanesulfonic acid salt A solution of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (50.0 mg, 0.108 mmol, as prepared in Example 15, step (h)) in EtOH (2 mL) was treated with methanesulfonic acid (7.0 muL, 0.108 mmol) at room temperature for 1 h. The solvents were evaporated in vacuo, and the residue was dried under high vacuum overnight. The solid was dissolved in a minimum amount of EtOH (2 mL) with sonication and heating. While warm, the solution was slowly treated with hexanes (3 mL) to the cloud point. The mixture was heated again until clear, the sides of the vial were scratched, and the mixture was allowed to cool. The solid was filtered and air-dried to afford the title compound (24 mg, 40%) as white crystals. Mass spectrum (APCI, m/z): Calcd. for C27H35N5O2, 462.3 (M+H), found 462.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1142363-52-7, JNJ-40346527, and friends who are interested can also refer to it.

Reference:
Patent; Illig, Carl R.; Chen, Jinsheng; Meegalia, Sanath K.; Wall, Mark J.; US2009/105296; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1142363-52-7, 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. 1142363-52-7, name is JNJ-40346527, molecular formula is C27H35N5O2, 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.

Example 31 4-Cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide sulfate salt A suspension of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (24.8 mg, 0.0537 mmol), as prepared in Example 15, in acetonitrile (1.0 mL) was heated to yield a solution. To the solution was added a solution of concentrated sulfuric acid (0.0062 mL) in water (0.5 mL) at room temperature. The solution was reduced via evaporation with flowing nitrogen gas (approximately 1.0 mL). The solution was then allowed to sit overnight at room temperature in a sealed vial. The resulting crystals were then collected via filtration and air-dried. The white solid was characterized by Powder X-Ray Diffraction (PXRD), Differential Scanning Calorimetry (DSC), Thremogravimetric Analysis (TGA), and single-crystal X-ray diffraction. The DSC for the sulfate salt showed a 241 degree Celsius endotherm maximum. The PXRD of the sulfate salt product is shown in and the prominent peaks are shown in the table below. Representative 2-Theta peaks of the sulfate salt product are shown below:

According to the analysis of related databases, 1142363-52-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Illig, Carl R.; Chen, Jinsheng; Meegalia, Sanath K.; Wall, Mark J.; US2009/105296; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 940943-37-3 , The common heterocyclic compound, 940943-37-3, name is S-(2-(6-(4-(3-(Dimethylamino)propoxy)phenylsulfonamido)pyridin-3-yl)-2-oxoethyl) ethanethioate, molecular formula is C20H25N3O5S2, 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.

[0202] Into 0.3088 g of Compound 1 was added 2 mL of methanol and 1.0 molar equivalent of hydrochloric acid (0.5 M in methanol, made from concentrated aqueous HCl solution) at approximately 60 0C. An additional 0.5 mL of methanol was added and the solution left to stir until only a small amount of solid remained. The sample was filtered through a 0.2 micron nylon filter. Seeds of HCl A were added and dissolved immediately upon addition. The solution was allowed to cool slowly to ambient temperature. Additional seeds (HCl A) were added and a light yellow precipitation followed. The solids were isolated by vacuum filtration and stored in a P205 desiccator (0.2373 g; yield 71%, based on unsolvated weight).

The synthetic route of 940943-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; WO2008/73733; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem