Category: 62002-31-7

Synthetic Route of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

To a stirred solution of 1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine dihydrochloride (7 g, 35.70 mmol, 1 equiv.) and 4,5-dichloro-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (10.7 g, 42.84 mmol, 1.2 equiv.) in DMA(100 mL) was added DIEA(13.8 g, 107.10 mmol, 3 equiv.) in portions at room temperature under nitrogen atmosphere. The resulting mixture was stirred for overnight at 100 degrees Celsius under nitrogen atmosphere. The reaction was monitored by LCMS. The resulting mixture was extracted with EtOAc (100 x mL). The combined organic layers were washed with brine (3×100 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. This resulted in 4-chloro-2-(oxan-2-yl)-5- [1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridin-5-yl]-2,3-dihydropyridazin-3-one (8.5 g, 70.91%) as a light y

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62002-31-7, 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

To a stirred solution of 1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine dihydrochloride (7 g, 35.70 mmol, 1 equiv.) and 4,5-dichloro-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (10.7 g, 42.84 mmol, 1.2 equiv.) in DMA(100 mL) was added DIEA(13.8 g, 107.10 mmol, 3 equiv.) in portions at room temperature under nitrogen atmosphere. The resulting mixture was stirred for overnight at 100 degrees Celsius under nitrogen atmosphere. The reaction was monitored by LCMS. The resulting mixture was extracted with EtOAc (100 x mL). The combined organic layers were washed with brine (3×100 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. This resulted in 4-chloro-2-(oxan-2-yl)-5- [1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridin-5-yl]-2,3-dihydropyridazin-3-one (8.5 g, 70.91%) as a light y

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62002-31-7, 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

To a stirred solution of 1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine dihydrochloride (7 g, 35.70 mmol, 1 equiv.) and 4,5-dichloro-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (10.7 g, 42.84 mmol, 1.2 equiv.) in DMA(100 mL) was added DIEA(13.8 g, 107.10 mmol, 3 equiv.) in portions at room temperature under nitrogen atmosphere. The resulting mixture was stirred for overnight at 100 degrees Celsius under nitrogen atmosphere. The reaction was monitored by LCMS. The resulting mixture was extracted with EtOAc (100 x mL). The combined organic layers were washed with brine (3×100 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. This resulted in 4-chloro-2-(oxan-2-yl)-5- [1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridin-5-yl]-2,3-dihydropyridazin-3-one (8.5 g, 70.91%) as a light y

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62002-31-7, 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

Iminodibenzyl (50.0 g, 0.256 mol) was dissolved in DMF (700 mL), sodium hydride (12.3 g, 0.306 mol, 60% dispersion in oil) was slowly added in portions and the mixture was stirred at 50 C. for 2 h. Ethyl 3-bromopropionate (100 mL, 0.77 mol) was slowly added dropwise and the mixture was heated at reflux temperature overnight. The mixture was cooled and evaporated. The residue was suspended in DCM (150 mL), filtered and the solvent was evaporated. The resulting residue was purified in portions by column chromatography (silica gel, DCM) to give 5.1 g (7%) of 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid ethyl ester.TLC: Rf=0.69 (silica gel, DCM).3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid ethyl ester (1.41 g, 4.77 mmol) was dissolved in ethanol (30 mL) and a solution of sodium hydroxide (0.75 g, 18.8 mmol) in water (5 mL) was added. The mixture was stirred for 3.5 h. 1 N Hydrochloric acid (17 mL) was added and the mixture was extracted with DCM (2×25 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO4) and the solvent was evaporated to give 1.18 g (92%) of 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid.Carbonyldiimidazole (0.33 g, 2.1 mmol) was dissolved in DCM (5 mL) and 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propionic acid (0.56 g, 2.1 mmol) was added. The mixture was stirred at room temperature for 1.5 h under a nitrogen atmosphere. Simultaneously, sodium methoxide (0.8 mL of a 30% solution in water, 4.4 mmol) was added to a solution of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (0.43 g, 2.2 mmol) in methanol (5 mL). The mixture was stirred at room temperature for 1.5 h under a nitrogen atmosphere. The solvent was evaporated and the residue was stripped with DCM (6 mL). The above solution of the activated carboxylic acid was added to the residue and the reaction mixture was stirred at room temperature overnight. Water (10 mL) was added followed by DCM (50 mL) and the phases were separated. The aqueous phase was extracted with DCM (20 mL) and the combined organic phases were dried (MgSO4). After evaporation of the solvent, the residue was purified by column chromatography (silica gel, 150 mL, methanol/ethyl acetate 1:5). Evaporation of the solvent afforded 0.41 g (52%) of the title compound as a solid.TLC: Rf=0.28 (silica gel, methanol/ethyl acetate 1:5). LC-MS: Calcd. for MH+: 373; found: 373.1H NMR (400 MHz, DMSO-d6, two rotamers, 1:1): delta2.49 (m, 1H), 2.60-2.72 (m, 3H), 3.07 (d, 4H), 3.47 (t, 1H), 3.86 (t, 1H), 4.08-4.20 (m, 2H), 4.22 (s, 1H), 4.62 (s, 1H), 6.90 (m, 2H), 7.01-7.16 (m, 6H), 7.40 (s, 0.5H), 7.45 (s, 0.5H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62002-31-7, its application will become more common.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62002-31-7, 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 62002-31-7 as follows.

To a stirred solution of 4,5-dibromo-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (3 g, 8.88 mmol, 1 equiv.) and 1H,4H,5H,6H,7H-imidazo [4,5-c]pyridine (1.1 g, 8.88 mmol, 1.00 equiv.) in 1,4- dioxane (30 mL) was added DIEA (2.3 g, 17.75 mmol, 2 equiv.) dropwise at 0 degree Celsius under nitrogen atmosphere. The mixture was stirred at 100 degrees Celsius overnight. Desired product could be detected by LCMS. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with CH2Cl2 / MeOH (10:1 to 5:1) to afford 4-bromo-5-[1H,4H,5H,6H,7H-imidazo[4,5-c]pyridin-5-yl]-2- (oxan-2-yl)-2,3-dihydropyridazin-3-one (3g, 88.89%) as white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62002-31-7, its application will become more common.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 62002-31-7, 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, 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, Safety of 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, blongs to pyridine-derivatives compound. Safety of 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride

At 0 C., EDC (0.45 g, 2.4 mmol) was added to a solution of 1-hydroxy-7-azabenzotriazole (0.32 g, 2.4 mmol) and 2-norbornaneacetic acid (0.338 mL, 2.4 mmol) in dichloromethane (30 mL). The reaction mixture was stirred for 20 min at 0 C. 4,5,6,7-Tetrahydroimidazo[4,5-c]pyridine dihycrochloride (0.50 g, 2.3 mmol) was added. Ethyldiisopropylamine (0.40 mL, 2.3 mmol) was added. The reaction mixture was stirred for 16 h at room temperature. It was diluted with ethyl acetate (100 mL) and washed with a saturated aqueous solution of sodium hydrogencarbonate (100 mL). The aqueous solution was extracted with ethyl acetate (2*60 mL). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 120 mg of the title compound. 1H NMR (CDCl3, 2 rotamers): delta 1.00-2.50 (m, 13H); 2.65 and 2.75 (both t, together 2H); 3.75 and 3.90 (both t, together 2H); 4.55 and 4.65 (both s, together 2H); 7.53 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62002-31-7, 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

To a mixture of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (0.50 g, 2.55 mmol), ethanol (10 mL) and triethylamine (1.10 mL, 7.89 mmol), 2,4-dichlorobenzyl isocyanate (0.52 g, 2.57 mmol) was added. The resulting mixture was stirred at room temperature for 16 h and then concentrated under reduced pressure. The residue was distributed between water (20 mL) and ethyl acetate (75 mL). The organic phase was washed with water (10 mL) and brine (10 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was triturated in diethylether (50 mL) and the crude product was filtered off. Recrystallization from acetone (25 mL) gave 0.30 g (37%) of the title ureaurea as a colourless solid. HPLC (214 nm): elution at 7.97 min. LC-MS: Calcd. for MH+: 325; found: 325. 1H NMR (400 MHz, DMSO-d6): delta2.56 (s, br, 2H), 3.65 (t, J=6 Hz, 2H), 4.29 (d, J=6 Hz, 2H), 4.34 (s, 2H), 7.20 (s, br, 1H), 7.29 (d, J=8 Hz, 1H), 7.39 (dd, J=8, 1 Hz, 1H), 7.47 (s, 1H), 7.56 (d, J=1 Hz, 1H), 11.79 (s, br, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62002-31-7, its application will become more common.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, molecular formula is C6H11Cl2N3, 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.

1-Hydroxy-7-azabenzotriazole (0.32 g, 2.4 mmol) was added to a solution of phenylpropiolic acid (0.34 g, 2.4 mmol) in dichloromethane (30 mL). The solution was cooled to 0 C. EDC (0.45 g, 2.4 mmol) was added. The reaction mixture was stirred at 0 C. for 20 min. 4,5,6,7-Tetrahydroimidazo[4,5-c]pyridine dihycrochloride (0.50 g, 2.3 mmol) was added. Ethyldiisopropylamine (0.40 mL, 2.3 mmol) was added. The reaction mixture was stirred for 16 h at room temperature. It was diluted with ethyl acetate (100 mL) and washed with 10% aqueous sodium hydrogensulfate solution (100 mL). The aqueous phase was extracted with ethyl acetate (3*60 mL): It was added a 1 N sodium hydroxide solution until pH 12 was obtained. It was extracted with ethyl acetate (3*90 mL). These extracts were combined and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 50 mg of the title compound. 1H NMR (CDCl3, 2 rotamers): delta2.75 and 2.85 (both t, together 2H); 4.03 and 4.15 (both t, together 2H); 4.75 and 4.92 (both s, together 1H); 7.10-7.70 (m, 6H).

According to the analysis of related databases, 62002-31-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem