Category: 201937-23-7

Reference of 201937-23-7 ,Some common heterocyclic compound, 201937-23-7, molecular formula is C6H7Cl2N3, 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.

Compound 88 (1.08 g, 3.14 mmol), 6-chloropyridine-3-carboxirnidamide hydrochloride (900 mg, 4.69 mmol) and K2CO3 (1.30 g, 9.42 mmol) in EtOH (15 mL) were heated in a Biotage microwave synthesizer at 120 C for 3 h. After the reaction was cooled to room temperature, EtOAc was added. The mixture was washed with water. The organic extract was dried with Na2S04and concentrated. The crude product was dissolved in CH2CI2 (31 mL) and treated with DDQ (713 mg, 3.14 mmol). After the reaction was stirred at room temperature for 1 h, aq. sat. NaHCCb was added. The mixture was stirred at room temperature for 10 min; filtered through a pad of Celite; and eluted with CH2CI2. The organic phase of the filtrate was separated. The aqueous phase was extracted with CH2CI2. The combined organic extract was dried with Na2S04 and filtered and concentrated. The residue was purified by flash chromatography (silica gel, eluting with 0% to 5% EtOAc in CH2CI2) to give compound 363 (902 g, 60% yield) as a white foamy solid, m/z = 480 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,201937-23-7, its application will become more common.

Reference:
Patent; REATA PHARMACEUTICALS, INC.; JIANG, Xin; BENDER, Christopher, F.; VISNICK, Melean; HOTEMA, Martha, R.; SHELDON, Zachary, S.; LEE, Chitase; CAPRATHE, Bradley, William; BOLTON, Gary; KORNBERG, Brian; (497 pag.)WO2018/111315; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 201937-23-7, 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. 201937-23-7, name is 6-Chloronicotinimidamide hydrochloride. A new synthetic method of this compound is introduced below.

2-(6-chloropyridin-3-yl)-N-(l-methyl-lH-pyrazol-4-yl)-4-(propan-2-yloxy)-7,8-dihydropyrido- [4,3-d]pyrimidine-6(5H)-carboxamide (K-2)A mixture of unpurified K-I (12.5 g, 42.5 mmol), 6-chloropyridine-3- carboximidamide hydrochloride (12.2 g, 54.0 mmol), and K2CO3 (17.61 g, 127 mmol) was diluted with DMF (140 ml) and treated with 2-iodopropane (10.62 ml, 106 mmol) in a 1-L round bottom flask with stirring. The reaction mixture was heated to 65 ºC and stirred for 3 h. The mixture was removed from heat and treated with 1.5 L H2O in a 3 -L Erlenmeyer flask to precipitate desired product. The mixture was stirred vigorously for 1 h and filtered through a coarse scintered glass funnel. The wet paste was transferred to a 1-L round bottom flask with toluene (300 mL) and acetone (300 mL) and concentrated in vacuo. The resulting residue was subjected to a second toluene (400 mL) azeotrope. The solids were dried under high vacuum over the weekend. The solids were suspended in 800 mL chloroform and heated to 40 ºC with stirring for 1 hr. The hazy solution was filtered through Celite, and the filtrate was concentrated in vacuo. The resulting off white foam (-12.5 g) was diluted with EtOH (1 L) and stirred at 85 ºC for 1 hr until a clear solution persisted. The solution was cooled RT and concentrated to dryness. The solids were stirred vigorously in Et2O (750 mL) for 15 min, and the mixture was filtered through a large scintered glass funnel. The solids were washed with diethyl ether (3x 350 mL), air-dried under vacuum for 10 min, and then dried under high vacuum for 24 h with routine agitation to afford the title compound (11.5, 63%) as a white solid. Data for K-2: 1H NMR (500 MHz, CDCl3) delta 9.36 (d, J= 1.7, IH), 8.61 (dd, J= 8.3, 2.2 Hz, IH), 7.75 (s, IH), 7.41 (d, J= 8.3 Hz, IH), 7.40 (s, IH), 6.40 (s, IH), 5.60 (hept, J= 6.2 Hz, IH), 4.50 (s, 2H), 3.88 (s, 3H), 3.84 (t, J= 5.6 Hz, 2H), 3.01 (t, J= 5.6 Hz, 2H), 1.46 (d, J= 6.2 Hz, 6H); HRMS m/z (M+H) 424.1561 found, 424.1535 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,201937-23-7, its application will become more common.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BRESLIN, Michael, J.; COLEMAN, Paul, J.; COX, Christopher, D.; RAHEEM, Izzat, T.; SCHREIER, John, D.; WO2010/138430; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 201937-23-7 ,Some common heterocyclic compound, 201937-23-7, molecular formula is C6H7Cl2N3, 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.

Compound 88 (1.08 g, 3.14 mmol), 6-chloropyridine-3-carboxirnidamide hydrochloride (900 mg, 4.69 mmol) and K2CO3 (1.30 g, 9.42 mmol) in EtOH (15 mL) were heated in a Biotage microwave synthesizer at 120 C for 3 h. After the reaction was cooled to room temperature, EtOAc was added. The mixture was washed with water. The organic extract was dried with Na2S04and concentrated. The crude product was dissolved in CH2CI2 (31 mL) and treated with DDQ (713 mg, 3.14 mmol). After the reaction was stirred at room temperature for 1 h, aq. sat. NaHCCb was added. The mixture was stirred at room temperature for 10 min; filtered through a pad of Celite; and eluted with CH2CI2. The organic phase of the filtrate was separated. The aqueous phase was extracted with CH2CI2. The combined organic extract was dried with Na2S04 and filtered and concentrated. The residue was purified by flash chromatography (silica gel, eluting with 0% to 5% EtOAc in CH2CI2) to give compound 363 (902 g, 60% yield) as a white foamy solid, m/z = 480 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,201937-23-7, its application will become more common.

Reference:
Patent; REATA PHARMACEUTICALS, INC.; JIANG, Xin; BENDER, Christopher, F.; VISNICK, Melean; HOTEMA, Martha, R.; SHELDON, Zachary, S.; LEE, Chitase; CAPRATHE, Bradley, William; BOLTON, Gary; KORNBERG, Brian; (497 pag.)WO2018/111315; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 201937-23-7, 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. 201937-23-7, name is 6-Chloronicotinimidamide hydrochloride. A new synthetic method of this compound is introduced below.

2-(6-chloropyridin-3-yl)-N-(l-methyl-lH-pyrazol-4-yl)-4-(propan-2-yloxy)-7,8-dihydropyrido- [4,3-d]pyrimidine-6(5H)-carboxamide (K-2)A mixture of unpurified K-I (12.5 g, 42.5 mmol), 6-chloropyridine-3- carboximidamide hydrochloride (12.2 g, 54.0 mmol), and K2CO3 (17.61 g, 127 mmol) was diluted with DMF (140 ml) and treated with 2-iodopropane (10.62 ml, 106 mmol) in a 1-L round bottom flask with stirring. The reaction mixture was heated to 65 ºC and stirred for 3 h. The mixture was removed from heat and treated with 1.5 L H2O in a 3 -L Erlenmeyer flask to precipitate desired product. The mixture was stirred vigorously for 1 h and filtered through a coarse scintered glass funnel. The wet paste was transferred to a 1-L round bottom flask with toluene (300 mL) and acetone (300 mL) and concentrated in vacuo. The resulting residue was subjected to a second toluene (400 mL) azeotrope. The solids were dried under high vacuum over the weekend. The solids were suspended in 800 mL chloroform and heated to 40 ºC with stirring for 1 hr. The hazy solution was filtered through Celite, and the filtrate was concentrated in vacuo. The resulting off white foam (-12.5 g) was diluted with EtOH (1 L) and stirred at 85 ºC for 1 hr until a clear solution persisted. The solution was cooled RT and concentrated to dryness. The solids were stirred vigorously in Et2O (750 mL) for 15 min, and the mixture was filtered through a large scintered glass funnel. The solids were washed with diethyl ether (3x 350 mL), air-dried under vacuum for 10 min, and then dried under high vacuum for 24 h with routine agitation to afford the title compound (11.5, 63%) as a white solid. Data for K-2: 1H NMR (500 MHz, CDCl3) delta 9.36 (d, J= 1.7, IH), 8.61 (dd, J= 8.3, 2.2 Hz, IH), 7.75 (s, IH), 7.41 (d, J= 8.3 Hz, IH), 7.40 (s, IH), 6.40 (s, IH), 5.60 (hept, J= 6.2 Hz, IH), 4.50 (s, 2H), 3.88 (s, 3H), 3.84 (t, J= 5.6 Hz, 2H), 3.01 (t, J= 5.6 Hz, 2H), 1.46 (d, J= 6.2 Hz, 6H); HRMS m/z (M+H) 424.1561 found, 424.1535 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,201937-23-7, its application will become more common.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BRESLIN, Michael, J.; COLEMAN, Paul, J.; COX, Christopher, D.; RAHEEM, Izzat, T.; SCHREIER, John, D.; WO2010/138430; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 201937-23-7, name is 6-Chloronicotinimidamide hydrochloride. A new synthetic method of this compound is introduced below., name: 6-Chloronicotinimidamide hydrochloride

2-(6-chloropyridin-3-yl)-4-(2-methoxyethoxy)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (O-l) A suspension of 1-tert-butyl 3 -ethyl 4-oxopiperidine-l,3-dicarboxylate (A-I, 41.5 g, 153 mmol), -chloropyridine-S-carboximidamide hydrochloride (43.9 g, -85% pure, 194 mmol), and K2CO3 (59.8 g, 433 mmol) in DMF (457 mL) was treated with 2-bromoethyl methyl ether (26.3 ml, 280 mmol) with stirring. The mixture was heated to 65 ºC and stirred for 24 hr, adding additional small equivalents of 2-bromoethyl methyl ether and K2CO3 to drive reaction to completion if needed. The reaction mixture was diluted with EtOAc (1.5 L), and washed with water (2 L), sat. aq. NaHCO3 (2 L), water (2 L), and brine (1 L). The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to provide unpurified Boc-protected intermediate (~62 g), which was used in the subsequent step without further purification.

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Reference:
Patent; MERCK SHARP &; DOHME CORP.; BRESLIN, Michael, J.; COLEMAN, Paul, J.; COX, Christopher, D.; RAHEEM, Izzat, T.; SCHREIER, John, D.; WO2010/138430; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem