Category: 63237-88-7

Electric Literature of 63237-88-7 ,Some common heterocyclic compound, 63237-88-7, molecular formula is C8H6N2O2, 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: A solution of P(OMe)3 (1.5mmol) in DCM (10mL) was cooled with an ice bath, then I2 (1.5mmol) was added. After the solid iodine was completely dissolved, corresponding acid (1.2mmol) and Et3N (3.0mmol) were added in sequential order, and the solution was stirred for 15min in a cooling bath. Intermediate 5 (1.0mmol) was added and the mixture was stirred for 15min. After removing the cooling bath, the reaction mixture was stirred for 3.5hat room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10mL) three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (100:1 to 50:1, v/v) to give the product as a white solid.

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. 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bai, Renren; Shi, Qi; Liang, Zhongxing; Yoon, Younghyoun; Han, Yiran; Feng, Amber; Liu, Shuangping; Oum, Yoonhyeun; Yun, C. Chris; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 464 – 475;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7, 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. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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 12N-[6-(1 H-lndol-4-yl)-1 H-indazol-4-yl]pyrazolo[1 ,5-a]pyridine-2-carboxamide Pyrazolo[1 ,5-a]pyridine-2-carboxylic acid (27 mg, 0.166 mmol) was treated with anhydrous THF (2ml) and then 1-chloro-N, N, 2-trimethylpropenylamine (0.026 ml, 0.20 mmol). The reaction was stirred at room temperature under nitrogen for 2 hrs. The reaction was then treated with anhydrous DIPEA (0.131 ml, 0.753 mmol) and 2ml of solution of 6-(1 H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (750mg, 2.26 mmol) in THF (30ml). The reaction was then stirred at room temperature under nitrogen for 69 hrs. The solvent was blown -off under a stream of nitrogen, dissolved in methanol (3ml) and then solvent removed under reduced pressure. The crude reaction mixture was dissolved in methanol (5ml), treated with Macroporous Tosic Acid (4.45 mmol/g, 102 mg, 0.45 mmol), stirred at room temperature for 17 hrs and then treated with 0.88 ammonia (0.5 ml), stirred for 30 minutes and then filtered. The solvent was removed under reduced pressure and then the residue purified by Mass Directed Automated Preparative HPLC (Method B) to give the title compound. LCMS (Method B) m/z 393 [MH+], R1 = 1.02min.

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147189; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7 ,Some common heterocyclic compound, 63237-88-7, molecular formula is C8H6N2O2, 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: A solution of P(OMe)3 (1.5mmol) in DCM (10mL) was cooled with an ice bath, then I2 (1.5mmol) was added. After the solid iodine was completely dissolved, corresponding acid (1.2mmol) and Et3N (3.0mmol) were added in sequential order, and the solution was stirred for 15min in a cooling bath. Intermediate 5 (1.0mmol) was added and the mixture was stirred for 15min. After removing the cooling bath, the reaction mixture was stirred for 3.5hat room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10mL) three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (100:1 to 50:1, v/v) to give the product as a white solid.

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. 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bai, Renren; Shi, Qi; Liang, Zhongxing; Yoon, Younghyoun; Han, Yiran; Feng, Amber; Liu, Shuangping; Oum, Yoonhyeun; Yun, C. Chris; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 464 – 475;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7, 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. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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 12N-[6-(1 H-lndol-4-yl)-1 H-indazol-4-yl]pyrazolo[1 ,5-a]pyridine-2-carboxamide Pyrazolo[1 ,5-a]pyridine-2-carboxylic acid (27 mg, 0.166 mmol) was treated with anhydrous THF (2ml) and then 1-chloro-N, N, 2-trimethylpropenylamine (0.026 ml, 0.20 mmol). The reaction was stirred at room temperature under nitrogen for 2 hrs. The reaction was then treated with anhydrous DIPEA (0.131 ml, 0.753 mmol) and 2ml of solution of 6-(1 H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (750mg, 2.26 mmol) in THF (30ml). The reaction was then stirred at room temperature under nitrogen for 69 hrs. The solvent was blown -off under a stream of nitrogen, dissolved in methanol (3ml) and then solvent removed under reduced pressure. The crude reaction mixture was dissolved in methanol (5ml), treated with Macroporous Tosic Acid (4.45 mmol/g, 102 mg, 0.45 mmol), stirred at room temperature for 17 hrs and then treated with 0.88 ammonia (0.5 ml), stirred for 30 minutes and then filtered. The solvent was removed under reduced pressure and then the residue purified by Mass Directed Automated Preparative HPLC (Method B) to give the title compound. LCMS (Method B) m/z 393 [MH+], R1 = 1.02min.

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147189; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63237-88-7, Adding some certain compound to certain chemical reactions, such as: 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid,molecular formula is C8H6N2O2, 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 63237-88-7.

Step 2B: Synthesis of N-{4-[(pyrimidin-2-yl)({[2-(trimethylsilyl)ethoxy]methyl}) sulfamoyl] phenyl}pyrazolo[l,5-a]pyridine-2-carboxamide 13.1 [00307] Methanesulfonyl chloride (0.04ml, 0.55mmol) was added to a stirred mixture of 4- amino-N-(pyrimidin-2-yl)-N- { [2-(trimethylsilyl)ethoxy]methyl} benzene- 1 -sulfonamide (9.1, 150mg, 0.39mmol), pyrazolo[l,5-a]pyridine-2-carboxylic acid (60mg, 0.39mmol) and 3-picoline (0.12 ml, 1.18mmol) in MeCN (dry, 5ml) at 0C. After addition the reaction mixture was allowed to reach rt and stirred for 15h. The reaction mixture was partitioned between DCM (50ml) and water (50ml). The aqueous layer was further extracted with DCM (2x 30ml) and the combined layers dried over Na2S04. The solvent was removed in vacuo to afford a material which was purified by flash column chromatography (heptane/EtOAc 75/25 to 0/100) to obtain 190mg (87%) of N-{4-[(pyrimidin-2-yl)({[2-(trimethylsilyl)ethoxy]methyl}) sulfamoyl]phenyl}pyrazolo[l,5-a]pyridine-2-carboxamide 13.1 as an off white solid.

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RAZE THERAPEUTICS, INC.; SAIAH, Eddine; (148 pag.)WO2016/40449; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7, 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 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 97N-((ls,4s)-4-(2-(4′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-3′-hydroxybiphenyl-3- yloxyJ-S-fluoronicotinamidoJcyclohexylJpyrazolo [ 1 ,5-a] pyridine-2-carboxamide To a solution of pyrazolo[l,5-a]pyridine-2-carboxylic acid (30.8 mg, 0.19 mmol) in acetonitrile (3 mL) was added DIPEA (0.066 mL, 0.38 mmol). To this mixture was then added HATU (72.3 mg, 0.19 mmol). The mixture was stirred at RT for 10 min before it was added to a solution of N-((ls,4s)-4-aminocyclohexyl)-2-(4′-(((3S,5R)-3,5-dimethylpiperazin- l-yl)methyl)-3′-hydroxybiphenyl-3-yloxy)-5-fluoronicotinamide, hydrochloride (125 mg, 0.19 mmol) and DIPEA (0.066 mL, 0.38 mmol) in acetonitrile (3 mL). The mixture was stirred at RT overnight. 1 mL water and 1 mL acetic acid was then added to the mixture before being purified using reverse phase preparative HPLC (eluent = TFA(aq)/MeCN). The appropriate fractions were combined and evaporated to give a residue. This was triturated with ether to give the title compound as a solid which was isolated by filtration and dried overnight under vacuum at 400C. Yield: 96 mg 1H NMR (400 MHz, CD3OD) delta 8.48 (d, J = 7.4 Hz, IH), 8.43 (d, J = 7.2 Hz, IH), 8.12 (d, J = 3.1 Hz, IH), 8.06 (dd, J = 7.9, 3.1 Hz, IH), 7.66 (d, J = 9.0 Hz, IH), 7.51 – 7.43 (m, 2H), 7.40 – 7.37 (m, IH), 7.25 – 7.17 (m, 3H), 7.10 – 7.07 (m, 2H), 6.97 – 6.93 (m, 2H), 4.17 – 4.11 (m, IH), 4.07 (s, IH), 4.04 – 3.99 (m, IH), 3.58 – 3.51 (m, 2H), 3.45 – 3.40 (m, 2H), 2.64 (t, J = 12.6 Hz, 2H), 1.92 – 1.70 (m, 8H), 1.31 (d, J = 6.4 Hz, 6H). MS: [M+H]+=692.2 (calc=692.336) (MultiMode+)

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7, 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 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 97N-((ls,4s)-4-(2-(4′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-3′-hydroxybiphenyl-3- yloxyJ-S-fluoronicotinamidoJcyclohexylJpyrazolo [ 1 ,5-a] pyridine-2-carboxamide To a solution of pyrazolo[l,5-a]pyridine-2-carboxylic acid (30.8 mg, 0.19 mmol) in acetonitrile (3 mL) was added DIPEA (0.066 mL, 0.38 mmol). To this mixture was then added HATU (72.3 mg, 0.19 mmol). The mixture was stirred at RT for 10 min before it was added to a solution of N-((ls,4s)-4-aminocyclohexyl)-2-(4′-(((3S,5R)-3,5-dimethylpiperazin- l-yl)methyl)-3′-hydroxybiphenyl-3-yloxy)-5-fluoronicotinamide, hydrochloride (125 mg, 0.19 mmol) and DIPEA (0.066 mL, 0.38 mmol) in acetonitrile (3 mL). The mixture was stirred at RT overnight. 1 mL water and 1 mL acetic acid was then added to the mixture before being purified using reverse phase preparative HPLC (eluent = TFA(aq)/MeCN). The appropriate fractions were combined and evaporated to give a residue. This was triturated with ether to give the title compound as a solid which was isolated by filtration and dried overnight under vacuum at 400C. Yield: 96 mg 1H NMR (400 MHz, CD3OD) delta 8.48 (d, J = 7.4 Hz, IH), 8.43 (d, J = 7.2 Hz, IH), 8.12 (d, J = 3.1 Hz, IH), 8.06 (dd, J = 7.9, 3.1 Hz, IH), 7.66 (d, J = 9.0 Hz, IH), 7.51 – 7.43 (m, 2H), 7.40 – 7.37 (m, IH), 7.25 – 7.17 (m, 3H), 7.10 – 7.07 (m, 2H), 6.97 – 6.93 (m, 2H), 4.17 – 4.11 (m, IH), 4.07 (s, IH), 4.04 – 3.99 (m, IH), 3.58 – 3.51 (m, 2H), 3.45 – 3.40 (m, 2H), 2.64 (t, J = 12.6 Hz, 2H), 1.92 – 1.70 (m, 8H), 1.31 (d, J = 6.4 Hz, 6H). MS: [M+H]+=692.2 (calc=692.336) (MultiMode+)

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); 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. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below., Product Details of 63237-88-7

Compound 5 was reported previously.30 For this study, 5 wasre synthesized using a modified synthesis as follows: To a solution of pyrazolo[1,5-a]pyridine-2-carboxylic acid (150 mg, 0.93 mmol)and 4 (230 mg, 0.93 mmol) in anhydrous DMF (5 mL) was added DIPEA (0.33 mL, 1.86 mmol) and HATU (372 mg, 0.98 mmol). After stirring the reaction mixture at room temperature for 16 h the solvent was removed under reduced pressure. The crude mixture was suspended in aqueous 5% NaHCO3 solution and extracted with ethyl acetate (3). The combined organic phases were washed with water and brine and were dried (MgSO4). After removal of solvents under reduced pressure the crude material was purified by flash chromatography (CH2Cl2/MeOH/NH3 aq., 20:1:0.01) to give5 (314 mg, 86%) as a colorless solid. 1H NMR (600 MHz, CDCl3) d8.38-8.34 (m, 1H), 7.61-7.51 (m, 1H), 7.29 (br s, J = 5.2 Hz, 1H),7.18-7.12 (m, 2H), 7.09-7.04 (m, 2H), 6.94 (dd, J = 8.0, 1.4 Hz,1H), 6.88-6.81 (m, 2H), 3.58-3.50 (m, 2H), 2.98-2.87 (m, 4H),2.63 (br s, 4H), 2.51-2.45 (m, 2H), 1.76-1.63 (m, 4H); 13C NMR(150 MHz, CDCl3) d 162.2, 151.5, 148.1, 141.4, 139.0, 128.4,126.4, 123.7, 121.5, 120.0, 119.3, 114.0, 113.6, 98.0, 58.1, 53.9,52.6, 39.1, 27.6, 24.4; ESI-MS m/z 394.2 [M+H]+.

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, 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid.

Reference:
Article; Stoessel, Anne; Brox, Regine; Purkayastha, Nirupam; Huebner, Harald; Hocke, Carsten; Prante, Olaf; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3491 – 3499;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63237-88-7 , The common heterocyclic compound, 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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.

Example 132N-((ls,4s)-4-(5-fluoro-2-(4′-(3-(piperazin-l-yl)propyl)biphenyl-3- yloxy)nicotinamido)cyclohexyl)pyrazolo [ 1 ,5-a] pyridine-2-carboxamide To a solution of tert-butyl 4-(3-(3′-(3-((ls,4s)-4-aminocyclohexylcarbamoyl)-5-fluoropyridin- 2-yloxy)biphenyl-4-yl)propyl)piperazine-l-carboxylate (150 mg, 0.24 mmol) in acetonitrile (2 mL) was added pyrazolo[l,5-a]pyridine-2-carboxylic acid (38.5 mg, 0.24 mmol) and triethylamine (0.331 mL, 2.37 mmol). 1-Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (0.159 mL, 0.25 mmol) was then added and the mixture stirred at RT for 1 h. The mixture was poured into sat NaHCO3 (aq) and the organics extracted into EtOAc (x2). The extractions were combined, dried (MgSO4) and evaporated to give a residue. This was dissolved in dichlormethane (2mL) to which TFA (2mL) was added and the mixture stirred at RT for 20 min. The solvents were removed in vacuo and the residue dissolved in methanol and purified using reverse phase preparative chromatography using eluent = TFA(aq)/MeOH. The appropriate fractions were combined and evaporated to give a residue which on trituration with ether gave a solid. The solid was dried overnight under vacuum at 40 0C to give the title compound. Yield: 58 mg1H NMR (400 MHz, CD3OD) delta 8.49 (d, J= 7.2 Hz, IH), 8.41 (d, J= 6.9 Hz, IH), 8.12 (d, J = 3.1 Hz, IH), 8.07 (dd, J= 7.9, 3.1 Hz, IH), 7.66 (d, J= 9.0 Hz, IH), 7.50 – 7.45 (m, 4H), 7.42 – 7.41 (m, IH), 7.25 – 7.20 (m, IH), 7.18 – 7.13 (m, 3H), 6.96 – 6.92 (m, 2H), 4.17 – 4.12 (m, IH), 4.04 – 3.98 (m, IH), 3.41 (t, J= 5.4 Hz, 4H), 3.24 – 3.19 (m, 4H), 2.94 – 2.89 (m, 2H), 2.64 (t, J= 7.6 Hz, 2H), 1.99 – 1.68 (m, 10H). MS: [M+H]+=676 (calc=676) (MultiMode+)

The synthetic route of 63237-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63237-88-7 , The common heterocyclic compound, 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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.

Example 132N-((ls,4s)-4-(5-fluoro-2-(4′-(3-(piperazin-l-yl)propyl)biphenyl-3- yloxy)nicotinamido)cyclohexyl)pyrazolo [ 1 ,5-a] pyridine-2-carboxamide To a solution of tert-butyl 4-(3-(3′-(3-((ls,4s)-4-aminocyclohexylcarbamoyl)-5-fluoropyridin- 2-yloxy)biphenyl-4-yl)propyl)piperazine-l-carboxylate (150 mg, 0.24 mmol) in acetonitrile (2 mL) was added pyrazolo[l,5-a]pyridine-2-carboxylic acid (38.5 mg, 0.24 mmol) and triethylamine (0.331 mL, 2.37 mmol). 1-Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (0.159 mL, 0.25 mmol) was then added and the mixture stirred at RT for 1 h. The mixture was poured into sat NaHCO3 (aq) and the organics extracted into EtOAc (x2). The extractions were combined, dried (MgSO4) and evaporated to give a residue. This was dissolved in dichlormethane (2mL) to which TFA (2mL) was added and the mixture stirred at RT for 20 min. The solvents were removed in vacuo and the residue dissolved in methanol and purified using reverse phase preparative chromatography using eluent = TFA(aq)/MeOH. The appropriate fractions were combined and evaporated to give a residue which on trituration with ether gave a solid. The solid was dried overnight under vacuum at 40 0C to give the title compound. Yield: 58 mg1H NMR (400 MHz, CD3OD) delta 8.49 (d, J= 7.2 Hz, IH), 8.41 (d, J= 6.9 Hz, IH), 8.12 (d, J = 3.1 Hz, IH), 8.07 (dd, J= 7.9, 3.1 Hz, IH), 7.66 (d, J= 9.0 Hz, IH), 7.50 – 7.45 (m, 4H), 7.42 – 7.41 (m, IH), 7.25 – 7.20 (m, IH), 7.18 – 7.13 (m, 3H), 6.96 – 6.92 (m, 2H), 4.17 – 4.12 (m, IH), 4.04 – 3.98 (m, IH), 3.41 (t, J= 5.4 Hz, 4H), 3.24 – 3.19 (m, 4H), 2.94 – 2.89 (m, 2H), 2.64 (t, J= 7.6 Hz, 2H), 1.99 – 1.68 (m, 10H). MS: [M+H]+=676 (calc=676) (MultiMode+)

The synthetic route of 63237-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem