Category: 33252-28-7

Application of 33252-28-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, molecular weight is 138.55, as common compound, the synthetic route is as follows.

A mixture of [1,] [2-DIAMINO-2-METHYLPROPANE] [(3.] 14ml, [30] [MMOL),] and 6- chloronicotinonitrile [(2.] [77G,] [20] mmol) were heated to [120 C] for 2 days. The reaction mixture was filtered, and the inorganic salt was rinsed with EtOAc. The filtrate was concentrated under reduced pressure to provide the titled compound as a pale yellow solid. MS [(DCI)] [191] 1 9 1 [(M+H)] [+.]

The chemical industry reduces the impact on the environment during synthesis 33252-28-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/26822; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 33252-28-7, name is 6-Chloronicotinonitrile, the common compound, a new synthetic route is introduced below. Formula: C6H3ClN2

A 185 ml stirred autoclave was charged under argon with PdC12(dppp) (213 mg, 0.36 1 mmol), 6- chloro-nicotinonitrile (10 g, 72.2 mmol), dioxane (50 ml), deionized water (50 ml) and sodium, bicarbonate (15.2 g, 0.18 mol, 2.5 molar equivalents). The reaction vessel was closed, purged three times with carbon monoxide (15 bar) and finally charged with carbon monoxide to 60 bar. The mixture was stirred vigorously at 60C under constant pressure for 22 h; after this time no more carbon monoxide absorption was observed. The reaction mixture was transferred to a5 round-bottomed flask with aid of water and, after having removed the organic volatilecomponents on a rotary evaporator, the reaction mixture was worked-up as reported in Example1. Crystallization afforded 5-cyano-pyridine-2-carboxylic acid (9.55 g) as a white solid with 99.6a% purity by HPLC.Example 5a-h5-Cyano-pyridine-2-carboxylic acid A series of reaction conditions was tested using the same procedure described in Example 4. The results are included in the following table.Ex.PbarTCBase ImolarequivalentsSolvent Ivol/volratio2-Cl,5-CN-Py[a%]3-CN-Py-2-C0211[a % I3-CN-Py[a%]Isol.Yield(%)5a6060Na2CO31.25Water 1Dioxane 10.293.51.6895b6060NaOAc2.5Water 1Acetone 13.683.57.9n.d.5c4060Et3N2.5Water 1 t-BuOH 10.795.91.0895d1560Et3N2.5Water 1t-BuOH 4<0.195.41.992Se70100Et3N2.2Water 1THF40.453.825n.d.Sf3580Et3N2.5Water 1 CH3CN 4<0.193.54.9n.d.Sg3580Et3N2.5Water 1CH3CN 4MeOH 1<0.191.51.5n.d.5h4050Et3N2.5Water 1t-BuOH 110.586.60.5n.d.Example no. Sc: reaction time S h; example no. Sd and Sh: reaction time 16 h; example no. Sf:reaction time 12 h.Examples no. Se and Sf: S g of 2-Cl,S-CN-Py, S/C 330.Example no. Sg: crude mixture contains 3.7 a% of the methyl ester 3-CN-Py-2-CO2Me. a% S values are obtained by HPLC analysis. The synthetic route of 33252-28-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FETTES, Alec; MARTY, Hans-Peter; SCALONE, Michelangelo; WO2014/173917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 33252-28-7, name is 6-Chloronicotinonitrile, the common compound, a new synthetic route is introduced below. name: 6-Chloronicotinonitrile

To a mixture of 6-chloropyridine-3-carbonitrile (10 g, 0.06 mol) and (2R)-2-methylpiperazine(6.35 g, 0.06 mol) in acetonitrile (80 mL), K2C03 (12.0 g, 0.09 mol) was added at RT. Theresulting mixture was stirred at 60C for 2 h (TLC indicated complete consumption ofstarting material). The reaction was brought toRT, quenched with water (150 mL) andextracted with EtOAc (3 x 80 mL). The combined organic extracts were dried over anhydrousNa2S04 and concentrated under reduced pressure. The residue was purified by columnchromatography (100-200 silica gel, 5% MeOH-DCM) to afford 6-[(3R)-3-methylpiperazine-1-yl]-pyridine-3-carbonitrile (10.0 g, 69% yield).

The synthetic route of 33252-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile. A new synthetic method of this compound is introduced below.

2-Chloro-5-cyanopyridine (1 .5 g) is dissolved in hydrazine (6 mL) at r.t. and an exothermic reaction occurs and a solid precipitate forms. Water is added and the solid is filtered off washing with water and is dried by suction to give the hydrazine intermediate

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33252-28-7, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/168315; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

N-[4-(5-Cyano-2-methoxy-pyridin-3-yl)-benzyl]-2-trifluoromethoxy-benzenesulfonamide To a solution of 4-aminomethylphenylboronic acid hydrochloride (2.0 g, 13.2 mmol) in methanol (20 ml) was added di-tert-butyl dicarbonate (3.16 g, 15.5 mmol) and sodium bicarbonate (3.32 g, 19.8 mmol). The mixture was sonicated for 4 h then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and the solvent evaporated to give (4-bromo-benzyl)-carbamic acid tert-butyl ester (1.8 g, 13.2 mmol, 100%) as a white solid. To 6-chloro-nicotinonitrile (15 g, 0.11 mol) under argon atmosphere was added 25% sodium methoxide in methanol (11.7 g, 0.22 mol) and the mixture heated under reflux for 20 h. The methanol was evaporated and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried over anhydrous magnesium sulfate and the solvent evaporated to give 6-methoxy-nicotinonitrile (17.0 g, 0.13 mol, 117%) as a white solid. To 6-methoxy-nicotinonitrile (13.2 g, 99 mmol) in acetic acid (32 ml) was added sodium acetate (8.1 g, 99 mmol). The mixture was stirred and a solution of bromine (31.5 g, 197 mmol) in acetic acid (32 ml) added. The mixture was heated to 80 C. for 48 h. The reaction mixture was poured into water and extracted with diethyl ether. The organic phase was washed with 4M aqueous sodium hydroxide solution, 5% sodium thiosulfate solution, dried over anhydrous potassium carbonate and the solvent was evaporated to give 5-bromo-6-methoxy-nicotinonitrile (11.9 g, 56 mmol, 57%). To a solution of 2-methoxy-5-cyanopyridine-3-boronic acid (1.0 g, 4.0 mmol) in 1,2-dimethoxyethane (10 ml) was added (4-bromo-benzyl)-carbamic acid tert-butyl ester (0.42 g, 2.0 mmol), tetrakis(triphenylphosphine)palladium (0) (114 mg, 0.1 mmol) and 2M aqueous sodium carbonate (1 ml, 2.0 mmol). The reaction was heated to 150 C. for 10 min in a microwave over. The mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The organic phase was washed with water, then brine, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was purified on silica gel eluting with 5:1 heptane/ethyl acetate to give [4-(5-cyano-2-methoxy-pyridin-3-yl)-benzyl]-carbamic acid tert-butyl ester as a white solid (0.5 g, 1.47 mmol, 37%). To a solution of [4-(5-cyano-2-methoxy-pyridin-3-yl)-benzyl]-carbamic acid tert-butyl ester (0.5 g, 1.5 mmol) in dichloromethane (5 ml) at 0 C. was added trifluoroacetic acid (5 ml, 28 mmol). The reaction mixture was stirred for 30 min at 0 C. before the solvent was evaporated and the residue purified on a SCX column (eluted with 2M ammonia in methanol) to give 5-(4-aminomethyl-phenyl)-6-methoxy-nicotinonitrile as a clear glass (0.39 g, 1.6 mmol, 107%). To a solution of 5-(4-aminomethyl-phenyl)-6-methoxy-nicotinonitrile (57.3 mg, 0.24 mmol) in dichloromethane (2 ml) was added triethylamine (73.0 mg, 0.72 mmol) and 2-(trifluoromethoxy)benzenesulfonyl chloride. The reaction mixture was agitated for 20 hours and the solvent evaporated under reduced pressure. The crude product was taken up in dimethyl sulfoxide (1 ml) and purified by preparatory LCMS. The solvent was evaporated under reduced pressure to give the title compound (19.1 mg, 0.04 mmol, 17%). 1H NMR (400 MHz, DMSO-d6): delta 8.68 (d, 1H), 8.47 (t, 1H), 8.15 (d, 1H), 7.90 (m, 1H), 7.73 (m, 1H), 7.45-7.55 (m, 4H), 7.31 (d, 2H), 4.19 (d, 2H), 3.96 (s, 3H) ppm; MS (ESI) m/z: 464.3 [M+H]+.

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 33252-28-7, 6-Chloronicotinonitrile.

Reference:
Patent; N.V. Organon; Pharmacopeia Drug Discovery Inc.; US2007/149577; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, Adding some certain compound to certain chemical reactions, such as: 33252-28-7, name is 6-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 33252-28-7.

General procedure: To a 0.5 M solution of 2-chloro-5-cyanopyridine (10 mmol) in isopropyl alcohol hydrazine hydrate (50 mmol) was added in portions over 1 hour. The reaction mixture was heated at reflux for 24 hours, cooled down to ambient temperature and the resulting precipitate of 5-cyano-2-hydrazinopyridine was separated by filtration, washed with isopropyl alcohol and air-dried. Without further purification, it was dissolved in the respective aliphatic carboxylic acid (0.5M) and heated at reflux for 48 hours. Upon cooling to room temperature, the volatiles were removed in vacuo and the residue was triturated with 1M aqueous sodium bicarbonate. The precipitate thus formed was filtered off, washed with water and air dried. The resulting 1,2,4-triazolo[4,3-a]pyridine 9 was dissolved in 7M methanolic ammonia (0.25 M with respect to 9) and was hydrogenated over Raney Nickel catalyst (0.5 equiv.) at 100 atm and 60 C over 48 hours. Once it reached room temperature, the mixture was filtered through a short plug of silica gel and concentrated in vacuo. Chromatography on silica gel using 05% MeOH in CH2Cl2 afforded analytically pure compounds 8a-e.

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mishchuk, Alexander; Shtil, Natalia; Poberezhnyk, Mykola; Nazarenko, Konstiantyn; Savchenko, Timur; Tolmachev, Andrey; Krasavin, Mikhail; Tetrahedron Letters; vol. 57; 9; (2016); p. 1056 – 1059;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile. A new synthetic method of this compound is introduced below.

2-Chloro-5-cyanopyridine (1 .5 g) is dissolved in hydrazine (6 mL) at r.t. and an exothermic reaction occurs and a solid precipitate forms. Water is added and the solid is filtered off washing with water and is dried by suction to give the hydrazine intermediate

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33252-28-7, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/168315; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

N-[4-(5-Cyano-2-methoxy-pyridin-3-yl)-benzyl]-2-trifluoromethoxy-benzenesulfonamide To a solution of 4-aminomethylphenylboronic acid hydrochloride (2.0 g, 13.2 mmol) in methanol (20 ml) was added di-tert-butyl dicarbonate (3.16 g, 15.5 mmol) and sodium bicarbonate (3.32 g, 19.8 mmol). The mixture was sonicated for 4 h then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and the solvent evaporated to give (4-bromo-benzyl)-carbamic acid tert-butyl ester (1.8 g, 13.2 mmol, 100%) as a white solid. To 6-chloro-nicotinonitrile (15 g, 0.11 mol) under argon atmosphere was added 25% sodium methoxide in methanol (11.7 g, 0.22 mol) and the mixture heated under reflux for 20 h. The methanol was evaporated and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried over anhydrous magnesium sulfate and the solvent evaporated to give 6-methoxy-nicotinonitrile (17.0 g, 0.13 mol, 117%) as a white solid. To 6-methoxy-nicotinonitrile (13.2 g, 99 mmol) in acetic acid (32 ml) was added sodium acetate (8.1 g, 99 mmol). The mixture was stirred and a solution of bromine (31.5 g, 197 mmol) in acetic acid (32 ml) added. The mixture was heated to 80 C. for 48 h. The reaction mixture was poured into water and extracted with diethyl ether. The organic phase was washed with 4M aqueous sodium hydroxide solution, 5% sodium thiosulfate solution, dried over anhydrous potassium carbonate and the solvent was evaporated to give 5-bromo-6-methoxy-nicotinonitrile (11.9 g, 56 mmol, 57%). To a solution of 2-methoxy-5-cyanopyridine-3-boronic acid (1.0 g, 4.0 mmol) in 1,2-dimethoxyethane (10 ml) was added (4-bromo-benzyl)-carbamic acid tert-butyl ester (0.42 g, 2.0 mmol), tetrakis(triphenylphosphine)palladium (0) (114 mg, 0.1 mmol) and 2M aqueous sodium carbonate (1 ml, 2.0 mmol). The reaction was heated to 150 C. for 10 min in a microwave over. The mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The organic phase was washed with water, then brine, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was purified on silica gel eluting with 5:1 heptane/ethyl acetate to give [4-(5-cyano-2-methoxy-pyridin-3-yl)-benzyl]-carbamic acid tert-butyl ester as a white solid (0.5 g, 1.47 mmol, 37%). To a solution of [4-(5-cyano-2-methoxy-pyridin-3-yl)-benzyl]-carbamic acid tert-butyl ester (0.5 g, 1.5 mmol) in dichloromethane (5 ml) at 0 C. was added trifluoroacetic acid (5 ml, 28 mmol). The reaction mixture was stirred for 30 min at 0 C. before the solvent was evaporated and the residue purified on a SCX column (eluted with 2M ammonia in methanol) to give 5-(4-aminomethyl-phenyl)-6-methoxy-nicotinonitrile as a clear glass (0.39 g, 1.6 mmol, 107%). To a solution of 5-(4-aminomethyl-phenyl)-6-methoxy-nicotinonitrile (57.3 mg, 0.24 mmol) in dichloromethane (2 ml) was added triethylamine (73.0 mg, 0.72 mmol) and 2-(trifluoromethoxy)benzenesulfonyl chloride. The reaction mixture was agitated for 20 hours and the solvent evaporated under reduced pressure. The crude product was taken up in dimethyl sulfoxide (1 ml) and purified by preparatory LCMS. The solvent was evaporated under reduced pressure to give the title compound (19.1 mg, 0.04 mmol, 17%). 1H NMR (400 MHz, DMSO-d6): delta 8.68 (d, 1H), 8.47 (t, 1H), 8.15 (d, 1H), 7.90 (m, 1H), 7.73 (m, 1H), 7.45-7.55 (m, 4H), 7.31 (d, 2H), 4.19 (d, 2H), 3.96 (s, 3H) ppm; MS (ESI) m/z: 464.3 [M+H]+.

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 33252-28-7, 6-Chloronicotinonitrile.

Reference:
Patent; N.V. Organon; Pharmacopeia Drug Discovery Inc.; US2007/149577; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, Adding some certain compound to certain chemical reactions, such as: 33252-28-7, name is 6-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 33252-28-7.

General procedure: To a 0.5 M solution of 2-chloro-5-cyanopyridine (10 mmol) in isopropyl alcohol hydrazine hydrate (50 mmol) was added in portions over 1 hour. The reaction mixture was heated at reflux for 24 hours, cooled down to ambient temperature and the resulting precipitate of 5-cyano-2-hydrazinopyridine was separated by filtration, washed with isopropyl alcohol and air-dried. Without further purification, it was dissolved in the respective aliphatic carboxylic acid (0.5M) and heated at reflux for 48 hours. Upon cooling to room temperature, the volatiles were removed in vacuo and the residue was triturated with 1M aqueous sodium bicarbonate. The precipitate thus formed was filtered off, washed with water and air dried. The resulting 1,2,4-triazolo[4,3-a]pyridine 9 was dissolved in 7M methanolic ammonia (0.25 M with respect to 9) and was hydrogenated over Raney Nickel catalyst (0.5 equiv.) at 100 atm and 60 C over 48 hours. Once it reached room temperature, the mixture was filtered through a short plug of silica gel and concentrated in vacuo. Chromatography on silica gel using 05% MeOH in CH2Cl2 afforded analytically pure compounds 8a-e.

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mishchuk, Alexander; Shtil, Natalia; Poberezhnyk, Mykola; Nazarenko, Konstiantyn; Savchenko, Timur; Tolmachev, Andrey; Krasavin, Mikhail; Tetrahedron Letters; vol. 57; 9; (2016); p. 1056 – 1059;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, molecular weight is 138.55, as common compound, the synthetic route is as follows.

[N- (5-CYANO-2-PHENYL-LH-PYRROLOF2, 3-BLPYRIDIN-3-YL)-ACETAMIDE] [6-CHLORO-NICOTINONITRILE] (1.38 g, 10 mmol) was dissolved in 1,4-dioxane (50 ml). Hydrazine hydrate (0.525 ml, 10.4 mmol) was added and the resulting solution stirred for 1.5h, whereupon it was concentrated in vacuo. The residue was chromatographed (silica gel, gradient ethyl acetate/heptane from 1: 1 to 1: 0). The slower running component was concentrated in vacuo to afford the 6-hydrazino-nicotinonitrile monohydrate [0.80 g, 53%, APCI-MS m/z: 135.2 [MH+] ]. Part of this hydrazine (67 mg, 0.5 mmol) and [N- (2-OXO-2-] [PHENYL-ETHYL)-ACETAMIDE] (85 mg, 0.5 mmol) were fused together for lh at 230 [C.] The reaction mixture was allowed to cool and the glassy solid suspended in warm dichloromethane/methanol (7: 3 mixture) and then filtered. The solid was further washed with hot [ACETONITRILE/N,] [N-DIMETHYLFORMAMIDE] (9: 1 mixture) and finally acetonitrile. This afforded the title compound as a grey powder (25 mg, 18%). ‘H-NMR (DMSO-d6) : [B] 12.64 [(1H,] s); 9.66 [(1H,] s); 8.62 [(1H,] s); 8.27 (1H, s); 7.84 (2H, d); 7.52 (2H, t); 7.42 [(1H,] t); 2.10 (3H, s). [‘3C-NMR] (DMSO-d6) : [8] 147.3 ; 145.8 ; 134.0 ; 131.5 ; 129.9 ; 128.8 ; 128.7 ; 127.5 ; 118.8 ; 117.6 ; 110.1 ; 99.9 ; [22. 7.] APCI-MS m/z : 277.1 [[MH+].]

The chemical industry reduces the impact on the environment during synthesis 33252-28-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2004/16609; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem