Category: pyridine-derivatives

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. 1003-73-2, name is 3-Methylpyridine 1-oxide, molecular formula is C6H7NO, 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. Recommanded Product: 1003-73-2

Example 1; A. 3-Methyl-isonicotinonitrile.; To 3-methyl-pyridine 1 -oxide (15.90 g, 150 mmol) is added at 0 0C during 30 min. dimethylsulfate (15.60 mL). The resulting reaction mixture is stirred overnight at 40 0C. A solution of KCN (10.75 g, 165 mmol) in a mixture of EtOH/water 1 : 1 (120 mL) is added and the reaction mixture is stirred overnight at 40 0C. The reaction mixture is concentrated in vacuo and the residue is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc and the combined organic layers are dried over Na2SO4, filtered and concentrated at reduced pressure. Purification by flash column chromatography (silica gel, cyclohexane / EtOAc 85 : 15) affords the title compound as orange crystals (6.00 g, 50.80 mmol, 34%). 1H NMR (400 MHz, DMSO-(Z6) delta ppm 8.76 (s, 1 H), 8.64 (d, J = 4.9 Hz, 1 H), 7.80 (d, J = 4.9 Hz, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 1003-73-2.

Reference:
Patent; NOVARTIS AG; WO2008/122615; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76041-73-1, 3-Bromo-5-(trifluoromethyl)pyridin-2-ol, 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, Quality Control of 3-Bromo-5-(trifluoromethyl)pyridin-2-ol, blongs to pyridine-derivatives compound. Quality Control of 3-Bromo-5-(trifluoromethyl)pyridin-2-ol

A mixture of 3-bromo-5-(trifluoromethyl)pyridin-2-ol (37.75g, 0.16 mol) and phosphorus(lll) oxychloride (POCI3; 75 mL) is stirred at 1000C for 5 hours. After cooling to room temperature, the mixture is poured into ice-water, and extracted with CH2CI2 twice. The combined organic layer is washed with NaHCO3 aq., brine, dried over MgSO4, filtered and concentrated in vacuo. The crude mixture is purified by flash column chromatography to give 3-bromo-2-chloro-5-trifluoromethylpyridine (31.90 g, 79 % yield) as a white solid. 1H-NMR (400MHz, CDCI3), delta (ppm): 8.17 (m, 1H), 8.62 (d, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76041-73-1, 3-Bromo-5-(trifluoromethyl)pyridin-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/73934; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 107504-07-4, Adding some certain compound to certain chemical reactions, such as: 107504-07-4, name is Methyl 5-fluoropicolinate,molecular formula is C7H6FNO2, 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 107504-07-4.

To a mixture of (2,6-difluoro-4-iodophenyl)methanol (3 g) and THF (30 ml) was added sodium hydride (60% in oil, 444 mg) at 30C.The mixture was stirred at 30C for 30 min, and methyl 5-fluoropyridine-2-carboxylate (2.06 g) was added thereto. The mixture was stirred at 30C for 2 hr. To the mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (2.4 g). 1H NMR (400 MHz, CDCl3) delta 3.98 (3H, s), 5.17 (2H, s), 7.30-7.45 (3H, m), 8.12 (1H, d, J = 8.8 Hz), 8.43 (1H, d, J = 2.8 Hz).

According to the analysis of related databases, 107504-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIZOJIRI, Ryo; ASANO, Moriteru; TOMITA, Daisuke; BANNO, Hiroshi; TAWADA, Michiko; NII, Noriyuki; GIPSON, Krista E.; MAEZAKI, Hironobu; TSUCHIYA, Shuntaro; IMAI, Mayumi; AMANO, Yuichiro; (100 pag.)EP3279183; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 504-29-0, 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. 504-29-0, name is Pyridin-2-amine, molecular formula is C5H6N2, 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.

2-Aminopyridine (3.1g, 33mmol) and triethylamine(6.9mL, 49mmol) was dissolved in dichloromethane (40mL), 2,2-dimethylpropionyl chloride (4.5mL, 36mmol) was added on an ice bath, and the solution was stirred for 2 hours at the same temperature. Water was added thereto for extraction, the organic layer was sequentially washed with an aqueous solution of saturated sodium bicarbonate and brine, then, dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, and the title compound (6.0g, 34mmol, 102%) was obtained as a white solid. 1H-NMR Spectrum (CDCl3) delta(ppm) :1.27 (9H, s), 7.03 (1H, ddd, J=1.1, 4.9, 7.3Hz), 7.68-7.72 (1 H, m), 8.02 (1 H, s), 8.23-8.27 (2H, m).

According to the analysis of related databases, 504-29-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1052714-46-1, 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.1052714-46-1, name is 6-Bromo-5-fluoropicolinic acid, molecular formula is C6H3BrFNO2, molecular weight is 219.9959, as common compound, the synthetic route is as follows.

To a solution of 6-bromo-5-fluoropicolinic acid (1.0 equiv.) in methanol (0.2 M) was added H2SO4 (4.2 equiv.) and the reaction was stirred at room temperature for two hours. Upon completion of the reaction as monitored by LC/MS, the reaction was diluted with ethyl acetate and quenched slowly with saturated aqueous NaHCO3. The reaction was poured into a separatory funnel and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate, filtered, and concentrated in vacuo to provide methyl 6-bromo-5-fluoropicolinate as a white solid (>99%). LC/MS=233.9/235.9 (M+H), Rt=0.69 min.

The chemical industry reduces the impact on the environment during synthesis 1052714-46-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Burger, Matthew; Nishiguchi, Gisele; Machajewski, Timothy D.; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225062; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 56622-54-9, 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.56622-54-9, name is (6-Methylpyridin-3-yl)methanamine, molecular formula is C7H10N2, molecular weight is 122.17, as common compound, the synthetic route is as follows.

2-Fluoro-N-((6-methylpyridin-3-yl)methyl)-9H-purin-6-amineTo a stirred solution of 6-chloro-2-fluoropurine ( 0.4g, 2.3 mmol) in n-BuOH (50 ml) under an argon atmosphere at O0C, was added DIEA (2.5 ml, 14.7 mmol) followed by (6-methylpyridin-3-yl)methanamine (0.36g, 2.95 mmol). The reaction mixture was stirred at this temperature for 1 h and then allowed to return to room temperature and stirred for 4h, it was still seen incomplete, hence heated the reaction to 1000C and left at that temperature for 8h. The solvent was evaporated in vacuo and the residue was purified by gradient column chromatography on silica gel, eluted with CHCl3 :MeOH (100:0 ? 90:10), to afford the product as a white solid; Yield: 0.38 g (65%) deltaH CDCl3, 250 MHz) 2.44 ( 3 H, s, CH3), 3.66 – 3.57 ( 2 H, m, NHCH2), 4.63 ( 1 H, s, br, NH),7.25 ( 1 H, d, J 7.5, ArH), 7.71 (1 H, dd, J 2.5, 7.5, ArH), 8.14 ( 1 H, s, ArH), 8.49 (1 H, s, ArH), 9.07 (1 H, s, br, NH); deltac ( CDCl3, 250 MHz) 159.12 (C), 158.62 (C), 157.61 (C), 155.56 (C), 147.44 (CH), 146.99 (CH), 136.32 (C), 123.05 (2 x CH), 119.42 (C), 41.64 (CH2), 18.47 (CH3); m/z 259.2 (M + H)

Statistics shows that 56622-54-9 is playing an increasingly important role. we look forward to future research findings about (6-Methylpyridin-3-yl)methanamine.

Reference:
Patent; CYCLACEL LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; WO2008/122767; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 18437-58-6, 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 18437-58-6, name is 4-Amino-2-picoline. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of Intermediate 83B (10 mg, 0.016 mmol) in THF (1 mL) was added2-methylpyridin-4-amine (5.35 mg, 0.049 mmol) and DIEA (0.029 mL, 0.165 mmol) inDCM (1 mL). The mixture was stirred at room temperature for 2 h. TBAF (0.165 mL, 0.165 mmol) was added and the mixture was stirred at room temperature overnight. The reaction was quenched by addition of a small amount of MeOH/water/0. 1% TFA (HPLC solvent). Solvent was removed under vacuum. The residual was dissolved in DMSO andpurified via preparative LC/MS (method D, 30-70% B over 20 mm., then a 5-mm hold at100% B). Fractions containing the desired product were combined and dried via centrifugal evaporation to give Example 85 (0.8 mg, 1.420 imol, 8.60 % yield). ?H NMR (500MHz, DMSO-d6) 8.81 (s, 1H), 8.75 (d, J=1.7 Hz, 1H), 8.35 (d, J5.8 Hz, 1H), 7.95 (s, 1H), 7.50-7.39 (m, 2H), 7.15 (d, J=11.0 Hz, 1H), 5.65 (br. s., 1H), 4.83 (d, J3.6 Hz,2H), 4.71 (br. s., 1H), 4.64 (dd, J=1 1.6, 2.2 Hz, 1H), 4.57-4.44 (m, 2H), 4.31 (dd, J1 1.6,7.2 Hz, 1H), 4.10 (s, 3H), 2.46 (s, 3H). LC-MS: method C, RT = 1.48 mm, MS (ESI) m/z: 564.10 (M+H). Analytical HPLC purity (method B): 100%.

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 18437-58-6, 4-Amino-2-picoline.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; JIANG, Wen; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (545 pag.)WO2018/13776; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16498-81-0, 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. 16498-81-0, name is 2-Methoxynicotinic acid, molecular formula is C7H7NO3, 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.

2-Methoxy-3-pyridinecarboxylic acid (0.028 mol) was dissolved in DCM (150 ml). Thionyl chloride (8.2 ml; 0.112 mol)) was added dropwise to this mixture and the mixture was refluxed for 2 hours and 30 minutes. The solvent was evaporated. Then DCM (150 ml) was added and the solvent was evaporated again. The crude compound was dissolved in DCM (150 ml). First l-(phenylmethyl)-3-pyrrolidinamine (0.028 mol) was added and then a saturated aqueous NaHCCb solution (75 ml) was added. The mixture was reacted for 2 hours. Then, the layers were separated. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography (eluent: from 100 % CH2Cl2 till CH3OH/CH2C12 1/100). The product fractions were collected and the solvent was evaporated, yielding 7.97 g of intermediate (23); 2-Methoxy-3-pyridinecarboxylic acid (0.028 mol) was dissolved in DCM (150 ml). Thionyl cloride (8 ml; 0.112 mol) was added dropwise to this mixture and the mixture was refluxed for 2 hours and 30 minutes. The solvent was evaporated. Then DCM (150 ml) was added and the solvent was evaporated again. The crude compound was dissolved in DCM (150 ml). First N-methyl-N-(phenylmethyl)-l,3-propanediamine (0.028 mol) was added and then a saturated aqueous nuaHCtheta3 solution (75 ml) was added. The mixture was reacted for 2 hours. Then, the layers were separated. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography (eluent: from 100 % CH2Cl2 till CH3OH/CH2C12 1/100). The product fractions were collected and the solvent was evaporated, yielding 8.7 Ig of intermediate (27); -Methoxy-3-pyridinecarboxylic acid (0.00485 mol) was dissolved in DCM (50 ml). Thionyl chloride (1.4 ml) was added dropwise to this mixture and the mixture was refluxed for 2 hours and 30 minutes. The solvent was evaporated. Then DCM (50 ml) was added and the solvent was evaporated again. The crude compound was dissolved in DCM (50 ml). First 4-(phenylmethyl)-2-morpholinemethanamine (0.00485 mol) was added and then a saturated aqueous NaHCO3 solution (25 ml) was added. The mixture was reacted for 2 hours. Then, the layers were separated. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography (eluent : from 100 % CH2Cl2 till CH3OH/CH2C12 1/100). The product fractions were collected and the solvent was evaporated, yielding 1.6 g of intermediate (29); 2-Methoxy-3-pyridinecarboxylic acid (0.0269 mol) was dissolved in DCM (150 ml). Thionyl chloride (8 ml) was added dropwise to this mixture and the mixture was refluxed for 2 hours and 30 minutes. The solvent was evaporated. Then DCM (150 ml) was added and the solvent was evaporated again. The crude compound was dissolved in DCM (150 ml). First 4-aminohexahydro-lH-azepine-l-carboxylic acid, ethyl ester (0.0269 mol) was added and then a saturated aqueous NaetaCtheta3 solution (75 ml) was added. The mixture was reacted for 2 hours. Then, the layers were separated. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography (eluent: from 100 % CH2CL) till CH3OH/CH2Cl2 1/100). The product fractions were collected and the solvent was evaporated, yielding 8.63 of intermediate (31).

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 16498-81-0, 2-Methoxynicotinic acid.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2008/49808; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 193902-78-2, Adding some certain compound to certain chemical reactions, such as: 193902-78-2, name is tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate,molecular formula is C14H20N4O4, 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 193902-78-2.

309. Step 2: /V-(5-nitropyridin-2-yl)piperazine (B-3)To compound B-2 (19.45 g, 0.0631 mol) dissolved in CH2CI2 (250 ml_) and cooled to 0 0C was added trifluoroacetic acid (50 ml_). The resulting reaction mixture was stirred at RT for 16 h then concentrated. The crude product was dissolved in CH2CI2 (250 ml_) and made basic with the addition of 1 N aqueous NaOH (200 ml_) and 3 N aqueous NaOH (100 ml_). The layers were separated, and the aqueous solution extracted with CH2CI2. The combined organic extract was dried (MgSO4), filtered, and concentrated to give the product N-(2-fluorophenyl)-4-(5-nitropyridin-2-yl)piperazine-1-carboxamide (B- 3) as a yellow solid (13.13 g, 100% yield). MS (M+1): 209

According to the analysis of related databases, 193902-78-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; TING, Pauline, C.; ASLANIAN, Robert, G.; CAPLEN, Mary Ann; CAO, Jianhua; KIM, David, Won-Shik; KIM, Hyunjin; KUANG, Rongze; LEE, Joe, F.; SCHWERDT, John, H.; WU, Heping; ZHOU, Gang; ZORN, Nicolas; WO2010/59606; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.20265-38-7, name is 2-Methoxypyridin-3-amine, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.Quality Control of 2-Methoxypyridin-3-amine

Step 1-Synthesis of 6-chloro-N-(2-methoxypyridin-3-yl)pyrimidin-4-amineTo a solution of 4,6-dichloropyrimidine (660.04 mg, 4.43 mmol) in 1-butanol (10 mL) was added DIPEA (0.67 ml, 4.03 mmol) followed by 2-methoxypyridin-3-amine (500 mg, 4.03 mmol).The reaction mixture was then heated to 90° C. for 2 hr.The reaction mixture was then concentrated in vacuo and partitioned between DCM and water.A precipitate was removed by filtration and the organics extracted (2*20 ml DCM).The combined organic extracts were then washed with 0.5M HCl (5 ml) and then dried (Na2SO4), filtered and concentrated in vacuo to give the title intermediate (300 mg, LC-MS purity=83percent); LC-MS: m/z=+236.95/238.90 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20265-38-7, 2-Methoxypyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem