Tag: M.W:100-200

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.251101-36-7, name is 3-Methylisonicotinamide, molecular formula is C7H8N2O, molecular weight is 136.15, as common compound, the synthetic route is as follows.HPLC of Formula: C7H8N2O

3-Methyl-4-cyanopyridine (123) Phosphorus oxychloride (100 mL, 1.1 mol) was slowly added to the crude amide 122 (15 g, 0.11 mol) while cooling the mixture in an ice bath. The resulting solution was heated at reflux for 24 h. The reaction mixture was cooled to room temperature and the excess phosphorus oxychloride was removed under reduced pressure. Crushed ice (150 g) was slowly added to the oily residue, and the solution was neutralized with saturated ammonium hydroxide. The crude product was extracted with chloroform (3*100 mL). The combined extracts were filtered through a layer of silica gel, washing with extra portions of chloroform. The filtrates were evaporated to dryness to yield 123 as colorless crystals (12 g, 90%): mp 45-47 C. (lit. (J. Med. Chem. 2000, 43, 3168-3185) mp 50 C.). 1H NMR (300 MHz, CDCl3) delta 8.66 (s, 1H), 8.59 (d, J=5.0 Hz, 1H), 7.45 (d, J=5.0 Hz, 1H), 2.54 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,251101-36-7, 3-Methylisonicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; CUSHMAN, Mark S.; KISELEV, Evgeny A.; MORRELL, Andrew E.; US2014/18360; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1443759-42-9, 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 1443759-42-9 as follows.

36.3: 4-Bromo-6-methoxy-pyridine-2-carboxylic acid methyl ester To a mixture of 3.47 mL (29.3 mmol) tert-butyl nitrite and 6.60 g (29.3 mmol) copper(II)bromide in 120 mL acetonitrile was added a solution of 3.33 g (18.3 mmol) 4-amino- 6-methoxy-pyridine-2-carboxylic acid methyl ester in 30 mL acetonitrile dropwise at 40 C. This mixture was stirred at 80 C for 1 h, then poured into ice water. The precipitate was filtered off, washed with water and dried. The crude material was purified by flash chromatography (PE/EtOAc = 4/1 -> 3/1). yield: 2.50 g (56 %) + ESI-MS: m/z = 246 (M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1443759-42-9, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEIMANN, Annekatrin; DAHMANN, Georg; GRUNDL, Marc; MUELLER, Stephan Georg; WELLENZOHN, Bernd; WO2013/87805; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 145255-19-2, 5-Aminopyridine-2-carboxamide, 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, Application In Synthesis of 5-Aminopyridine-2-carboxamide, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Aminopyridine-2-carboxamide

EXAMPLE 238: 4-[4-(6-CarbamoyIpyridin-3-ylamino)-7No.-pyrrolo[2,3-rf]pyriraidin-6-yl]-3,6-dihydro-2JHr-pyridme-l-carboxylic acid tert-butyl ester; .NH2^»[673] Into the DMF (ImL) solution of 4-(4-chloro-7No.-pyrrolo[2,3-J]pyrimidin-6-yl)-3,6-dihydro-2/ir-pyridine-l-carboxylic acid tert-butyl ester (122mg, 0.363mmol) wasadded t-BuOK (1M in ^-BuOH, 0.726mL, 0.726mmol) dropwise at RT under N2 over 5min.The mixture was then put in an ice/water bath and stirred for lOmin. After that time, theDMF (ImL) solution of 5-aminopyridine-2-carboxylic acid amide (99.5mg, 0.726mmol) wasadded into the above mixture dropwise. The reaction mixture was warmed to RT.Pd2(dba)3-CHCl3 (9.4mg, 2.5%eq.) and^(+)-BINAP (22.6mg, O.leq.) were added, and themixture was heated at 100C for 24h. The mixture was filtered and the filtrate wasconcentrated in vacua. The crude was submitted to MS directed purification. A brown oilwas obtained that was purified further by HPLC to obtain the title compound as an off-whitesolid. ‘H NMR (DMSO-dft 400 MHz): 5 = 1.50 (s, 9 H), 2.50 (m, 2 H), 3.64 (t, 2 H, J= 5.6Hz), 4.12 (bra, 2 H), 6.50 (bra, 1 H), 6.88 (s, 1 H), 7.53 (d, 1 H, J= 4.2 Hz), 8.04 – 8.05 (m, 1H), 8.08 (d, 1 H, J= 8.8 Hz), 8.44 (s, 1 H), 8.68 (dd, 1 H, /= 2.4 & 8.4 Hz), 9.12 (d, 1 H, J=2.4 Hz), 9.91 (s, 1 H), 12.18 (s, 1 H). MS (ES+): m/z 436.10 (100) [MET]. HPLC: fe = 2.75min (ZQ2000, polar_5 min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,145255-19-2, 5-Aminopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58602-02-1, 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. 58602-02-1, name is 2,6-Difluoro-3-nitropyridine, molecular formula is C5H2F2N2O2, 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.

b 2-(Ethylamino)-6-fluoro-3-nitropyridine To a solution of 2,6-difluoro-3-nitropyridine (45.7 g, 285 mmol) in THF (500 mL) at -40 C. was added drop-wise a solution of ethylamine (25.7 g, 570 mmol) in THF (250 mL). After 30 min, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated. The resulting yellow solid was purified by flash chromatography (15% EtOAc in hexane) to give the title compound (43.2 g, 82% yield) as a yellow solid.

According to the analysis of related databases, 58602-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Simoneau, Bruno; US2002/28807; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89466-17-1, 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 89466-17-1, name is 6-Bromo-5-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 0.052 g ammonium chloride (1 mmol) in 4 mL water or methanol was added isocyanide (1.2 mmol), aromatic aldehyde (1.1 mmol), and 2-aminopyridine (1 mmol) and sealed in stainless steel autoclave with a Teflon-coated, and then the autoclave was put in the oven at 75oC in 2 h. The autoclave was taken out and cooled to room temperature. The reaction mixture was put into 30 mL cooled water to afford the product as a precipitate. The solid residue was filtered and crystallized from ethyl acetate to give products.

According to the analysis of related databases, 89466-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Xiaohui; Shang, Qianqian; Bo, Caiying; Hu, Lihong; Zhou, Yonghong; Arkivoc; vol. 2018; 5; (2018); p. 184 – 193;,
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.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5F3N2O

General procedure: N,N-Dimethylformamide (2 mL), triethylamine (0.079 mL, 0.57 mmol) and 1- [bis(dimethylamino)methylene]-lH-l,2,3-triazolo[4,5-]pyridinium 3-oxid hexafluorophosphate (79 mg, 0.208 mmol, HATU) were added to a mixture of the product of Example 18A (59.4 mg, 0.189 mmol) and (5-(difluoromethoxy)pyridin-2-yl)methanamine (Enamine, 33 mg, 0.189 mmol) in sequential order. The reaction mixture was then stirred at ambient temperature for 30 minutes. The resulting solution was filtered through a glass microfiber frit and purified by preparative HPLC [YMC TriArt CI 8 Hybrid 5 mupiiota column, 50 x 100 mm, flow rate 90 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (56 mg, 0.119 mmol, 63% yield). JH NMR (501 MHz, DMSO-de) delta ppm 8.73 (s, 1H), 8.44 (t, J = 6.1 Hz, 1H), 8.40 (d, J = 2.8 Hz, 1H), 7.64 (dd, J = 8.6, 2.9 Hz, 1H), 7.50 (t, J = 8.9 Hz, 1H), 7.29 (dd, J = 8.6, 0.7 Hz, 1H), 7.27 (t, J = 73.5 Hz, 1H), 7.08 (dd, J = 11.4, 2.9 Hz, 1H), 6.86 (ddd, J = 8.9, 2.9, 1.2 Hz, 1H), 4.47 (s, 2H), 4.33 (d, J = 6.1 Hz, 2H), 2.22 (s, 6H); MS (ESI+) m/z 470 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 105166-53-8, [2,2′-Bipyridin]-3-amine, 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, Product Details of 105166-53-8, blongs to pyridine-derivatives compound. Product Details of 105166-53-8

General procedure: Trifluoroacetic acid (0.75 mL, 0.009 mol) was added to a cooled (0 C) solution (4.5 mL CH2Cl2) of3-amino-2,2?-bipyridine (0.513 g, 0.003 mol), followed by isoamyl nitrite (0.61 mL, 0.004 mol). After 1 h,the diazonium salt of 3-amino-2,2?-bipyridine was precipitated out by cooling the reaction mixtureto -78 C, followed by the addition of diethyl ether (30 mL). The precipitate was filtered. A sample(2 mmol; 0.27 g) of indol-2-one was dissolved in dilute potassium hydroxide solution (15 mL) andcooled in a saltice bath and then cold diazonium solution was added to this cooled solution portionwise by stirring. The solution was further stirred at 0-5 C for 1 h. The pH of the reaction mixturewas maintained at 4-6 by the addition of solid sodium acetate in portions. The mixture was stirredfor 24 h at room temperature. The resulting solid was filtered, washed with cold water, and air-dried.Crystallization from ethanol gave yellow crystalline.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105166-53-8, [2,2′-Bipyridin]-3-amine, and friends who are interested can also refer to it.

Reference:
Article; ?andrik, Robert; Tisovsky, Pavol; Csicsai, Klaudia; Donovalova, Jana; Gaplovsky, Martin; Sokolik, Robert; Filo, Juraj; Gaplovsky, Anton; Molecules; vol. 24; 14; (2019);,
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.6854-07-5, name is 5-Nitro-2-oxo-3-pyridinecarboxylic Acid, molecular formula is C6H4N2O5, molecular weight is 184.11, as common compound, the synthetic route is as follows.Recommanded Product: 6854-07-5

Step B 2-Methoxy-3-carbomethoxy-5-nitropyridine 2-Hydroxy-3-carboxy-5-nitropyridine was converted to 2-chloro-3-chlorocarbonyl-5-nitropyridine in situ and converted to the title compound by reaction with anhydrous methanol according to the procedure of A. Monge et al J. Het. Chem. (29), 1545 (1992). In a 500 mL was added starting material (10.2 g, 54 mmol) in 200 mL of chlorobenzene.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6854-07-5, 5-Nitro-2-oxo-3-pyridinecarboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US5750549; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6854-07-5, Adding some certain compound to certain chemical reactions, such as: 6854-07-5, name is 5-Nitro-2-oxo-3-pyridinecarboxylic Acid,molecular formula is C6H4N2O5, 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 6854-07-5.

A suspension of Part A(l) compound (7.0 g, 38 mmol) in phosphorus oxychloride (20 mL) was heated at reflux for 2 h, cooled to RT, and added slowly to H2O (100 mL) with stirring, maintaining the temperature below 40’C with added ice. Following addition, the mixture was stirred at RT for 30 min, whereupon a precipitate formed. The mixture was extracted with Et2O/THF (2:1, 2 x 200 mL), and the combined organic extracts were washed with brine (100 mL), dried over Na2SO4, and concentrated to give an oily yellow solid. The crude product was taken up in hot Et2O/hexane (1:1, 200 mL), filtered, and the filtrate was concentrated to give title compound (5.78 g, 75%) as a yellow solid (mp 140-141C, lit mp 142-143C).

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. 6854-07-5, 5-Nitro-2-oxo-3-pyridinecarboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EP904262; (2004); B1;,
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.1802-20-6, name is 3-Pentylpyridine, molecular formula is C10H15N, molecular weight is 149.23, as common compound, the synthetic route is as follows.Recommanded Product: 1802-20-6

1,12-Dibromododecane (0.20 g, 0.61 mmol) was dissolved in 4-methyl-2- pentanone (2.0 ml) and 3-pentylpyridine (0.20 g, 1.34 mmol) was added. The mixture was 5 stirred at reflux for 20 h under a nitrogen atmosphere, and the solvent was removed under reduced pressure. The crude was triturated with Et2O (8 x 10 ml), and the solvent was removed under reduced pressure. The residue was purified by Al2O3 chromatography (neutral, activity H-III)5 using gradient elution (starting with CHCl3/MeOH = 2 % to 10 %). The residue was passed down a column of Lewatit MP-64 anion resin (Cl”), eluting with EtOH. The resulting fractions were combined and the solvent removed under reduced pressure to give the above compound as a light yellow waxy oil (0.28 g, 85 %).5 1H NMR (300 MHz, CDCl3): delta 9.55 (4H, m, CH(2′,6′)), 8.20 (2H, d, J= 6.5 Hz, CH(4′)), 8.07 (2H3 m, CH(3′)), 5.00 (4H5 m5 CH2(I)), 3.10 (4H5 m, CH2(I”)), 2.89 (4H5 m, CH2(2″))5 2.06 (4H5 m5 CH2(2))5 1.72 (4H5 m5 CH2(3″))5 1.33 (12H5 m, CH2(354,4″)), 1.33 (8H5 m, CH2(5,6)), 0.96 (6H, m, CH3(5″)). 13C NMR (300 MHz, CDCl3): 164.2, 144.2, 128.5, 61.2, 35.6, 32.2, 31.4, 29.5, 29.4, 29.1, 26.2, 22.4, 13.3, 1 signal obscured or io overlapping. MS: m/z ESI (positive ion) 233 [M-2C1″]2+ (18 %), 465 [M-2Cl”-H+]+ (10). Found [M-2C1″]2+ 233.2136, [C16H27N]2+ requires 233.2144.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1802-20-6, 3-Pentylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF SYDNEY; WO2007/128059; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem