Day: April 13, 2022

Reference of 66909-38-4, 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.66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.5862, as common compound, the synthetic route is as follows.

A mixture OF 4-(6-CHLORO-5-METHYL-PYRIMIDIN-4-YLOXY)-PIPERIDINE-1-CARBOXYLIC acid isopropyl ester (1.80 g, 5.74 mmol), palladium acetate (155 mg, 0.69 mmol), biphenyl-3-yl-di-tert-butyl- phosphane (21.5 mg, 0.072 mmol), sodium tert-butoxide (1.38 g, 14.4 mmol), and 6-CHLORO-4-METHYL- pyridin-3-ylamine (838 mg, 5.80 mmol) in 20 mL dioxane was heated in microwave for 1 hour at 120C. Solids were filtered off and mixture was purified by column chromatography (hexane/AcOEt) to give Compound A98 as a tanned solid (702 mg, 29%). H NMR (CDCL3, 400 MHz) 8 1.24-1. 26 (d, 6H), 1.72-1. 81 (M, 2H), 1.95-2. 02 (M, 2H), 2.10 (s, 3H), 2.27 (s, 3H), 3.37-3. 43 (M, 2H), 3.74-3. 77 (M, 2H), 4.90-4. 97 (m, 1H), 5.29-5. 34 (M, 1H), 5.91 (s, 1H), 7.00 (s, 1H), 8.22 (s, 1H), 8.57 (s, 1H). Exact mass calculated for C2OH26CIN503 419.17, found 420.4 (MH+).

The chemical industry reduces the impact on the environment during synthesis 66909-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153747-97-8, 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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

The compound (R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-5-(4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.89 g, 1.46 mmol)Dissolved in DME (10 mL),Then, tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (0.5 g, 1.46 mmol) was added to the reaction mixture.Cesium carbonate (1.43g, 4.38mmol),Water (2mL) andPd(dppf)Cl2.CH2Cl2 (120 mg, 0.15 mmol).After the reaction system was purged with nitrogen (nitrogen) three times,Stir at 100C overnight,Then add ethyl acetate (50 mL)Diluted the reaction solution with water (12 mL).The layers were separated, the aqueous phase was extracted with ethyl acetate (50 mL x 2), and the combined organic phases were washed with saturated brine (25 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The resulting residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether (v/v) = 1/1)The title compound was obtained as a yellow oil (0.69 g, 63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88569-83-9, 2-Methoxy-6-(methylamino)pyridine, 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, Recommanded Product: 2-Methoxy-6-(methylamino)pyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Methoxy-6-(methylamino)pyridine

Preparation 4 Ethyl 6-iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylate 6-Methoxy-N-methyl-2-pyridinamine (17.24 g, 124 mmol) is dissolved in DMF (160 mL) and cooled to 0 C. followed by the addition of NIS (28 g, 124 mmol, 1 equiv), at a rate which keeps the reaction temperature below 10 C. The reaction is then allowed to warm to room temperature and stirred for 1 h. The reaction is distilled to dryness in vacuo and the residue is dissolved in CH2Cl2 and passed through a silica plug eluding with heptane/EtOAc (9/1) affording 32 g of crude 5-iodo-6-methoxy-N-methyl-2-pyridinamine. The crude 5-iodo-6-methoxy-N-methyl-2-pyridinamine is dissolved in diethyl ethoxymethylenemalonate (32 mL) and the mixture is heated at 140 C. for 2 h, then cooled to room temperature and passed through a silica plug eluding with heptane/EtOAc (19/1, 0/1). The product is then dissolved in Eaton’s reagent (132 mL) and heated at 100 C. for 40 min, cooled to rt and poured into Na2CO3. The basic aqueous layer is then extracted with CH2Cl2 (3*), washed with water, and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (heptane/EtOAc, 4/1, 1/1, CH2Cl2/MeOH 19/1) the desired product is then triturated with MeOH to afford 7.9 g (16%) of ethyl 6-iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylate. Physical characteristics are as follows: 1H NMR (CDCl3) delta 9.04, 8.52, 4.41, 4.13, 3.91, 1.43; IR (diffuse reflectance) 2491, 2427, 2350, 2282, 2242, 1678, 1632, 1613, 1579, 1384, 1309, 1275, 1227, 1106, 804, cm-1; MS (EI) m/z 388, 344, 343, 317, 316, 185, 159, 86, 84, 51; Anal calcd for C13H13IN2O4: C, 40.23; H, 3.38; N, 7.22. Found: C, 40.20; H, 3.40; N, 7.16.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88569-83-9, 2-Methoxy-6-(methylamino)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Vaillancourt, Valerie A.; Thorarensen, Atli; US2002/19413; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17570-98-8, 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. 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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.

General procedure: 5.1.1 General procedure A (for synthesis of compounds 1-19). To 2-bromoacetylpyridine hydrobromide (1.0 equiv) in anhydrous ethanol (5 mL) was added the corresponding thiourea (1.0 equiv, 0.2 g) and the reaction mixture refluxed for 4 h. After cooling to ambient temperature the reaction mixture was poured into water. The pH of the mixture was adjusted to pH 8 with concentrated aqueous NH4OH and the mixture stirred for 2 h. The precipitate was filtered, washed with ethanol and dried to afford the title compound.

According to the analysis of related databases, 17570-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Meissner, Anja; Boshoff, Helena I.; Vasan, Mahalakshmi; Duckworth, Benjamin P.; Barry III, Clifton E.; Aldrich, Courtney C.; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6385 – 6397;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 138588-22-4, Adding some certain compound to certain chemical reactions, such as: 138588-22-4, name is 3-(Pyridin-2-yl)-1,2,4-thiadiazol-5-amine,molecular formula is C7H6N4S, 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 138588-22-4.

3-Pyridin-2-yl-[l,2,4]thiadiazo{-5-ylamine (50 mg, 0.28 mmol) was dissolved in 1 mL of anhydrous tetrahydrofuran, to which solution was added p-methoxyphenyl isocyanate (36 muEpsilon, 0.28 mmol). The mixture was stirred at 50 C overnight. Precipitation formed which was filtered and rinsed with methanol to yield a white solid (47,9 mg, 52%). NMR (400 MHz, DMSO-ifc) delta ppm 3.74 (s, 3 H) 6.81 – 7.06 (m, 2 H) 7.32 – 7.46 (m, 2 H) 7.46 – 7.57 (m, 1 H) 7.83 FontWeight=”Bold” FontSize=”10″ 8.06 (m, 1 i n 8.19 i d. ./ 7.S6 Hz, 1 H) 8.60 · 8.90 (m, 1 H) 9.12 (s, 1 I I ) 1 1.49 (s, 1 H); LCMS (M/Z): M+H ” 328.

According to the analysis of related databases, 138588-22-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCYNEXIS INC.; LIU, Hao; SLIGAR, Jessica, Marie; SPEAKE, Jason, Daniel; MOORE, Joseph, A., III; BECK, Brent, Christopher; WO2015/73797; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 4966-90-9, name is 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one, molecular formula is C6H6N2O4, 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. category: pyridine-derivatives

Part A 2,4-Dichloro-6-methyl-3-nitropyridine 4-hydroxy-6-methyl-3-nitropyridone, (18.67 g, 0.11 mol) was heated at reflux with diethylaniline (19 mL, 0.12 mol) in POCl3 (85 mL) for 3 h. After cooling it was poured into ice/water (800 mL), allowed to react for 2.5 h and extracted with EtOAc (3*400 mL). The combined organic extracts were washed with NaHCO3 (200 mL), brine (200 mL), dried (MgSO4) and stripped in vacuo. The residue was dissolved in EtOAc (100 mL) and passed through a glass funnel packed with 1 in silica gel and 1 in celite. The filtrate was stripped in vacuo to give the product. NMR (CDCl3) 7.30 (s, 1H), 2.61 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 4966-90-9.

Reference:
Patent; Dupont Pharmaceuticals Company; US6107301; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1160791-13-8, Adding some certain compound to certain chemical reactions, such as: 1160791-13-8, name is 2-Amino-6-bromothiazolo[5,4-b]pyridine,molecular formula is C6H4BrN3S, 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 1160791-13-8.

To a solution of 6-bromothiazolo[5,4-b]pyridin-2-amine IV (1.30 g, 5.55 mmol) in 1 ,4- dioxane (20.0 mL) was added ethylisocyanate (2.19 mL, 27.07 mmol) and the resulting reaction mixture was heated to 8O0C for 8 h. After the completion of the reaction (TLC monitoring), 1 ,4.-dioxane was distilled off followed by co-distillation with n-hexane (2 times). The residue was then stirred with water at 9O0C for 2h followed by filtration to obtain the desired product that was further washed with hot water and then dried. The residue was finally washed with ether to obtain the desired product (1.40 g, 83%). 1H NMR (400MHz, DMSO-d6): delta 1.10 (t, J= 7.20 Hz, 3H), 3.20 (quintet, J= 7.20 Hz, 2H), 6.76 (br s, 1 H), 8.24 (d, J= 2.0 Hz, 1 H), 8.45 (d, J= 2.0 Hz1 1 H) and 11.05 (br s, 1 H).

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. 1160791-13-8, 2-Amino-6-bromothiazolo[5,4-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROLYSIS LTD; WO2009/74812; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 290307-40-3, name is 2-(5-Bromopyridin-2-yl)propan-2-ol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 290307-40-3

In a 2 L round-bottomed flask was mixed 2,5-dibromopyridine (54 g, 228 mmol) in toluene (600 ml) to give a colorless solution. The reaction was cooled to -78 C. and n-Butyllithium 2.5M hexanes (100 ml, 251 mmol) was added at a rate that the temperature did not exceed -70 C. The reaction was stirred for 30 minutes and then acetone (20.08 ml, 274 mmol) was added quickly. The reaction was stirred for 30 minutes and then quenched with saturated ammonium chloride. The organic layer was washed with brine, dried over sodium sulfate and solvent removed under reduced pressure. The crude residue was purified by column chromatography 20-50% ethyl acetate/heptane to give 42.5 g of 2-(5-bromopyridin-2-yl)propan-2-ol in 86% yield.In a 1 L round-bottomed flask was mixed compound 2-(5-bromopyridin-2-yl)propan-2-ol (10 g, 46.3 mmol) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (11.87 g, 50.9 mmol) in dioxane (300 ml). To this was added saturated sodium bicarbonate (150 mL). The reaction mixture was degassed via purging with a stream of nitrogen and then Pd(PPh3)4 (2.67 g, 2.314 mmol) was added. The mixture was heated to reflux becoming very thick then finally going into solution. The reaction was heated for 2 hours, cooled to room temperature and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and solvent removed under reduced pressure to give 2-(5-(5-amino-2-methylphenyl)pyridin-2-yl)propan-2-ol.The crude product from above was dissolved in dioxane (30 mL) and cooled to 0 C. Sulfuric acid was added to the solution through an addition funnel with manual stirring necessary at the beginning of addition, finally going to solution. The reaction was allowed to exotherm up to 30 C. and stirred for 30 minutes. Upon completion of the reaction as determined by LC/MS, the reaction was poured onto ice, extracted with ethyl acetate (2×200 mL) and the pH of the aqueous was adjusted to 9-10 by addition of 50% sodium hydroxide solution. The mixture was then extracted with ethyl acetate, the organic was washed with brine and dried over sodium sulfate. After removal of solvent the crude product was isolated by column chromatography eluting 0-100% ethyl acetate/heptane to give 4-methyl-3-(6-(prop-1-en-2-yl)pyridin-3-yl)aniline. Yield 9 g, 86% over 2 steps.4-Methyl-3-(6-(prop-1-en-2-yl)pyridin-3-yl)aniline (9 g, 40.1 mmol) was dissolved in ethanol (100 mL) and 10% palladium on carbon (0.5 g) was added. The mixture was hydrogenated at 30 psi for 2 hours. Filtration and concentration of the product afforded clean 3-(6-isopropylpyridin-3-yl)-4-methylaniline. Yield 8 g, 88%

With the rapid development of chemical substances, we look forward to future research findings about 290307-40-3.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; US2010/41642; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1192813-41-4, Adding some certain compound to certain chemical reactions, such as: 1192813-41-4, name is 2-(Difluoromethoxy)-5-nitropyridine,molecular formula is C6H4F2N2O3, 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 1192813-41-4.

Step B: 6-(Difluoromethoxy)pyridin-3-amine To 2-(difluoromethoxy)-5-nitropyridine (4.7 g, 24.7 mmol) in degassed methanol (100 mL) was added 10% palladium on carbon (500 mg, 0.47 mmol) and the reaction was hydrogenated at atmospheric pressure for 1 hour. To this was added acetic acid (2.83 mL, 49.4 mmol) and the reaction was filtered through Celite and concentrated in vacuo to afford 6-(difluoromethoxy)pyridin-3-amine (6.33 g, 25.9 mmol, 105% yield) as an olive green liquid. 1H NMR (400 MHz, MeOD-d4) delta ppm 7.60 (d, J=2.76 Hz, 1H), 7.37 (s, 0.5H), 7.15 (dd, J=8.66, 2.89 Hz, 1H), 7.00 (s, 0.5H), 6.71 (d, J=8.78 Hz, 1H).

According to the analysis of related databases, 1192813-41-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/270405; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58481-17-7, Methyl 2-(hydroxymethyl)isonicotinate, 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, name: Methyl 2-(hydroxymethyl)isonicotinate, blongs to pyridine-derivatives compound. name: Methyl 2-(hydroxymethyl)isonicotinate

Under ice-cooling, sodium hydride (187 mg, 60%, dispersed in liquid paraffin) was added to a solution ofmethyl 2-(hydroxymethyl)isonicotinate (650 mg) in N,N-dimethyl formamide (8.0 mL), followed by stirringfor 15 minutes. Methyl iodide (740 muL) was added thereto, followed by stirring for 1 hour. Ethyl acetate wasadded thereto, then, the organic layer was washed with a saturated aqueous sodium chloride solution, anddried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtainedresidues were purified by silica gel column chromatography (hexane:ethyl acetate=9:1?1:1), wherebymethyl 2-(methoxymethyl)isonicotinate (370 mg) was obtained as a colorless oily material

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58481-17-7, Methyl 2-(hydroxymethyl)isonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; FUJIFILM Corporation; KUBO, Yohei; ANDO, Makoto; TANAKA, Hidehiko; OSAKA, Shuhei; MATSUMOTO, Takuya; NAKATA, Hiyoku; TERADA, Daisuke; NITABARU, Tatsuya; (379 pag.)US2016/168139; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem