Category: pyridine-derivatives

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1018505-59-3

A solution of 5-(4-ethylpiperazin-1-yl)pyridin-2-amine (185 mg, 0.90 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (200 mg, 0.90 mmol) cesium carbonate (1.02 g, 3.13 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethlxanthene (77.7 mg, 0.13 mmol) in dioxane (10 ml) was flushed with argon before tris(dibenzylideneacetone)dipalladium(0) (61.5 mg, 0.07 mmol) was added and the resulting solution was heated at 90 C. for 18 h. The mixture was cooled to room temperature and diluted with dichloromethane and water. The layers were separated and the aqueous layer was extracted with dichloromethane (2*25 mL). The organic layers were combined, dried over magnesium sulfate. The resulting mixture was filtered and concentrated in vacuo. The residue was triturated with methanol and dichloromethane and filtered, washed with ether and dried to give 6-chloro-4-[5-(4-ethyl-piperazin-1-yl)-pyridin-2-ylamino]-2-methyl-2H-pyridazin-3-one (138 mg, 44%) as a yellow solid.

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, 1018505-59-3, 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine.

Reference:
Patent; Berthel, Steven Joseph; Billedeau, Roland Joseph; Brotherton-Pleiss, Christine E.; Firooznia, Fariborz; Gabriel, Stephen Deems; Han, Xiaochun; Hilgenkamp, Ramona; Jaime-Figueroa, Saul; Kocer, Buelent; Lopez-Tapia, Francisco Javier; Lou, Yan; Orzechowski, Lucja; Owens, Timothy D.; Tan, Jenny; Wovkulich, Peter Michael; US2012/40949; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1142363-52-7, 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. 1142363-52-7, name is JNJ-40346527. A new synthetic method of this compound is introduced below.

The salts and solid residues of Compound A were prepared using nine different acidic counter-ions, (wherein the acidic counter-ion is provided by the corresponding acid i.e., sulfuric, phosphoric, methanesulfonic, p-toluenesulfonic, benzenesulfonic, malonic, citric, 1 -malic, and acetic acids), using the following synthetic procedure; Nine samples of Compound A (about 20 mg) prepared as described in Example 1 were added to nine separate 4 mE vials. About 1.1 molar equivalents of the acid (i.e., sulfuric acid, phosphoric acid, methanesulfonic acid, p-toluenesulfonic acid, benzenesulfonic acid, malonic acid, citric acid, 1-malic acid, and acetic acid) solutions (0.1 M in acetone, freshly prepared) was independently added to each vial. The vials were stirred at 500 rpm and heat was applied as necessary. All solutions formed suspensions upon addition of the acid solution to Compound A, with the exception that the acetic acid solution remained a clear mixture. The suspensions were then heated to 40 C. with stirring for about 30 minutes, but no additional clear solutions were observed. Since the solubility of Compound A in acetone is about 130 mg/mE, the formation of a suspension was interpreted as an indication that a salt or other non-free base material (e.g. solvate, co-crystal, etc.) had formed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1142363-52-7, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; FAWZY, Nagy E.; Breslin, David; (52 pag.)US2018/16264; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 18699-87-1, 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.18699-87-1, name is 2-Methyl-3-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

To a solution of potassium ethoxide (2.44g, 27.7mmol) in diethyl ether (90ML) and ethanol (8mL) was added diethyl oxalate (3.79mL, 27. 7MMOL) resulting in a yellow suspension. The reaction mixture was stirred for 5min prior to the addition of 2-methyl-3-nitropyridine (Preparation 29,3. 40g, 24. 6MMOL) in one portion. The resulting red suspension was stirred at rt, under argon, for 20h. The mixture was filtered, washed thoroughly with diethyl ether and dried. The red solid was dissolved in water and the mixture adjusted to pH 4 by addition of glacial acetic acid. The resulting precipitate was collected by filtration, dissolved in dichloromethane, washed with brine, dried (MgS04), and then filtered and concentrated in vacuo to give the title compound as an orange solid. SN (CDCl3): 1.40 (3H, t), 4.39 (2H, q), 7.34 (1H, s), 7.36 (1H, dd), 8.43 (1H, dd), 8. 66 (1H, dd).

The chemical industry reduces the impact on the environment during synthesis 18699-87-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2004/104001; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 89488-30-2, name is 5-Bromo-3-methylpyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-Bromo-3-methylpyridin-2(1H)-one

To a suspension of starting material A (1.00 g; 5.053 mmol) and potassium carbonate (1.397 g; 10.105 mmol) in DMF (5 ml_) is carefully added iodomethane (0.346 ml5.558 mmol). The reaction mixture is stirred overnight (16 h) at room temperature. The reaction mixture is then quenched with 10 % ammonia solution (10 ml_) and 30 ml_ water is added. It is extracted with 3 x 50 mL EtOAc. The combined organic layer is dried with Na2S04, filtered and concentrated under reduced pressure to afford the product. Yield: 98 % (1.0 g; 4.95 mmol) ( HPLC-MS: (M+H)+ = 202/204; tRet = 0.65 min; method LCMS BAS1

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, 89488-30-2, 5-Bromo-3-methylpyridin-2(1H)-one.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; TONTSCH-GRUNT, Ulrike; BAUM, Anke; RUDOLPH, Dorothea Ingrid; (85 pag.)WO2019/145410; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 639091-75-1, 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.639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate, molecular formula is C12H16N2O4, molecular weight is 252.27, as common compound, the synthetic route is as follows.

To a solution of C-2 (239.0 g, 0.95 mol) in THF (2400 mL) was added a solution of lithium hydroxide (45.6 g, 1.9 mol) in water (600 mL). The mixture was stirred at rt overnight, and then diluted with water (1500 mL). Most of the THF was removed under reduced pressure. The pH of the mixture was adjusted to 3 with citric acid (saturated). The precipitated product was collected and dried to give C-3 (253.0 g, crude). MS (ESI) calculated for (C11H14N2O4) [M-H] , 237.1; found, 237.0.

The chemical industry reduces the impact on the environment during synthesis 639091-75-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1026201-52-4, 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. 1026201-52-4, name is 5-Bromoimidazo[1,2-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below.

Step1:tert-Butyl5-bromoimidazo[1,2-a]pyridin-2-ylcarbamate.Toastirredsolutionof5-bromoimidazo[1,2-a]pyridine-2-carboxylicacid(1.00g,4.15mmol,1.0eq.)int-BuOH(20mL)andtoluene(20mL)wasaddedDPPA(1.37g,5.00mmol,1.2eq.)atanice-waterbathtemperature.Et3N(0.70mL,5.00mmol,1.2eq.)wasthenaddeddropwise.Theresultantmixturewasheatedtorefluxfor14hrs.TLCindicatedthedisappearanceof5-bromoimidazo[1,2-a]pyridine-2-carboxylicacid.Thecrudereactionmixturewasconcentratedtodryness.Theresiduewaspurifiedbyacolumnchromatography(200-300meshsilicagel,PE/EA5/1)toaffordtert-butyl5-bromoimidazo[1,2-a]pyridin-2-ylcarbamate.1HNMR(400MHz,DMSO-d6)delta(ppm)10.14(br,1H),7.82(s,1H),7.47(d,J8.7Hz,1H),7.24(d,J6.8Hz,1H),7.16-7.20(m,1H),1.49(s,9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1026201-52-4, 5-Bromoimidazo[1,2-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; JN THERAPEUTICS; LI, Jin; WU, Shung; YANG, Minmin; CHEN, Sean; HAO, Wenshan; (148 pag.)WO2016/119700; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 188057-20-7, 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. 188057-20-7, name is 4-Iodopyridin-3-ol. A new synthetic method of this compound is introduced below.

Step 35-4.; To a solution of 3-hydroxy-4-iodopyridine (5.09 g, 23.0 mmol) in DMF (95 mL) were added (R)-propylene carbonate (T95-A, 2.35 g, 23.0 mmol)) and potassium carbonate (3.18 g, 23.0 mmol). The solution was stirred at 85 C. for 72 h. Water was added and the aqueous phase extracted with EtOAc (3×). The combined organic phases were washed with brine (1×) and water (1×), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (100% EtOAc) to give 1.4 g (24%) of T95-4(R).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,188057-20-7, 4-Iodopyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; Marsault, Eric; Fraser, Graeme L.; Benakli, Kamel; St-Louis, Carl; Rouillard, Alain; Thomas, Helmut; US2010/93720; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53710-18-2, 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. 53710-18-2, name is 3,5-Diiodopyridine. A new synthetic method of this compound is introduced below.

In a 75-mL sealed tube, 3,5-diiodo-pyridine (intermediate A-5, 6.6 g, 20 mmol), 5-chloro- 3,3-dimethyl-2,3-dihydro-isoindol-1-one (intermediate A-3, 1.95 g, 10 mmol), CuT (571 mg, 3 mmol), K3P04 (4.24 g, 20 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.7 mL, 6 mmol) were dissolved in 20 mL of dioxane. The resulting reaction mixture was heated at120C for 3 hours before it was poured into water (50 mL) and extracted with EtOAc (2 x125 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4,filtered and concentrated in vacuo to give a crude product, which was purified by silica gelflash chromatography (0-30% EtOAc-hexane gradient) to yield the title compound (1.8 g,45%) as a light yellow solid. MS: 399.2 (M+Hj.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53710-18-2, 3,5-Diiodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191340; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1190319-62-0, 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. 1190319-62-0, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, molecular formula is C7H5BrN2O, 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.

Pottasium tert-butoxide (0.03 g, 0.27 mmol) was added to a suspension of 6-bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (preparation 30c, 0.87 g, 4.1 mmol) in dimethylsulphoxide (4 mL) and, after stirring for 10 minutes at room temperature, the mixture was heated to 40-45 C and methyl acrylate (1.14 mL, 12.71 mmol) was added dropwise over 60 minutes. After the addition, the mixture was stirred for 2 hours and then further potassium tert-butoxide (1.4 g, 12.21 mmol) was added portionwise over 30 minutes keeping the temperature below 50 C. The mixture was then heated to 100 C and stirred for 2 hours. Water (20 mL) was added and heating was continued at 85 C for 2 hours and then the mixture was left to cool overnight. Ethyl acetate was added and the mixture was washed with water, brine, dried (MgSO4) and evaporated to give the title compound (0.60 g, 50%) as a white solid. LRMS (m/z): 293/295 (M-1)+. 1H-NMR delta (CDCl3): 2.14 (m, 2H), 2.27 (m, 2H), 2.73 (m, 2H), 3.01 (m, 2H), 7.40 (d, J=1.5 Hz, 1H), 8.29 (d, J=1.5 Hz, 1H), 8.44 (brs, 1H).

According to the analysis of related databases, 1190319-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2108641; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 136117-71-0, 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. 136117-71-0, name is (6-Bromoimidazo[1,2-a]pyridin-2-yl)methanol, molecular formula is C8H7BrN2O, 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.

Intermediate 38 (66.1 mg, 0.44 mmol) and (6-bromoimidazo[1 ,2-a]pyridin-2-yl)- methanol (100 mg, 0.44 mmol) were dissolved in acetonitrile (10 mL) and pyridiniumptoluenesulfonate (443 mg, 1.76 mmol) was added. The resulting mixture was heated at 80C overnight. The resulting mixture was cooled and evaporated onto silica. Purification by column chromatography (0-15% MeOH in DCM) gave a clear oil, whichwas freeze-dried to give the title compound (50 mg, 32%), 7:3 mixture of diastereomers, as a white solid.Major diastereomer (trans): H (400 MHz, DMSO-d6) 7.80 (dd, 1H, J0.6, 1.9 Hz), 7.57 (dd, 1H,J0.6, 8.8 Hz), 7.48 (m, 1H), 7.42 (m, 1H), 7.36 (dd, 1H,J9.5, 1.9 Hz), 7.29 (t, 1H,J7.3 Hz), 7.04 (d, 1H,J7.4 Hz), 6.97 (d, 1H,J2.5 Hz), 5.63 (qd, 1H,J6.3, 2.6 Hz), 5.22 (t, 1H, J5.7 Hz), 4.54 (m, 2H), 1.52 (d, 3H, J6.3 Hz.Minor diastereomer (cis): H (400 MHz, DMSO-d6) 7.78 (m, 1H), 7.57 (m, 1H), 7.48 (m, 1H), 7.42 (m, 1H), 7.36 (dd, 1H, J9.5, 1.9 Hz), 7.30 (t, 1H, J7.3 Hz), 6.92 (m,1H), 6.82 (d, 1H, J2.8 Hz), 5.40 (m, 1H), 5.28 (t, 1H, J5.7 Hz), 4.66 (d, 2H, J5.6 Hz),1.66 (d, 3H, J6.4 Hz). LCMS MH m/z 359.60.

According to the analysis of related databases, 136117-71-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; BROWN, Julien Alistair; CALMIANO, Mark Daniel; JONES, Elizabeth Pearl; KROEPLIEN, Boris; REUBERSON, James Thomas; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2015/86512; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem