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. 53636-70-7, name is 6-Methyl-2,3-pyridinedicarboxylic acid, molecular formula is C8H7NO4, 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: 53636-70-7

In a 100 ml round-bottomed flask 6-methyl-2,3-pyridinedicarboxylic acid (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 C. under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D40 (8.2 g) as a slightly brown solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.41 (d, 1H), 7.82 (d, 1H), 2.73 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 53636-70-7.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 133081-25-1, name is 6-(2-(tert-Butoxycarbonyl)hydrazinyl)nicotinic acid. A new synthetic method of this compound is introduced below., Formula: C11H15N3O4

A mixture of 2-chloro-4,6-dimethyl-1,3,5-triazine (CDMT) (1.76 g, 10 mmol), 2 (2.53 g, 10 mmol) in THF (10 ml), and N-methylmorpholine (1.1 ml, 10 mmol) and after 4 h 4d (3.40 g, 10 mmol) in THF were combined as above to afford 5d as yellow solid. Compound 5d: mp 176-178 C; yield 36%; IR (KBr) nu (cm-1): 1522.7, 1636.0, 1719.2, 2853.6, 2926.7, 3251.6; 1H NMR (CD3OD) (delta ppm): 8.5 (1H, m, ArH), 8.3 (1H, d, J = 8.7 Hz, ArH), 8.0 (1H, m, ArH), 7.7 (1H, m, ArH), 7.6 (1H, m, ArH), 7.5 (1H, t, J = 5.3 Hz, ArH), 6.7 (1H, d, J = 8.9 Hz, CCHC), 4.6 (2H, s, NH), 3.9-4.0 (2H, m, NHCH2), 3.3 (3H, m, NH,CH2), 3.0 (2H, m, CH2), 2.7 (2H, m, CH2), 2.3 (1H, m, NH), 1.9 (4H, m, CH2), 1.8 (2H, m, CH2), 1.6 (4H, m, CH2), 1.3-1.4 (9H, s, BOC), 1.3 (8H, br, CH2); MS (FAB) m/z (M + 1) 575.4, 475.4, 197.1; MS-HR (FAB) Calcd for C33H46N6O3: 574.36314. Found: 575.36921 (M + 1).

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, 133081-25-1, 6-(2-(tert-Butoxycarbonyl)hydrazinyl)nicotinic acid.

Reference:
Article; Szymanski, Pawel; Markowicz, Magdalena; Mikiciuk-Olasik, Elbieta; Bioorganic Chemistry; vol. 39; 4; (2011); p. 138 – 142;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 915107-31-2, 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. 915107-31-2, name is Methyl 6-chloro-5-methoxynicotinate, molecular formula is C8H8ClNO3, 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.

To a stirred solution of 6-chloro-5-methoxy-nicotinic acid methyl ester (0.5g, 2.48mmol) in anhydrous THF (20mL) cooled to 0 C under nitrogen, LiAIH4 (104mg, 2.728mmol) was added. The reaction was allowed to warm to rt for 2 hrs. The reaction was cooled to 0 C and quenched with water (5mL). Potassium sodium tartrate ( ochelle’s salt) was added to help break up the suspension. The mixture was filtered through Celite, washing well with water (20mL) and ethyl acetate (lOOmL). The filtrate was collected and the layers separated. The aqueous extracted with ethyl acetate (3 x 20mL). The combined organic layers were washed with brine (50mL), dried over MgS04 and the solvent removed in vacuo. The crude was purified by flash chromatography (silica) eluting in step gradients up to 40% Pet. Ether, 60% ethyl acetate. Pure fractions were concentrated affording the title compound (6- chloro-5-methoxy-pyridin-3-yl)-methanol as a white solid (360mg, 2.074mmol, 84% yield). [M+H]+ = 174

According to the analysis of related databases, 915107-31-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KALVISTA PHARMACEUTICALS LIMITED; DAVIE, Rebecca Louise; EDWARDS, Hannah Joy; EVANS, David Michael; HODGSON, Simon Teanby; MILLER, Iain; NOVAK, Andrew Richard; SMITH, Alun John; STOCKS, Michael John; WO2014/188211; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 144657-66-9, 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. 144657-66-9, name is tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, molecular formula is C13H14N2O3, 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.

A mixture of l-(fer?-butyloxycarbonyl)-3-formyl-7-azaindole (Int-16, 9.8 g, 40 mmol) and sodium borohydride (1.7 g, 44 mmol) in methanol (50 mL) were stirred at rt for 4 h. TLC showed the reaction was complete. Water was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with water, brine, dried, concentrated, and purified by flash column chromatography to afford alcohol Int-17 (8.4 g, 85%).

According to the analysis of related databases, 144657-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCEPION PHARMACEUTICALS, INC.; JIANG, Shan; XING, Xinglong; WANG, Qishan; KONG, Ren; WO2011/23081; (2011); 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 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

To compound 12 (50 mg, 0.27 mmol) and 2-aminophenol (35 mg, 0.32 mmol) was added a 1N aqueous sodium hydroxide solution (0.75 mL), and the mixture was heated in a microwave oven to 150 C for 10 min. It was then diluted with water and extracted twice with ethyl acetate. 4N HCl solution was added (pH 4), and the mixture was extracted again with ethyl acetate. The combined organic layers were dried over sodium sulfate, and the solvent was evaporated. The residue was purified by preparative HPLC to yield 52 mg (82%) of the title compound as a tan solid. 1H NMR (400 MHz, DMSO-d6): delta 7.44-7.52 (m, 3H), 7.89 (t, J=8.4Hz, 2H), 8.71 (d, J=4.4Hz, 1H), 8.76 (d, J=8.1Hz, 1H), 14.42 (br s, 1H). 13C NMR (125 MHz, DMSO-d6): delta 111.0, 113.3, 118.9, 119.8, 125.0, 125.8, 130.4, 131.9, 141.1, 149.5, 150.1, 152.3, 157.4. HRMS m/z calcd for C13H8N4O: 236.0698; found: 236.0698.

With the rapid development of chemical substances, we look forward to future research findings about 956010-87-0.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 23100-12-1, 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 23100-12-1, name is 6-Chloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Preparation of tert-butyl 4-((6-chloropyridin-3-yl)methyl)piperazine-1-carboxylate To a solution of 6-chloronicotinaldehyde (0.5 g, 2.68 mmol) and tert-butyl piperazine-1-carboxylate (0.6 g. 3.22 mmol) in DCE was added acetic acid (0.1 mL) and the reaction was stirred for 2 h at RT. Then NaBH(OAc)3 (1.7 g, 8.1 mmol) was added to the reaction portion-wise at RT. The reaction was stirred at RT for 16 hours. The reaction mixture was then concentrated. The crude material was dissolved in water and basified to pH 8-9 using saturated aqueous NaHCO3 solution. The mixture was extracted with EtOAc (2*25 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by preparative HPLC to afford tert-butyl 4-((6-chloropyridin-3-yl)methyl)piperazine-1-carboxylate (300 mg, 31% yield).

According to the analysis of related databases, 23100-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; DALES, Natalie; GORMISKY, Paul; KERRIGAN, John Ryan; SHU, Lei; (159 pag.)US2019/77773; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1040682-68-5, Adding some certain compound to certain chemical reactions, such as: 1040682-68-5, name is 1H-Pyrrolo[3,2-c]pyridine-4-carbonitrile,molecular formula is C8H5N3, 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 1040682-68-5.

To a solution of lH-pyrrolo[3,2-c]pyridine-4-carbonitrile (60.0 mg, 0.42 mmol , 1.0 eq), NIS (52.0 mg, 0.46 mmol, 1.1 eq) in DCM (4.0 mL) was stirred at rt for 2 h. After the reaction was complete, water was added, and the mixture was extracted with EA. The organic layer was washed with water, dried over Na2S04, filtered and concentrated. The resulting residue was purified by column chromatography (EA/PE = 1/1, v/v) to provide 3-iodo-lH-pyrrolo[3,2-c]pyridine-4-carbonitrile (160 mg, 97%).

According to the analysis of related databases, 1040682-68-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); 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 22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5ClN2O2

A mixture of 6-chioro-2-methyi-3-nitropyridine(8.6() g, 50.00 mrnol), NH4Ci (27.00 g, 500.0() mrnol) and Fe (14.0() g, 250.00 mrnoi) in MeOK(100 mL) was stirred at 80 C for 5 11 The mixture was filtered and concentrated, and theresulting residue was purified by column chromatography (Si02. eluting with PE:EA 5:1) toafford the title compound.

With the rapid development of chemical substances, we look forward to future research findings about 22280-60-0.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADAMS, Gregory, L.; COX, Jason, M.; DEBENHAM, John, S.; EDMONDSON, Scott; GILBERT, Eric, J.; GUO, Yan; JIANG, Yu; JOSIEN, Hubert; KIM, Hyunjin, M.; LAN, Ping; MIAO, Shouwu; PLUMMER, Christopher, W.; RAJAGOPALAN, Murali; SHAH, Unmesh; SUN, Zhongxiang; TRUONG, Quang, T.; UJJAINWALLA, Feroze; VELAZQUEZ, Francisco; VENKATRAMAN, Srikanth; SUZUKI, Takao; WANG, Nengxue; (182 pag.)WO2017/205193; (2017); A1;,
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.184416-83-9, name is 2,3-Dichloropyridin-4-amine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4Cl2N2

A mixture of tert-butyl ((l S)-l’-(3-iodo-l-(tetrahydro-2H-pyran-2-yl)-lH- pyrazolo[3,4-b]pyrazin-6-yl)-l,3-dihydrospiro[indene-2,4′-piperidin]-l-yl)carbamate (350.0 mg, 555.0 pmol, from Intermediate J), 2,3-dichloropyridin-4-amine (135.0 mg, 832.0 pmol, CAS 184416-83-9), XantPhos-Pd-G4 (47.6 mg, 55.4 pmol) and Cs2C03 (270.0 mg, 832.0 pmol) in PhMe (10 mL) was stirred at 100 C for 12 hours. The reaction mixture was concentrated and purified by silica gel column (EtOAc in petroleum ether = 0-30%) to give tert-butyl N-[(3S)-l’-{3-[(2,3-dichloropyridin-4-yl)amino]-l-(oxan-2-yl)-lH-pyrazolo[3,4- b]pyrazin-6-yl}-l,3-dihydrospiro[indene-2,4′-piperidin]-3-yl]carbamate (200.0 mg, 54% yield) as a yellow solid. LCMS m/z [M+H]+ = 665.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,184416-83-9, 2,3-Dichloropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14916-65-5, 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. 14916-65-5, name is 6-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 6-nitro-pyridin-3-ylamine (50 mg, 0.33 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 25 mg, 0.66 mmol), and the mixture was stirred at r.t for 30 min. Then 5-bromo-2-methoxy-benzenesulfonyl chloride (86 mg, 0.3 mmol) was added and the mixture was stirred at 50 C overnight. TLC showed that the reaction was complete. The resultant was concentrated in vacuum to remove DMF. The residue was diluted with DCM (30 mL) and the mixture was washed with IN HC1 (30 mL x3) .The organic layer dried over Na2S04 and concentrated to dryness in vacuum. The residue was purified by silica gel column (PE/EtOAc, 1/1) to give 30 mg (yield: 26%) of 5-bromo-2-methoxy-N-(6-nitro-pyridin-3-yl)- benzenesulfonamide as a brown solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14916-65-5, 6-Nitropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; DAHL, Russell; COSFORD, Nicholas, D.P.; MILLAN, Jose, Luis; WO2013/126608; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem