Pyridine-derivatives

Synthetic Route of 1822-51-1, 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. 1822-51-1, name is 4-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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.

[00324] A solution of acetyl chloride (6.34 mL, 0.084 mol, 4 equiv) dissolved in anhydrous EtOH (50 mL) was stirred for 0.5 h and added to a solution of homopiperazine (10.4 g, 0.1 mol, 5 equiv) in EtOH (250 mL). The reaction mixture was heated to reflux for 1 h, cooled to 25 C. and a solution of 4-picolyl chloride hydrochloride 93.44 g, 0.021 mol) in EtOH (40 mL) was added. The reaction mixture was heated to reflux for 16 h, cooled to 25 C. and the solvent was removed under vacuum. The residue was diluted with CH2Cl2 (300 mL) and was washed with 2N KOH (1×300 mL). The aqueous layer was extracted with CH2Cl2 (1×300 mL) and the organic phase was washed with 2N KOH (150 mL), dried (MgSO4) and concentrated. Chromatography (SiO2, 5% H2O-5% NH4OH-1PrOH) afforded the desired product (2.88 g, 4.01 g theoretical, 72%) as a yellow oil. TLC Rf 0.45 (5% H2O-5% NH4OH-1PrOH): 1H NMR (CDCl3, 300 MHz) delta 8.77 (d, J=5.9 Hz, 2H), 7.53 (d, J=5.7 Hz, 2H), 3.91 (s, 2H), 3,19 (m, 4H), 2.92 (m, 4H), 2.04 (m, 2H).

According to the analysis of related databases, 1822-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teijin Intellectual Property Center Limited; Combichem, Inc.; US6686353; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6975-44-6, Ethyl 4,6-dihydroxynicotinate, 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, SDS of cas: 6975-44-6, blongs to pyridine-derivatives compound. SDS of cas: 6975-44-6

A mixture of scheme 1 compound 2 (8.01 g, 43.7 mmol) and POCl3 (70 mL, 751.1 mmol) was stirred at 110 C for 2h. TLC showed the starting material was consumed completely. After cooling down, most of POCl3 was removed under vacuum. The residue was mixed with ice-water, and neutralized with sodium carbonate solution. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous Na2S04 , concentrated to give scheme 1 compound 3 (8.7 g) as a brown solid which was used in the next step immediately without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6975-44-6, Ethyl 4,6-dihydroxynicotinate, and friends who are interested can also refer to it.

Reference:
Patent; MANNKIND CORPORATION; TOLERO PHARMACEUTICALS, INC.; ZENG, Qingping; FARIS, Mary; MOLLARD, Alexis; WARNER, Steven L.; FLYNN, Gary A.; WO2014/52365; (2014); 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.54664-55-0, name is 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridine, molecular formula is C8H8ClN, molecular weight is 153.61, as common compound, the synthetic route is as follows.Product Details of 54664-55-0

Example A8; Preparation of intermediate 21A mixture of 4-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.0520 mol), Pd(OAc)2 (0.1 g), l,3-bis(diph-rhohosrhohino)rhororhoane (0.4 g) and KOAc (10 g) in TetaF (100 ml) and H2O (20 ml) was stirred under 50 atm. of CO for 16 hours at 150 0C. The mixture was evaporated and water was added. The precipitate was filtered off and dried, yielding 9.20 g (100%) of intermediate 21.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54664-55-0, 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/118903; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 869557-43-7, 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. 869557-43-7, name is 2-Amino-3-bromo-5-fluoropyridine. A new synthetic method of this compound is introduced below.

NaN02 (1.4 g, 14.4 mmol) was added in portions to a solution of 3-bromo-5- fluoro-pyridin-2-ylamine (5.2 g, 17.3 mmol) in a HF/pyridine mixture (40 mL) in a polyethylene reaction vessel. The resulting mixture was stirred at 0 C for 0.5 h, then heated to 50 C and stirred for 1 h. The reaction mixture was poured onto crushed ice, partially neutralized with Na2C03, and extracted with EtOAc. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated to give the product (4.1 g, 68%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,869557-43-7, 2-Amino-3-bromo-5-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65515-28-8, 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.65515-28-8, name is Methyl 2,6-dichloronicotinate, molecular formula is C7H5Cl2NO2, molecular weight is 206.03, as common compound, the synthetic route is as follows.

A 250 mL eggplant flask was sequentially charged with methyl 2,6-dichloronicotinate (2.06 g, 10 mmol), 4-(tertbutyl)phenol (1.50 g, 10mmol), and 12 mL of N, N-dimethylformamide for dissolving them. Triethylamine (1.80 mL, 13mmol) was added dropwise under stirring at room temperature, and after completion of the dropwise addition, triethylenediamine (168 mg, 1.50 mmol) was added. The mixture was stirred at room temperature for 4-5 hours and the solutionchanged from clear to turbid. Thin layer chromatography [V (petroleum ether) / V (ethyl acetate) = 6/1] detected thatmost of the raw material disappeared. Then, 1.30 mL of HOAc, 25 mL of isopropanol and 15 mL of ice water weresequentially added while the solution changed from turbid to clear, and stirred at room temperature for 0.5 hour. 40 mLof water was slowly dropwise added, and after completion of the dropwise addition, stirred at room temperature for 2hours. A large number of white solid precipitated and was filtered. The filter cake was washed with a mixed solution ofisopropyl alcohol / water = 1: 1 and dried under vacuum at 50 C for 8 hours to obtain 2.60 g of methyl 6-(4-(tertbutyl)phenoxy)-2-chloronicotinate as a solid, 81.50%

Statistics shows that 65515-28-8 is playing an increasingly important role. we look forward to future research findings about Methyl 2,6-dichloronicotinate.

Reference:
Patent; Shenyang Sunshine Pharmaceutical Co., Ltd.; ZHOU, Yunlong; CAI, Suixiong; WANG, Guangfeng; JIAO, Lingling; MIN, Ping; JING, Yu; GUO, Ming; (44 pag.)EP3275881; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75903-58-1, 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. 75903-58-1, name is 6-Aminopyridine-2-sulfonamide, molecular formula is C5H7N3O2S, 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.

[001308] 2-Chloro-6-(3-fluoro-5-isobutoxy-phenyl)pyridine-3-carboxylic acid (3.00 g, 9.27 mmol) was dissolved in N,N-dimethylformamide (30.00 mL), and 1,1?- carbonyldiimidazole (2.254 g, 13.90 mmol) was added to the solution. The solution was allowed to stir at 65 C for 1 hour. In a separate flask, sodium hydride (444.8 mg, 11.12 mmol) was added to a solution of 6-aminopyridine-2-sulfonamide (1.926 g, 11.12 mmol) in N,N-dimethylformamide (15.00 mL). This mixture was stirred for one hour before being added to the prior reaction mixture. The final reaction mixture was stirred at 65 C for 15 minutes. Volatiles were removed under reduced pressure. The remaining oil was taken up in ethyl acetate and washed with aqueous hydrochloric acid (1 N, 1 × 75 mL) and brine (3 × 75 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The remaining white solid (4.7 g) was fully dissolved in isopropanol (120 mL) in an 85 C water bath. The colorless solution was allowed to slowly cool to room temperature with slow stirring over 16 hours. The crystalline solids that had formed were collected by vacuum filtration, and then rinsed with cold isopropanol (50 mL). Upon drying, N-[(6-amino-2- pyridyl)sulfonyl]-2-chloro-6-(3-fluoro-5-isobutoxy-phenyl)pyridine-3-carboxamide (3.24 g, 6.76 mmol, 73%) was obtained as a white solid. 1H NMR (400 MHz, DMSO- d6) delta 12.78 (s, 1H), 8.15 (d, J = 8.0 Hz, 1H), 8.09 (d, J = 7.9 Hz, 1H), 7.73 – 7.63 (m, 1H), 7.49 (dd, J = 8.6, 1.9 Hz, 2H), 7.21 (d, J = 7.3 Hz, 1H), 6.99 (dt, J = 10.7, 2.2 Hz, 1H), 6.74 (d, J = 8.4 Hz, 1H), 6.64 (s, 2H), 3.86 (d, J = 6.5 Hz, 2H), 2.05 (dp, J = 13.3, 6.5 Hz, 1H), 1.02 (dd, J = 12.7, 6.4 Hz, 6H).

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 75903-58-1, 6-Aminopyridine-2-sulfonamide.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BEAR, Brian; CLEMENS, Jeremy; CLEVELAND, Thomas; COON, Timothy, Richard; GROOTENHUIS, Peter, Diederik Jan; FRIEMAN, Bryan, A.; HADIDA RUAH, Sara S.; KHATUYA, Haripada; KRENITSKY, Paul, J.; MILLER, Mark, Thomas; SILINA, Alina; UY, Johnny; ZHOU, Jinglan; (528 pag.)WO2017/173274; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13534-97-9, Adding some certain compound to certain chemical reactions, such as: 13534-97-9, name is 6-Bromopyridin-3-amine,molecular formula is C5H5BrN2, 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 13534-97-9.

Example 1; Preparation of intermediates N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide (1D) and N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(trifluoromethyl)benzamide (1E); Step A: Commercially available 6-bromopyridin-3-amine (1A, 20 g, 1.0 equivalent) was added in portions to a solution of potassium thiocyanate (5.0 equivalents) in acetic acid (0.4 M) at -5° C. After addition, the mixture was cooled to -15° C., and a solution of Br2 (1.3 equivalent) in acetic acic (9.4 M) was added drop wise via an additional funnel. The mixture was then warmed to room temperature and stirred for 12 h. The resulting precipitate was filtered; 100 mL EtOAc and 200 mL H2O were added to the filtrate and then 200 mL of solvent was removed in vacuo. The residue was stirred in ice bath for 10 minutes, and then the resulting precipitate was collected by filtration and washed twice with cold 10percent MeOH in Et2O. The filtrate was concentrated and the product was crystallized in ice bath to obtain a second crop of product after washing twice with cold 10percent MeOH in Et2O. The product 1B (77percent) was obtained as a brown solid after drying under vacuum, and then used without further purification. 1H NMR (400 MHz, DMSO-d6) delta ppm 4.94 (br. s., 1H) 7.44 (d, J=8.34 Hz, 1H) 7.57 (d, J=8.34 Hz, 1H) 8.04 (br. s., 1H); ESI-MS: m/z 230.0 (M+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. 13534-97-9, 6-Bromopyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/318425; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 74976-31-1, Adding some certain compound to certain chemical reactions, such as: 74976-31-1, name is 6-Chloro-1H-pyrrolo[3,2-c]pyridine,molecular formula is C7H5ClN2, 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 74976-31-1.

To a solution of6-chloro-1H-pyrrolo[3,2-c]pyridine (5.00 g, 32.8 mmol) in DMF(20 mL) was added NaH (1.57 g, 39.3 mmol) at 0C. The reaction mixture was stirred for1 h, then SEM-Cl (6.56 g, 39.3 mmol) was added at 0C. The reaction mixture wasstirred at room temperature for 1 h, then quenched with HzO (100 mL) and extracted withDCM (3 x 100 mL). The organic layer was separated and washed with brine (3 x 10025 mL), then dried over anhydrous NazS04 and concentrated in vacuo. The crude materialwas purified by column chromatography (10-15% EtOAc in hexanes) to afford the titlecompound (7.00 g, 75%) as a yellow oil. DH (400 MHz, CD30D) -0.07 (s, 9H), 0.87 (t, J7.83 Hz, 2H), 3.52 (t, J7.83 Hz, 2H), 5.57 (s, 2H), 6.71 (d, J2.93 Hz, 1H), 7.50 (d, J3.42Hz, 1H), 7.64 (s, 1H), 8.61 (s, 1H). HPLC-MS (method 6): MH+ m/z 283.3, RT 2.1230 minutes.

According to the analysis of related databases, 74976-31-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; DEBOVES, Herve Jean Claude; FOLEY, Anne Marie; FOULKES, Gregory; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; QUINCEY, Joanna Rachel; SCHULZE, Monika-Sarah Elisabeth Dorothea; SELBY, Matthew Duncan; SMALLEY, Adam Peter; TAYLOR, Richard David; TOWNSEND, Robert James; ZHU, Zhaoning; (278 pag.)WO2018/229079; (2018); 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. 59786-31-1, name is Methyl 3-bromoisonicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-bromoisonicotinate

Example 55 Synthesis of (S)-N-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)-3-(5-methylfuran-2-yl)isonicotinamide Compound 106a. To a stirred solution methyl 3-bromoisonicotinate (0.300 g, 1.4 mmol, 1.0 equiv) in Dioxan (5 mL) and water (5 mL), was added (5-methylfuran-2-yl)boronic acid (0.212 g, 1.68 mmol, 1.2 equiv), Na2CO3 (0.297 g, 2.8 mmol, 2.0 equiv) and aerated the reaction mixture with nitrogen for 15 min and added Dichlorobis(triphenylphosphine)palladium(II) (0.098 g, 0.14 mmol, 0.1 equiv). Aerated the reaction mixture again with nitrogen for 15 min. The mixture was allowed to stir at 100 C. for 2 h. Product formation was confirmed by LCMS. The reaction mixture was diluted with water (50 mL) and washed with ethyl acetate (20 mL*2). Aqueous layer was separated and freeze dried over lyophilizer to obtain 3-(5-methylfuran-2-yl)isonicotinic acid (0.250 g).

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, 59786-31-1, Methyl 3-bromoisonicotinate.

Reference:
Patent; Praxis Biotech LLC; ALFARO, Jennifer; BELMAR, Sebastian; BERNALES, Sebastian; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; US2019/185451; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 76006-08-1 , The common heterocyclic compound, 76006-08-1, name is 5-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a solution of 5-chloro-lH-pyrazolo[3,4-c]pyridine (130 mg, 0.847 mmol) dissolved in N,N-dimethylformamide (5.00 ml) was added cesium carbonate (579 mg, 1.778 mmol) followed by tert-butyl 4-((methylsulfonyl)oxy)-2-oxopiperidine-l-carboxylate (273 mg, 0.931 mmol). The reaction mixture stirred at room temperature overnight. LC/MS analysis indicated that the desired product was not obtained. The reaction was heated to 65C and stirred overnight. The mixture was filtered through a 0.2 mm Millex syringe-driven filter unit, washed with methanol (2 x 6 mL) and concentrated to dryness under reduced pressure. The crude mixture was purified by reverse phase HPLC (10% to 90% AcetonitrileAVater + 0.1% TFA, over 10 minutes) to provide the desired product tert-butyl 4-(5-chloro-lH-pyrazolo[3,4-c]pyridin-l- yl)-2-oxopiperidine-l -carboxylate. LCMS (ESI) calc’d for C16H19CIN4O3 [M+H]+ = 351, found 351

The synthetic route of 76006-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SILIPHAIVANH, Phieng; METHOT, Joey; LIPFORD, Kathryn Ann; MOLINARI, Danielle; SLOMAN, David, L.; WITTER, David; ZHOU, Hua; BOYCE, Christopher; HUANG, Xianhai; LIM, Jongwon; GUERIN, David; KARUNAKARAN, Ganesh Babu; BAKSHI, Raman Kumar; LIU, Ziping; FU, Jianmin; WAN, Zhilong; LIU, Wei; (216 pag.)WO2016/100050; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem