Tag: M.W:100-200

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. 10177-31-8, name is 4-Methoxynicotinic acid. A new synthetic method of this compound is introduced below., name: 4-Methoxynicotinic acid

[0350] A solution of 4-(4-(2,4-difluorophenoxy)piperidin-l -yl)-6-methoxypyridin-3-amine (40 mg, 0.1 19 mmol), 4-methoxynicoiinic acid (36.5 mg, 0.239 mmol), HATU (91 mg, 0.239 mmol) and DIPEA (0,052 mL, 0,298 mmol) m NMP (0.5 mL) was heated at 50C for 8 hours. More HATU (50 rng) was added and the reaction mixture was heated at 50C for 17 hours. The solution was diluted with DMF (0.3 mL) and MeOH (0.2 mL) and purified by preparative HPLC, eluting with ACN/water (basic mode) to give the title compound as a white solid (34 mg, 61 %). NuMKappa (500 MHzeta, DMSO-ifc) delta ppm 1.74 – 1.84 (m, 2 H), 2.04 (ddd, J=9.52, 6.35, 3, 17 Hz, 2 H), 2.90 (ddd,./ 12.08. 8.91, 2.93 Hz, 2 H), 3.19 – 3.27 (rn, 2 H), 3.83 (s, 3 H), 4.07 (s, 3 H), 4.51 (tt, J-8.05, 3.91Hz, 1H), 6.48 (s, 1H), 6.97 – 7.05 (m, 1H), 7.25 – 7.34 (m, 3 H), 8.56 (s, 1 1 1). 8.61 (d,.7=5.86 Hz, 1H), 8,90 (s, 1H), 9.65 (s, 1H); ESI-MS m/z [M+H]+ 471.

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, 10177-31-8, 4-Methoxynicotinic acid.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); 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.867267-24-1, name is 2,5-Dimethoxypyridine, molecular formula is C7H9NO2, molecular weight is 139.1519, as common compound, the synthetic route is as follows.Recommanded Product: 867267-24-1

General procedure: At -78 C., lithium diisopropylamide (2 M in tetrahydrothranlheptane/ethylbenzene) was added to a solution of the appropriate pyridine derivative in tetrahydrofuran (3 ml/mmol), the mixture was stirred for 2-4 h and triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2-3 hand then slowly thawed to RT overnight. Afier addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.;11.53 g (82.9 mmol) of 2,5-dimethoxypyridine were reacted according to General Method l. The desired product precipitated out after acidification of the aqueous phase. Yield: 9.53 g (61% of theory)10599] LC/MS [Method 1]: R=0.47 mm; MS (ESIpos):mlz=184 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,867267-24-1, 2,5-Dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHRIG, Susanne; HILLISCH, Alexander; STRASSBURGER, Julia; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; BUCHMUeLLER, Anja; GERDES, Christoph; SCHAeFER, Martina; TELLER, Henrik; JIMENEZ NUNEZ, Eloisa; SCHIROK, Hartmut; KLAR, Juergen; (66 pag.)US2016/272637; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74420-15-8, 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. 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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.

[0393] 3-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine: [0394] 3-bromo-lH-pyrrolo[2,3-b]pyridine (10.7 kg, 54.3 moles) was added to 94.3 kg of THF in a 200 L glass-lined reactor. The solid was dissolved completely by stirring. After the mixture was cooled to about 10-15 C, NaH (3.4 kg, 85 moles) was added in portions (about 200-250 g each portion) every 3 to 5 minutes while venting any gas released by the reaction. After the addition of NaH, the mixture was stirred for one hour while maintaining the temperature of about 10-20 C. 4-methylbenzenesulfonylchloride (12.4 kg, 65.0 moles) was added at a rate of 0.5 kg/10 minutes at about 10-20 C. After the addition was complete, the temperature was maintained at about 10-20 C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the peak area of 3-bromo-lH-pyrrolo[2,3-b]pyridine was less than 1% (after about 1.5 hours). Typical retention time for 3-bromo-l-tosyl-lH-pyrrolo[2,3- bjpyridine was 20.2 minutes. [0395] The reaction was quenched with water (10.7 kg) while maintaining the temperature below 20 C. Dichloromethane (41.3 kg) was added to the mixture. Then 3% HC1 acid (42.8 kg) was added into the mixture while maintaining the temperature below 25 C. After the addition, the phases were allowed to separate for 0.5 hour. The aqueous phase was extracted twice with dichloromethane. During each extraction, the mixture was stirred for 15 minutes and then held for 15 minutes. All the organic phases were combined. The combined organic phases were washed with 3% HC1 acid (33.4 kg) and water (40 kg). During each wash, the mixture was stirred for 15 minutes and then held for 30 minutes. [0396] The mixture was transferred into a 50 L vacuum filter and filtered through silica gel (3 kg). The cake was washed with dichloromethane (35 kg) twice. The filtrate and washings were combined. The organic phase was concentrated below 40 C under vacuum of a pressure less than -0.085 MPa until 10 L mixture remained. Petroleum ether (9 kg) was added into the residue. The mixture was stirred until it was homogeneous. The slurry was transferred into a 50 L vacuum filter and filtered. The cake was washed with petroleum ether (9 kg). A light brown solid resulted (17 kg, 99.7% purity as measured by HPLC analysis (method A), 94% yield of 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine).

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 74420-15-8, 3-Bromo-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HOOCK, Thomas Carl; CHAVAN, Ajit Bhiwaji; CHEN, Yingxue; GARG, Varun; HUANG, Jiayin; MAHNKE, Lisa Ann; ROBERTSON, Sarah Marie; SEWELL, Kathryn Lea; TAYLOR, Lori Kell; WO2014/201332; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6937-03-7, Adding some certain compound to certain chemical reactions, such as: 6937-03-7, name is Methyl 2-aminoisonicotinate,molecular formula is C7H8N2O2, 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 6937-03-7.

General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product.

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. 6937-03-7, Methyl 2-aminoisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Yanchun; Wang, Yuexiu; Xue, Han; Cao, Shuxia; Zhao, Yufen; Tetrahedron; vol. 75; 11; (2019); p. 1481 – 1491;,
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. 5832-44-0, name is 4-Methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-Methyl-3-nitropyridine

Example 6; Scheme F; A mixture of f-1 (0.0094 mol) and paraformaldehyde (0.0075 mol) in DMSO (4.5 ml) and triton B (0.35 ml) was stirred at 90C for 4 hours, and then purified by column chromatography over silica gel (eluent: CH2Cl2; 15mum). The pure fractions were collected and the solvent was evaporated, yielding: 0.15 g of intermediate f-2 (10%).

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, 5832-44-0, 4-Methyl-3-nitropyridine.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/136562; (2006); 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. 10592-27-5, name is 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below., COA of Formula: C7H8N2

To a solution of sulfurisocyanatidic chloride (23 mg, 0.17 mmol) in DCM (1 mL) in an ice-water bath was added a solution of Intermediate GW-17.2 (60 mg, 0.17 mmol) and DIPEA (0.06 mL, 0.33 mmol) in DCM (1 mL) and the reaction mixture was stirred for 2 min. Then a solution of 2,3-dihydro-lH-pyrrolo[2,3-b]pyridine (30 mg, 0.25 mmol) in DCM (1 mL) was added, followed by DIPEA (0.1 mL, 0.66 mmol) and the reaction mixture was stirred for 2 min. The bath was removed, the reaction mixture was stirred at rt for 2 h, concentrated, the residue was redissolved in DMF and purified by preparative HPLC to afford the title compound (9.9 mg). LC-MS retention time = 2.54 min; m/z = 517.20 [M+H]+. (Column: Phenomenex C18 2.0 X 50 mm, 3 muiotaeta particles; Mobile Phase A: 10% MeOH-90% H2O-0.1% TFA; Mobile Phase B: 90% MeOH-10% H2O-0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 4 min, then a 1-min hold at 100% B; Flow: 0.8 mL/min; Detection: UV at 220 nm).

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, 10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 24242-20-4, 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. 24242-20-4, name is 5-Aminopicolinic acid, molecular formula is C6H6N2O2, 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 solution of 5-aminopyridiencarboxylic acid (16; 8.4 g, 60.8 mmol) inethanol ( 100 mL) was added SOO2 (14.5g, 120 mmol) at 0 C. The mixture was refluxed for 1 2 h. The solvent was removed and saturated Na2C03 solution was added to adjust pH=9 and fi ltrated to give a solid. Dried in vacuo to give ethyl 5-aminopicolinate ( 17; 7.5 g? 75%). M S (ESI) calcd forC8H,oN202 (m/z) 166.18.

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 24242-20-4, 5-Aminopicolinic acid.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; NG, Pui, Yee; BLUM, Charles; MCPHERSON, Lauren; PERNI, Robert, B.; VU, Chi, B.; AHMED, Mohammed, Mahmood; DISCH, Jeremy, S.; WO2011/59839; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100367-39-3, Adding some certain compound to certain chemical reactions, such as: 100367-39-3, name is 4-Bromo-2-methoxypyridine,molecular formula is C6H6BrNO, 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 100367-39-3.

To a resealable reaction pressure vessel under nitrogen wasadded 1.0 equiv of 9 (266 mg, 0.665 mmol), Pd(PPh3)4 (38 mg,0.033 mmol, 5 mol %), K2CO3 (184 mg, 1.33 mmol, 2.0 equiv), 2-methoxy-4-bromopyridine (137 mg, 0.732 mmol, 1.1 equiv),dioxane (20 mL) and water (2 mL). The mixture was degassedthrough bubbling nitrogen for 40 min and heated at 110 C overnight.After cooling to room temperature, water (20 mL) wasadded and the organic product was extracted using EtOAc(3 30 mL). The combined organic layers were dried overMgSO4, filtered through Celite and the solvent removed in vacuo.The residual was purified on a silica gel column eluted withEtOAc/hexanes to provide 160 mg (63%) of 8e as a colorless oil.

According to the analysis of related databases, 100367-39-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ondachi, Pauline W.; Ye, Zhuo; Castro, Ana H.; Luetje, Charles W.; Damaj, M. Imad; Mascarella, S. Wayne; Navarro, Hernan A.; Carroll, F. Ivy; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5693 – 5701;,
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.14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.Computed Properties of C5H5ClN2

Intermediate 252A: 2-chloro-5-iodopyridin-4-amine To a stirred solution of 2-chloropyridin-4-amine (5 g, 39 mmol) in DMF (50 mL) was added NIS (8.75 g, 39 mmol). The reaction mixture was then heated at 80 C for 3 h. The mixture was cooled and the DMF removed in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The organic layer was dried over Na2S04, filtered, and concentrated. The product was purified via column chromatography (10% EtO Ac/pet ether) to afford 2-chloro-5-iodopyridin-4-amine (4 g, 39% yield). LCMS: 254.8 (M+). Further elution with 12% EtO Ac/pet ether afforded 2- chloro-3-iodopyridin-4-amine (4 g, 39% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14432-12-3, 4-Amino-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GARDNER, Daniel S.; SANTELLA, Joseph B.; PAIDI, Venkatram Reddy; WU, Hong; DUNCIA, John V.; NAIR, Satheesh Kesavan; HYNES, John; (300 pag.)WO2016/210034; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63071-03-4 ,Some common heterocyclic compound, 63071-03-4, molecular formula is C7H9NO, 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.

Step A: methyl 2-(6-methoxypyridin-2-yl)acetate To the solution of LDA (18.3 mL, 36.5 mmol) in THF (120 mL) cooled to -78 C. was added 2-methoxy-6-methylpyridine (1.5 g, 12.2 mmol) in THF (15 mL) dropwise, and then the mixture was stirred at -78 degree for 2 h. Dimethyl carbonate (1.2 mL, 14.6 mmol) was added quickly and continued to stir at -78 C. for 15 min. The reaction was quenched by H2O at -78 C. The solution was extracted with ethyl acetate, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified with a standard method to give desired compound. _?H NMR (CHEOROFORM-d) oe: 7.55 (dd, J8.3,7.3 Hz, 1H), 6.85 (d, J7.3 Hz, 1H), 6.65 (d, J8.3 Hz, 1H),3.92 (s, 3H), 3.77 (s, 2H), 3.74 (s, 3H). EC-MS: mlz (M+H)182.6.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63071-03-4, its application will become more common.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC; Lemieux, Rene M.; Popovici-Muller, Janeta; Salituro, Francesco G.; Saunders, Jeffrey O.; Travins, Jeremy; Chen, Yongsheng; US2014/142081; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem