Tag: M.W:100-200

Application of 1166828-13-2 ,Some common heterocyclic compound, 1166828-13-2, molecular formula is C7H6ClNO2, 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.

6-chloro-5-methyl-pyridine-2-carboxylic acid (0.85 g, 4.97 mmol) and sodium sulfite (CAN 7757-83-7, 1.5 g, 11.9 mmol) were added to water (3 mL) and ethanol (3 mL). The mixture was heated to 180C for 4 h in a sealed tube. After that the mixture was cooled to room temperature and a solid precipitated that was removed by filtration. The filtrate was concentrated and added to water (20 mL). The aqueous phase was washed with ethyl acetate (2 x 20 mL). Subsequently the aqueous phase was adjusted to pH = 2 with 2 N hydrochloric acid. Water was removed in vacuo to give the product as solid (1.2 g); MS (EI): m/e = 218.0 [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. 1166828-13-2, 6-Chloro-5-methylpyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); 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. 1053655-66-5, name is 7-Bromo-[1,2,4]triazolo[1,5-a]pyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 7-Bromo-[1,2,4]triazolo[1,5-a]pyridine

To the solution of compound 6-bromo-[l,2,4]triazolo[l,5-a]pyridine (0.2 g, 1 mmol), trimethyl borate (0.12g , 1.2 mmol) in toluene and THF (50 mL,V/V=4:l) was added /-BuLi (1.2 mL, 1.2 mmol, 1.0 M in hexane) at -780C. The reaction mixture was stirred for 1 h at -780C, then the reaction mixture was warmed to -150C and quenched with 2 N HCl (1 mL, 2 mol). The mixture was concentrated. Purification by chromatography (MeOH: DCM = 1 : 10) afforded [l,2,4]triazolo[l,5-a]pyridin-6-ylboronic acid (O. lOg, 55%) as light yellow solid. MS (m/z) (Mf+H): 164.

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, 1053655-66-5, 7-Bromo-[1,2,4]triazolo[1,5-a]pyridine.

Reference:
Patent; PROGENICS PHARMACEUTICALS, INC.; WO2009/155527; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13603-44-6, Adding some certain compound to certain chemical reactions, such as: 13603-44-6, name is 2,6-Dimethylpyridin-4-ol,molecular formula is C7H9NO, 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 13603-44-6.

Example 121: 2-(4-chloro-3-fluorophenoxy)-A^-(3-{2-[(2,6-dimethylpyridin-4- yl)oxy]acetamido}bicyclo[l.l.l]pentan-l-yl)acetamide (Compound 220) A mixture of Example 28A (65.0 mg, 0.180 mmol), 2,6-dimethylpyridin-4-ol (33.2 mg, 0.270 mmol), potassium carbonate (49.7 mg, 0.360 mmol), and potassium iodide (2.091 mg, 0.013 mmol) in acetone (2.5 mL) was heated at 140 C in a Biotage Initiator microwave reactor for 40 minutes. The reaction mixture was concentrated. The residue was treated with brine and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by HPLC (see protocol in Example 112D) to provide the title compound as a trifluoroacetic acid salt (53.2 mg, 53%). XH NMR (400 MHz, DMSO-c) delta ppm 8.88 (s, 1H), 8.72 (s, 1H), 7.47 (t, J = 8.9 Hz, 1H), 7.26 (s, 2H), 7.05 (dd, J = 11.4, 2.9 Hz, 1H), 6.83 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.79 (s, 2H), 4.46 (s, 2H), 2.57 (s, 6H), 2.25 (s, 6H). MS (ESI+) m/z 448.1 (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. 13603-44-6, 2,6-Dimethylpyridin-4-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farath; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (445 pag.)WO2017/193034; (2017); 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. 105250-17-7, name is (2-Aminopyridin-4-yl)methanol, molecular formula is C6H8N2O, 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. Safety of (2-Aminopyridin-4-yl)methanol

To a stirred solution of 67 (1.39 g, 11.2 mmol) in EtOH (46.5 ml)-water (6.5 ml) was added NaHCO3 (1.88 g, 22.3 mmol), followed by a 50percent w/w aqueous solution of chloroacetaldehyde (2.84 ml, 1.75 g, 22.4 mmol). The resultant suspension was stirred and refluxed for 2 h. The dark amber-colored reaction mixture was carefully concentrated (frothing) under reduced pressure to approximately half its original volume and then filtered. Collected solid was washed with MeOH. Combined filtrate and washings were concentrated in vacuo and yielded a dark, oily two-phase mixture. Treatment with EtOH produced a mixture of solid precipitate and a homogeneous liquid phase, which was filtered. The filtrate was concentrated under reduced pressure to a dark oil, which was purified via flash chromatography on silica gel, eluting with CH2CI2-CH3OH -NH4OH (91.5:8.5:0.25), to obtain compound 68 as a pale yellow solid (1.34 g; 80percent). To a solution of 68 (1.20 g, 8.10 mmol) in MeOH (5 ml) was added acetone (48 ml). A small amount of dark precipitate formed and was removed by filtration (0.45 muM syringe filter). To the clear yellow filtrate was added via syringe 1 M ethereal HCI (8.1 ml, 8.1 mmol). The resultant mixture was stirred briefly and was then filtered. The hygroscopic solid thus isolated was washed rapidly with acetone and dried under vacuum at 50 0C to obtain the hydrochloride salt of 68 as a tan powder (1.34 g; 89percent). EPO

With the rapid development of chemical substances, we look forward to future research findings about 105250-17-7.

Reference:
Patent; SCHERING CORPORATION; WO2007/1975; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15506-18-0, 1-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

[0625] To a solution of 2-(4-(2,4-difluorophenoxy)piperidin-l-yl)-5- (etaiotaomicronphi1etaomicron8Homicronetanu1)rhonupieta-3-3etapietaepsilon (50.00 mg, 1 10.0 muiotaetaomicron, 1.00 eq) and 1 -methyl -2 -oxo- 1,2- dihydropyridine-3-carboxylic acid (20.22 mg, 132.0 mutauetaomicron, 1.20 eq) in DMF (2 mL) was added HATU (62.75 mg, 165,02 muiotaetaomicron, 1.50 eq) and DIPEA (42.65 mg, 330.0 muetaiotaomicron, 57.64 mu,, 3.00 eq). The resulting mixture was stirred at 25C for 12 hours, then diluted with EtOAc (50 mL) and washed with saturated aq N’a >(*<) > (20 rnL) and brine (20 mL). The organic layers were dried over anhydrous NazSC filtered, concentrated in vacuo, and purified by preparative HPLC (basic mode) to give the title compound as a white solid (18 mg, 27%). .H NMR (400 MHz, CDCb) delta ppm 2.09 – 2.27 (m, 4 H), 3.01 – 3.15 (m, 4 H), 3.15 – 3.24 (m, 2 H), 3.54 – 3.63 (m, 2 H), 3.72 (s, 3 H), 3.75 – 3.85 (m, 4 H), 4.42 (dt,./ 7. 1. 3.5 Hz, 1H), 6.49 (t,./ 7. 1Hz, 1H), 6.74 – 6,83 (m, 1 I D. 6.87 (ddd, J=l 1.0, 8.4, 3.1Hz, 1H), 7.03 (td,,7=9.2, 5.5 Hz, 1H), 7.64 (dd, J=6.6, 1.8 Hz, 1H), 8.43 (d, J=2.2 Hz, 1H), 8.60 (dd, J=7.3, 2.0 Hz, 1H), 9.07 (d, J=2.2 Hz, 1H), 12.23 (s, 1H); ESI-MS m/z] M · Pi | 590.0.

The synthetic route of 15506-18-0 has been constantly updated, and we look forward to future research findings.

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

Adding a certain compound to certain chemical reactions, such as: 1065267-14-2, (3,5-Difluoropyridin-2-yl)methanol, 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, 1065267-14-2, blongs to pyridine-derivatives compound. category: pyridine-derivatives

(3,5-Difluoropyridin-2-yl)methyl 4-methylbenzenesulfonate (I-5)To a solution of (3,5-difluoropyridin-2-yl)methanol (0.25 g, 0.7 mmol) in tetrahydrofuran (THF; 10 mL) was added potassium hydroxide (KOH; 0.14 g, 2.55 mmol) at RT, and the mixture was stirred for 15 min p-Toluenesulfonyl chloride (0.42 g, 2.21 mmol) was added slowly at RT, and the reaction mixture was stirred for another 18 h. After complete consumption of the starting material (by TLC), the reaction mixture was diluted with H2O (50 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were washed with H2O (25 mL) and brine (25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 15% EtOAc/hexane afforded compound I-5 (0.18 g, 0.25 mmol, 35%) as colorless liquid. 1H NMR (500 MHz, CDCl3): delta 8.29 (s, 1H), 7.82 (d, J=8.5 Hz, 2H), 7.34 (d, J=8.5 Hz, 2H), 7.20-7.16 (m, 1H), 5.20 (s, 2H), 2.45 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1065267-14-2, its application will become more common.

Reference:
Patent; Viamet Pharmaceuticals, Inc.; US2012/329788; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 130658-65-0 ,Some common heterocyclic compound, 130658-65-0, molecular formula is C10H14N2O, 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.

The 3-[1-(4-pyridyl)piperidin-4-yloxy]aniline used as a starting material was prepared as follows:- Diethyl azodicarboxylate (3 ml) was added over 15 minutes to a stirred mixture of 1-(4-pyridyl)piperidin-4-ol (3.39 g), 3-(N-tert-butoxycarbonylamino)phenol (Chemical Abstracts, vol. 119, abstract 139113; PCT Patent Application WO 9306085; 3.98 g), triphenylphosphine (4.99 g) and THF (150 ml) which had been cooled to 4 C. The resultant mixture was stirred for 48 hours at ambient temperature. The solvent was evaporated and the residue was purified by column chromatography using a 9:1 mixture of methylene chloride and methanol as eluent. The resultant foam was crystallized from diethyl ether to give tert-butyl N-{3-[1-(4-pyridyl)piperidin-4-yloxy]phenyl}carbamate (4.65 g), m.p. 165-166 C. A 2.2M solution of hydrogen chloride in methanol (45 ml) was added over 15 minutes to a stirred solution in methanol (25 ml) of a portion (2.53 g) of the carbamate so obtained. The mixture was stirred at ambient temperature for 24 hours. The solvent was evaporated and the residue was dissolved in water (50 ml). A 1M aqueous sodium hydroxide solution (25 ml) was added and the mixture was stirred for 1 hour. The precipitate was collected, washed with water and with diethyl ether and dried. There was thus obtained 3-[1-(4-pyridyl)piperidin-4-yloxy]aniline (1.71 g), m.p. 184-186 C.; NMR Spectrum 1.60 (m, 2H), 1.96 (m, 2H), 3.23 (m, 2H+H2O), 3.65 (m, 2H) 4.48 (m, 1H), 5.00 (s, 2H), 6.16 (m, 3H), 6.82 (d, 2H), 6.88 (t, 1H), 8.15 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,130658-65-0, its application will become more common.

Reference:
Patent; ZENECA LIMITED; US2003/207882; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17880-61-4, 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 17880-61-4, name is Methyl 5-ethynylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Sodium 5-[4′-(4′-aminophenyl)buta-1 ‘,3’-diyn-1 -yl]pyridine-2-carboxylate (144): Copper (II) acetate (1 .36 g, 7.46 mmol, 2.0 equiv) is added at room temperature under stream of argon to a stirred solution of 142 (0.60 g, 3.73 mmol) and 4- ethylnylbenzenamine (2.18 g 18.63 mmol, 5.0 equiv) dissolved in anhydrous pyridine (10 mL) and MeOH (10 mL). The reaction mixture is stirred at room temperature for 20 h. The resulting suspension is filtered, and the solid is washed with EtOAc (3^50 mL). The solid is dried under high vacuum for 12 h to afford as an orange powder, and then used for next step directly. 4N NaOH (10 mL) is added to a stirred solution of the crude methyl ester (600 mg) in MeOH (50 mL) at room temperature. Then reaction solution is heated to reflux for 40 min under argon. The reaction mixture turned clear. After all the starting material has been consumed monitored by TLC,the reaction mixture is cooled to room temperature, and the solvents are removed by evaporation under reduced pressure. The yellow solid is washed by water (3^50 mL), EtOAc (3×50 mL) to give a yellow solid (320 mg, 31 % yield, for two steps ), which is used for next step without future purification. 1 H NMR (300 MHz, CD3OD) 56.62 (d, J=8.4 Hz, 2H), 7.26 (d, J=8.7 Hz, 2H), 7.59 (d, J=9.0 Hz, 1 H), 8.27 (d, J=10.2 Hz, 1 H), 9.01 (s, 1 H); 13C NMR (75 MHz, CD3OD) 570.50, 75.996, 78.48, 85.59, 107.59, 1 14.17, 127.44, 133.09, 134.06, 137.62, 142.94, 150.69, 170.58; MS (ESI, positive): m/z 263 [M+H+].

According to the analysis of related databases, 17880-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DUKE UNIVERSITY; ZHOU, Pei; TOONE, Eric, J.; WO2012/31298; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6000-50-6, 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 6000-50-6, name is 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6-(4-aminophenyl)-4-{1-[(4-methylphenyl)sulfonyl]-1H-indol-5-yl}pyridazin- 3(2H)-one (200 mg, 0.438 mmol) in dichloromethane (16.2 mL) and N,N-dimethylformamide (4.00 mL) was added pyridine (71.0 muL, 0.876 mmol) followed by portion wise addition of 4- nitrophenyl carbonochloridate (106 mg, 0.526 mmol) over 1 minute, and the reaction mixture stirred at r.t. for1 hour. To this reaction mixture was added N,N-diisopropylethylamine (381 muL, 2.19 mmol) followed by 2,3-dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride (169 mg, 0.876 mmol) under argon and the reaction mixture stirred at r.t. for 16 hours. The reaction mixture was combined with another batch (0.219 mmol), and concentrated to give a residue. The crude residue was triturated with water-ethanol and the resulting precipitate collected by filtration, washed with ethyl acetate, diethyl ether and dried to give 246 mg (90% purity,63% combined yield over two steps) of the desired product as pale yellow solid. (0981) LC-MS (Method 5): Rt = 0.85 min; MS (ESIpos): m/z = 603 [M+H]+ (0982) 1H-NMR (400 MHz, DMSO-D6) delta (ppm): 2.29 (s, 3H), 4.80 (d, 4H), 6.90 (s, 1H), 7.37 (d, 2H), 7.53-7.54 (m, 1H), 7.60-7.66 (m, 2H), 7.83-7.97 (m, 5H), 8.10 (s, 2H), 8.24 (s, 1H), 8.53- 8.55 (m, 1H), 8.63-8.65 (m, 2H).

According to the analysis of related databases, 6000-50-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BOeHNKE, Niels; BERGER, Markus; SOMMER, Anette; HAMMER, Stefanie; FERNANDEZ-MONTALVAN, Ernesto, Amaury; STELTEN-LUDWIG, Beatrix; GUeNTHER, Judith; MAHLERT, Christoph; GREVEN, Simone; SARKER, Abul, Basher; TAIT, Michael; (451 pag.)WO2019/149637; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 829-45-8, Methyl 3-(4-Pyridyl)-3-oxopropanoate, 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, HPLC of Formula: C9H9NO3, blongs to pyridine-derivatives compound. HPLC of Formula: C9H9NO3

General procedure: A solution of the amidine 6 (1.1 equiv, 276 mg, 1.23 mmol) and the beta-ketoester 8a (1 equiv, 200 mg, 1.12 mmol) in nBuOH (3 mL) was stirred at 110 C for 18 h. During this time a solid precipitate formed. After cooling to room temperature, the solid was filtered off and air-dried to provide 9a (190 mg, 48%) as a pale yellow solid;

At the same time, in my other blogs, there are other synthetic methods of this type of compound,829-45-8, Methyl 3-(4-Pyridyl)-3-oxopropanoate, and friends who are interested can also refer to it.

Reference:
Article; Large, Jonathan M.; Torr, Jane E.; Raynaud, Florence I.; Clarke, Paul A.; Hayes, Angela; Stefano, Francesca Di; Urban, Frederique; Shuttleworth, Stephen J.; Saghir, Nahid; Sheldrake, Peter; Workman, Paul; McDonald, Edward; Bioorganic and Medicinal Chemistry; vol. 19; 2; (2011); p. 836 – 851;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem