Day: September 29, 2021

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. 5407-87-4, name is 2-Amino-4,6-dimethylpyridine. A new synthetic method of this compound is introduced below., name: 2-Amino-4,6-dimethylpyridine

to a 100 mL 3 -necked round-bottom flask was placed 4,6-dimethylpyridin-2-amine (1.0 equiv, 19.6 mmol, 2.4 g) and DCM (20 mL). The reaction system was cooled down to -50 C in a liquid nitrogen bath, and l,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (1.0 equiv, 19.6 mmol, 5.6 g) was added. The resulting solution was stirred at -50 C for 30 min and gradually warmed to 25 C in 30 min. The reaction mixture was quenched with saturated NaHCO, (20 mL) and extracted withdichloromethane (2 x 20 mL). The organic layers were combined and concentrated under vacuum to afford 3.2 g (81.0%) of 5-bromo-4,6-dimethylpyridin-2-amine as an off-white solid. (M+H)+= 200.8, 202.8

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, 5407-87-4, 2-Amino-4,6-dimethylpyridine.

Reference:
Patent; CRINETICS PHARMACEUTICALS, INC.; ZHAO, Jian; WANG, Shimiao; ZHU, Yunfei; (212 pag.)WO2019/157458; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131747-61-0, 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. 131747-61-0, name is (2-(Trifluoromethyl)pyridin-4-yl)methanol. A new synthetic method of this compound is introduced below.

To a mixture of (2- (trifluoromethyl) pyridin-4-yl) methanol A-2 (400 mg, 2 mmol) in dichloromethane (5mL) was added SOCl2(2mL) slowly at 0 . The reaction mixture wa stirred at 60 for 1 h. The reaction mixture was then quenched with 1 mL saturated aqueous NH4Cl and extracted with ethyl acetate (5mL × 3) . The combined organic extracts were concentrated in vacuo, the residue was purified on silica gel (EtOAc: petroleum ether 1: 5) to give the product as a solid (300 mg, 60 ) MS (ESI) calc?dfor (C7H5ClF3N) [M+H]+: 195.0 found: 195

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131747-61-0, (2-(Trifluoromethyl)pyridin-4-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ARASAPPAN, Ashok; BUNGARD, Christopher James; FRIE, Jessica L.; HAN, Yongxin; HOYT, Scott B.; MANLEY, Peter J.; MEISSNER, Robert S.; PERKINS, James; SEBHAT, Iyassu K.; WILKENING, Robert R.; (140 pag.)WO2016/29454; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13534-97-9, 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.13534-97-9, name is 6-Bromopyridin-3-amine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.

Example 1; 6-Bromo-3-pyridnoI.; 3-Amino-6-bromopyridinc (1.73 g, 10 mmol) was dissolved in HBF4 (5 mL, 50 % aq.) and water (5 mL) was added. To the resulting brownish solution, cooled to O0C in an ice-bath, NaNO2 (759 mg, 11 mmol) in water (5 mL) was added dropwisc. The resulting yellowish heterogenous reaction mixture was stirred for 1 h at this temperature. After addition of water (5 mL), the mixture was stirred in an oil -bath for 5 h at 1000C (gas evolution). The cooled reaction mixture was then neutralized by addition OfNaHCO3 (5 % aq.) and the product extracted with ethyl acetate (5 x 35 mL). After drying (NaiSO4) and evaporation in vacuo, the resulting brownish solid was purified by column chromatography (SiO2) using pentane/ethyl acetate (9:1) to give 1.04 g (60 %) of the title compound, mp 137-1380C (lit. 135.5-136.5 0C; den Hertog et al Rec. Tray. Chim. Pays-Bas 1959, 69, 1281).

The chemical industry reduces the impact on the environment during synthesis 13534-97-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; KAROLINSKA INSTITUTET INNOVATIONS AB; WO2009/144253; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 133081-24-0 ,Some common heterocyclic compound, 133081-24-0, molecular formula is C6H7N3O2, 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.

Water was purified and deionized (18 MOmega/cm2) via a Milli-Q water filtration system (Millipore Corp., Milford, MA). 99Mo-99mTc generators were purchased from TecnoNuclear (Argentina). High performance liquid chromatography (HPLC) was performed on an HPLC Varian 5000 Liquid Chromatograph, integrator 4290 Varian, simultaneous detection by NaI (Tl) crystal detector (ORTEC)) and UV detector (lambda= 254 nm), Column Thermo Scientific Hypersil ODS (C18) (300 mm × 4.6 × 10 mum). The flow rate was 1mL/min used with a gradient mobile phase from 100% of A (0.1% TFA in H2O) to 100% of B (0.1% TFA in acetonitrile) in 20 min. Labeling conditions: 1 mL of HYNIC-hydrazone in DMSO (1mg/mL) was incubated with 0.4 mL of tricine solution (100 mg/mL in water), 0.2 mL nicotinic acid solution (10 mg/ml in water), 100 muL of 99mTcO4- (37-111 MBq) and 15 muL of SnCl2.2H2O (1 mg/mL in nitrogen-purged 0.1 M HCl) for 60 min at 70 oC tofinal pH 5. The reaction was analyzed for radiochemical purity by HPLC. CPS: counts per second.

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. 133081-24-0, 6-Hydrazinylnicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Teixeira, Vania; Cabral, Pablo; Porcal, Williams; Arkivoc; vol. 2018; 5; (2018); p. 29 – 38;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 106877-33-2, name is 5-Amino-2-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. Quality Control of 5-Amino-2-(trifluoromethyl)pyridine

6-trifluoromethyl-pyridin-3-ylamine (0.25 g, 1 .54 mmol) was added to a mixture of sodium hydride (0.22 g, 9.16 mmol) and N,N-dimethylformamide (2 mL) at 25 – 30 C under nitrogen gas and the reaction mixture was stirred for 15 – 20 min. Compound of example 2 (0.44 g, 1 .7 mmol) was added to the reaction mixture and was stirred for 6 – 8 h. The reaction mixture was cooled to 10 C and methanol (1 .2 mL) was added slowly. A solution of chilled 20 % ammonium chloride solution (10 mL) was added drop-wise to the reaction mixture at 10 C and was stirred for 25 – 30 min. The precipitated product was filtered, and was washed with water followed by petroleum ether. The resulting product was dried at 45 – 50 C for 20 – 22 h. Yield: 0.4 g (68.96 %); 1H NMR (300 MHz, DMSO-d6): delta 10.28 (s, 1 H), 8.9 (s, 1 H), 8.8 (s, 1 H), 8.58 (d, 1 H, 8.7 Hz), 7.87 (d, 1 H, 8.7 Hz), 7.66 (d, 1 H, 9 Hz), 7.32 (s, 1 H), 7.1 (d, 1 H, 8.4 Hz), 3.86 (s, 6H, 6.3 Hz); MS (ES+): 377 (M+1 ).

The synthetic route of 106877-33-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SIVAKUMAR, Meenakshi; JOSHI, Kalpana, Sanjay; HARIHARAN, Sivaramakrishnan; BOKKA, Ravishankar; AWARE, Valmik, Sopan; MANOHAR, Sonal; SONAWANE, Vinay; CHENNAMSETTY, Suneelmanoharbabu; KALE, Ganesh; THOMAS, Becky, Mary; TRIVEDI, Jacqueline, Vinodkumar; WO2013/175415; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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