Tag: M.W:100-200

Application of 121643-44-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 121643-44-5 as follows.

Intermediate 1 : 5-Bromo-2-methoxy-3-trifluoromethyl-pyridine To 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 1 13.0 mmol) and 1 ,3-dibromo-5,5- dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18h under argon. The TFA was removed in vacuo (50 mbar, 45C) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL).The filtrate was concentrated in vacuo, diluted with heptane/ tert-butyl methyl ether (5/1 , 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane / EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHC03 (20g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5g, 74% yield). 1 H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,121643-44-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo; GRAVELEAU, Nadege; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STOWASSER, Frank; STRANG, Ross; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2012/4299; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100155-73-5 , The common heterocyclic compound, 100155-73-5, name is 1-(2-Pyridyl)-1-propylamine, molecular formula is C8H12N2, 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 8 mL vial charged with imidazole (17.3 mg, 0.26 mmol) and tert-butyl (6-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)(ethyl)carbamate (26.5 mg, 0.051 mmol) in DCM (1ml) was added 1,1′-carbonyldiimidazole (25 mg, 0.153 mmol). The reaction mixture was stirred at room temperature for 5 h, leading to a clear yellow solution. A solution of 1-(pyridin-2-yl)propan-1-amine, 2HCl (21.33 mg, 0.102 mmol) and DIEA (0.045 ml, 0.255mmol) in DMF (1 ml) was added. The vial was capped and the contents stirred at room temperature for 16 h. The reaction mixture was concentrated and the resulting residue redissolved in TFA (1 ml) and stirred at room temperature for 20 minutes. Triethylsilane (0.008 ml, 0.051 mmol) was added dropwise, and the reaction mixture stirred for an additional 5 minutes. The mixture was concentrated, re-dissolved in DMSO (1.5 mL) and submitted for purification by mass-triggered preparative HPLC to afford 1-(3-(ethylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-(pyridin-2-yl)propyl)urea (4.1 mg, 0.012 mmol, 23.69 % yield) as a white solid.

The synthetic route of 100155-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WILSON, Kevin, J.; WITTER, David, J.; SILIPHAIVANH, Phieng; LIPFORD, Kathryn; SLOMAN, David; FALCONE, Danielle; O’BOYLE, Brendan; MANSOOR, Umar Faruk; LIM, Jongwon; METHOT, Joey, L.; BOYCE, Christopher; CHEN, Lei; DANIELS, Matthew, H.; FEVRIER, Salem; HUANG, Xianhai; KURUKULASURIYA, Ravi; TONG, Ling; ZHOU, Wei; KOZLOWSKI, Joseph; MALETIC, Milana, M.; SHINKRE, Bidhan, A.; THATAI, Jayanth Thiruvellore; BAKSHI, Raman Kumar; KARUNAKARAN, Ganesh Babu; WO2014/52563; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6938-06-3, 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 6938-06-3, name is Butyl nicotinate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The obtained compounds II was dissolved with ethanol (90 mL) and hydrazine hydrate (85percent, 30 mL),then the mixture was heated to reflux for 6 h. After the reaction was completed, ethanol and the excess of hydrazine hydrate were distilled out under a reduced pressure, and a white product was left. The crude product was recrystallized from ethanol to afford white crystals III.

According to the analysis of related databases, 6938-06-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Ning; Sheng, Jun-Feng; Song, Fei; Tong, Yu-Zhu; Wang, Zuo-Xiang; Russian Journal of General Chemistry; vol. 85; 3; (2015); p. 746 – 751;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 956010-87-0 ,Some common heterocyclic compound, 956010-87-0, molecular formula is C7H4F3N3, 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.

A mixture of compound 12 (50 mg, 0.27 mmol), benzylbromide (50 mg, 0.29 mmol) and caesium carbonate (104 mg, 0.32 mmol) was stirred overnight at room temperature in DMF (1.0 mL). It was then diluted with tert-butyl methyl ether and washed with water. The organic layer was dried over sodium sulfate and the solvent was evaporated. The crude product was purified by column chromatography (eluent: cyclohexane/ethyl acetate 3:1) to yield 50 mg (67 %) of the title compound. 1H NMR (400 MHz, DMSO-d6): delta 5.82 (s, 2H), 7.26-7.37 (m, 5H), 7.50 (dd, J=8.2, 4.5Hz, 1H), 8.39 (d, J=8.2Hz, 1H), 8.79 (dd, J=4.5, 1.2Hz, 1H). 13C NMR (125 MHz, DMSO-d6): delta 50.8, 111.4 (q, 1JC,F=1.4Hz), 119.7, 121.4 (q, 1JC,F=269Hz), 127.7, 127.9, 128.7, 129.3, 131.5 (q, 2JC,F=38.6 Hz), 136.2, 149.8, 151.0. HRMS m/z calcd for C14H10F3N3: 277.0827; found: 277.0825.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,956010-87-0, its application will become more common.

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

Adding a certain compound to certain chemical reactions, such as: 73455-13-7, 4,5-Dichloropicolinic 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, Formula: C6H3Cl2NO2, blongs to pyridine-derivatives compound. Formula: C6H3Cl2NO2

A mixture of HATU (155 mg, 0.41 mmol), 4,5-dichloropicolinic acid (39 mg, 0.20 mmol) and (S)-2-(methoxymethyl)pyrrolidine (117 mg, 1.02 mmol) was stirred at 25C for 16h. The crude reaction mixture was directly purified by preparative HPLC (15 min gradient of 60:40 to 0:100 hhOMeOH (both modified with 0.1 % formic acid); flow rate 20 mLmin 1) affording the title compound (39 g, 66%) as a colourless oil that existed as a mixture of rotamers. Rotamer . 1 H NMR (500 MHz, Methanol-d4) d 8.71 (s, 1 H), 7.96 (s, 1 H), 4.44- 4.38 (m, 1 H), 3.82-3.75 (m, 1 H), 3.68-3.64 (m, 2 H), 3.40 (s, 3 H), 2.14-1.96 (m, 5 H). Rotamer B : 1 H NMR (500 MHz, Methanol-d4) d 8.69 (s, 1 H), 7.95 (s, 1 H), 4.85-4.78 (m, 1 H), 3.75-3.69 (m, 1 H), 3.63-3.58 (m, 2 H), 3.17 (s, 3 H), 2.14-1.96 (m, 4 H), 1.94-1.80 (m, 1 H). LCMS (Method T2) Rt = 1.39 min; m/z 289.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73455-13-7, 4,5-Dichloropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; BELLENIE, Benjamin Richard; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; HUCKVALE, Rosemary; COLLIE, Gavin; MENICONI, Mirco; BRENNAN, Alfie; LLOYD, Matthew Garth; (222 pag.)WO2019/197842; (2019); 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.188577-68-6, name is 4,5-Dichloropyridin-2-amine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.name: 4,5-Dichloropyridin-2-amine

Description 77: 2,4,5-trichloropyridine (D77); 4,5-dichloro-2-pyridinamine D76 (360 mg) was dissolved in HCl (8 ml, 96 mmol) at O0C, then sodium nitrite (305 mg, 4.42 mmol) was added portionwise, and the resulting yellow mixture was stirred at 0 0C for 1 hour and then at room temperature for 1 hour. On the basis of HPLC/MS, starting material was consumed to give the required product and the corresponding pyridone.The reaction was then poured into ammonium hydroxide (10 ml) in ice and extracted with Et2O (3×150 ml). The collected organic phases were dried over Na2SO4, then filtered and carefully concentrated (max 200 mBar) to give the title compound D77 (200 mg) as yellow oil.UPLC (Acid GEN_QC_SS): rt = 0.86 minutes, peak observed: 184 (M+2) C5H2Cl3N requires 182.1H NMR (400 MHz, CHLOROFORM- d) delta ppm 7.48 (s, 1 H) 8.43 (s, 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,188577-68-6, 4,5-Dichloropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); 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. 90610-06-3, name is Methyl 2-(6-methylpyridin-3-yl)acetate, molecular formula is C9H11NO2, 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. Application In Synthesis of Methyl 2-(6-methylpyridin-3-yl)acetate

To a stirred solution of methyl (6-methylpyridin-3-yl)acetate (60 mg, 0.36 mmol) in methanol (5 ml) was added NaOH (1.0 ml of a 2M aqueous solution, 2.0 mmol) and the resulting solution was heated at 65 0C for 2 hours. The solvent was then removed at reduced pressure and the resulting residue was dissolved in methanolic HCl (5 ml) and then reconcentrated to yield the title product (54 mg, quant, yield) that was used without further purification. LCMS data: Calculated MH+ (152); Found 100% (MH+) m/z 152, Rt = 0.79 min. Method C.

With the rapid development of chemical substances, we look forward to future research findings about 90610-06-3.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; DAVENPORT, Adam, James; HALLETT, David, James; STIMSON, Christopher, Charles; WO2010/86403; (2010); A1;,
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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid, the common compound, a new synthetic route is introduced below. Formula: C7H6N2O4

REFERENTIAL EXAMPLE 3 Synthesis of N,N-diethyl 2-methyl-5-nitronicotinamide (No. 98) In dry chloroform were dissolved 0.3 g of 2-methyl-5-nitronicotinic acid and 1.5 ml of diethylamine. After addition of 10 g of phosphorous pentaoxide, the mixture was stirred with heating at 55 – 60 C. for 3 hours. After cooling, the chloroform portion was separated and evaporated under reduced pressure. The residue was, after addition of water, neutralized with sodium hydrogen carbonate and extracted with ethyl acetate. The extract was concentrated and purified on a silica gel column to give 0.25 g of a colorless oil. Analysis for C11 H15 N3 O3:

The synthetic route of 59290-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company Limited; US4053608; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 695-98-7, 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. 695-98-7, name is 2,3,5-Trimethylpyridine, molecular formula is C8H11N, 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.

The yield of the product 2,3,5-collidine obtained from 3,5-lutidine used as a starting material was 86percent, and that of 2,3,5,6-tetramethylpyridine obtained therefrom was 3.4percent. The selectivities of the above-mentioned products were 96.3percent and 3.7percent, respectively.

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 695-98-7, 2,3,5-Trimethylpyridine.

Reference:
Patent; Koei Chemical Co., Ltd.; US4658032; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63237-88-7, 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 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Pyrazolo[1,5-a]pyridine-2-carboxylic acid (J. Het. Chem., 18(6), 1981, 1149-1152, at page 1152) (81.8 mg, 0.50 mmol) was dissolved in 1-methyl-2-pyrrolidinone (3 mL) and the solution treated with 1-hydroxybenzotriazole hydrate (74.3 mg, 0.55 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (115 mg, 0.60 mmol) and the mixture stirred at room temperature for 5 minutes. The mixture was then treated with the amine of preparation 18 (200 mg, 0.48 mmol) and N-ethyldiisopropylamine (155 mg, 1.20 mmol) and the reaction mixture stirred at room temperature for 48 hours. The reaction mixture was partitioned between ethyl acetate (75 mL) and water (75 mL) and the organic layer washed with water (3*50 mL) and 0.880 ammonia in water (100 mL), dried over magnesium sulphate and concentrated in vacuo. The residue was triturated with ether to yield the title product as a white solid, 223 mg. 1H-NMR(DMSO-D6, 400 MHz): 1.70(m, 8H), 2.41(s, 3H), 3.87(m, 1H), 3.98(m, 1H), 6.94(m, 2H), 7.00(m, 1H), 7.07(m, 2H), 7.38(m, 2H), 7.65(d, 1H), 7.74(m, 1H), 8.00(m, 1H), 8.22(m, 2H), 8.62(m, 1H). MS ES+ m/z 542 [MNa]+

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2005/20626; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem