Month: April 2022

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.785762-99-4, name is 2-(5-(Trifluoromethyl)pyridin-2-yl)acetic acid, molecular formula is C8H6F3NO2, molecular weight is 205.134, as common compound, the synthetic route is as follows.category: pyridine-derivatives

(6) To a 250 ml single-mouth bottle, 15.8 g (0.282 mol, 1.0 eq) of potassium hydroxide was added.Water 54 ml (1 v / w), stir and dissolve. Compound 785762-99-4 54g (0.282 mol, 1.0 eq) was added to the system and stirred to dissolve. After stirring at 40 C for 1 h, the reaction solution was concentrated. A pale yellow solid powder of 61 g was obtained in a yield of 89%. The nuclear magnetic data is as follows:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,785762-99-4, 2-(5-(Trifluoromethyl)pyridin-2-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Chen Min; (6 pag.)CN108997202; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 722550-01-8, name is 4-(Pyrrolidin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C9H13N3

General procedure: Compound 2-(4,5-dichloro-2-methoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 88 was prepared in the same manner as 2-(5-chloro-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 5a. The resulting hydrobromic acid salt was neutralized with dilute aqueous ammonia to obtain free base and as an off-white solid (48 rng, 72%). 1H NMR (400 MHz, CDC13): delta 8.48 (s. 1H), 7.87 (s, 1H), 7.85 (d, J = 7.6 Hz, 1H), 7.02 (s, 1H ), 6.42 (br s, 1H), 6,36 (dd, 1H, J= 2.4 Hz, 7.5), 3.97 (s, 3H), 3,38-3.33 (m, 4H), 2.07-2.03 (m, 4H); HPLC (Method 1) 99,73% (AUC), tR = 1 1,76 min.; APCI MS m/z 362 [ M + H ]+

With the rapid development of chemical substances, we look forward to future research findings about 722550-01-8.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 84487-15-0, Adding some certain compound to certain chemical reactions, such as: 84487-15-0, name is 2-Bromo-5-nitropyridin-4-amine,molecular formula is C5H4BrN3O2, 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 84487-15-0.

A solution of 2-bromo-5-nitropyridin-4-amine (1.5 g, 6.9 mmol) in acetic acid (20 mL) was added in portions into a 75 C suspension of iron powder (1.5 g, 27 mmol) in acetic acid (20 mL). The reaction mixture was stirred at 75 C for 2 h, cooled to room temperature, and filtered through celite. To the filtrate was added 1,3-bis(methoxycarbonyl)-2-methyl-2- thiopseudourea (1.4 g, 6.9 mmol), and the mixture was stirred at 65 C for 60 h. The reaction mixture was cooled to room temperature and concentrated. The solid residue was triturated with dichloromethane and dried to give the title Compound (1.8 g, quantitative yield) as an orange solid. MS (EI) for C8H7BrN4O2: 271/273 (MH+).

According to the analysis of related databases, 84487-15-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; ANAND, Neel, Kumar; BLAZEY, Charles, M.; BOWLES, Owen, Joseph; BUHR, Chris, Allen; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen; JOSHI, Anagha; KIM, Angie, Inyoung; TSUHAKI, Amy, Lew; MA, Sunghoon; MANALO, Jean-claire, Limun; NG, Stephanie; PETO, Csaba, J.; RICE Kenneth D.; TSANG, Tsze, H.; ZAHARIA, Cristiana, A.; WO2010/135524; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 39891-09-3, Adding some certain compound to certain chemical reactions, such as: 39891-09-3, name is 2-Chloropyridine-5-acetonitrile,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 39891-09-3.

22.0 g (144 mmol) of (6-chloropyridin-3-yl)acetonitrile are added to a mixture of 270 ml of ethanol and 101 ml conc. sulfuric acid, and the mixture is stirred under reflux for 24 h. With stirring, the reaction mixture is then slowly added dropwise to a mixture of 350 g of sodium bicarbonate and 1 liter of water. The aqueous phase is extracted with dichloromethane (five times 400 ml each). The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent using a rotary evaporator. This gives 23.1 g (80% of theory) of the title compound, which is reacted without further purification.1H-NMR (400 MHz, DMSO-d6): delta=8.32 (d, 1H), 7.78 (dd, 1H), 7.49 (d, 1H), 4.10 (q, 2H), 3.77 (s, 2H), 1.19 (t, 3H).LC-MS (Method 3): Rt=1.91 min; MS (ESIpos): m/z=200 [M+H]+.

According to the analysis of related databases, 39891-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thede, Kai; Flamme, Ingo; Oehme, Felix; Ergueden, Jens-Kerim; Stoll, Friederike; Schuhmacher, Joachim; Wild, Hanno; Kolkhof, Peter; Beck, Hartmut; Akbaba, Metin; Jeske, Mario; US2012/264704; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1060814-91-6 ,Some common heterocyclic compound, 1060814-91-6, molecular formula is C9H10BrNO2, 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 ethyl 2-(4-bromopyridin-2-yl)acetate (1.72 g, 7.05 mmol) in THF (23.49 ml) was added dropwise LDA(4.05 ml, 8.10 mmol, 2M solution in THF) and the resulting mixture was stirred for 40 mm at-78C. Allyl bromide (0.610 ml, 7.05 mmol) was added dropwise, and the stirring was continuedat -78C for 2h and checked by LCMS (little desired product). The reaction mixture was slowly warmed to RT and stirred at RT for lhr (the reaction complete). The reaction was quenched by adding a saturated aqueous solution of NH4C1 (20 mL). The aqueous layer was extracted with Et20 (2 x 20 mL), the organic phases were combined, washed with HC1 (1 M, 20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by flash column chromatography on silica gel (1/1 EtOAc/Hex) to give the titlecompound. LC/MS = 285.77 [M+lj

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. 1060814-91-6, Ethyl 2-(4-bromopyridin-2-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; LIM, Yeon-Hee; XU, Jiayi; ZHOU, Wei; (123 pag.)WO2017/74833; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 92276-38-5, Adding some certain compound to certain chemical reactions, such as: 92276-38-5, name is 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine,molecular formula is C5H3BrN4, 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 92276-38-5.

General procedure: To a stirred solution of 6-bromo-1H-i,2,3-triazolo[4,5-b]pyridine (250 mg, 1.26 mmol) in DMF (5 mL) at rt was added 60% sodium hydride in mineral oil (55 mg, 1.38 mmol) and the mixture was stirred at rt for 30 mins. (2-(Chloromethoxy)ethyl)trimethylsilane (419 mg, 2.51 mmol) was added and the mixture was stirred for 15 h. The reaction mixture was partitioned between water and EtOAc and the aqueous layer was separated and further extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0 – 20% EtOAc in hexanes to afford a 1:1 mixture of 6-bromo- 1 -((2- (trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5-b]pyridine and 6-bromo-3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo[4,5 -b]pyridine (240 mg) as an oil, which was not purified further. LC-MS (ESI) mlz 329 and 331 (M+H).v [000223] Step 2: A 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 40%) was obtained as a solid using a procedure analogous to that described in Step 3 of Example4, substituting the product obtained from Step 1 of this example for the 2-chloro-6,7- dimethoxyquinoxaline used in Example 4 and substituting 2-(4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (Ref: S. Abraham et al, WO 2011022473 Al) for the 2-(2-fluoro-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1 -(trifluoromethyl)cyclopropyl)isoxazol-3 -yl)acetamide used in Example 4. LC-MS (ESI) mlz 561 (M+H).[000224] Step 3: To a 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 0.127 mmol) was added trifluoroacetic acid (5 mL), and the mixture was stirred at rt for 1 h. The mixture was concentrated under reduced pressure and the residue was purified by reverse-phase preparative HPLC using a mixture of water (containing 5% CH3CN and 0.05% HCOOH) and CH3CN (containing 0.05% HCOOH) as the mobile phase and Varian Pursuit XRs diphenyl column as the stationary phase to afford 2-(4-(3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)phenyl)-N- (5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (12 mg, 22%) as a solid. ?H NMR (500 MHz, DMSO-d6) oe 11.41 (br s, 1H), 9.00 (d, J= 2.0 Hz, 1H), 8.60 (br s, 1H), 7.80 (d, J 8.5 Hz, 2H), 7.48 (d,J 8.5 Hz, 2H), 6.95 (s, 1H), 3.77 (s, 2H), 1.53 (s, 6H); LC-MS (ESI) m/z 431 (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. 92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HOLLADAY, Mark, W.; LIU, Gang; ROWBOTTOM, Martin, W.; WO2015/31613; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18699-87-1, 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. 18699-87-1, name is 2-Methyl-3-nitropyridine, 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.

Example 1; Scheme A; A mixture of a-1 (0.0072 mol) and paraformaldehyde (0.0058 mol) in DMSO (3.5ml) and triton B (0.27ml) was stirred at 90C for 4 hours, then cooled to room temperature and purified by column chromatography over silica gel (eluent: CH2CI2 then CH2CI2/ CH3OH/NH4OH (99/1/0.1); 15mum). The pure fractions were collected and the solvent was evaporated, yielding: 0.3 g of intermediate a-2 (20%).

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 18699-87-1, 2-Methyl-3-nitropyridine.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/136562; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1448427-99-3, Adding some certain compound to certain chemical reactions, such as: 1448427-99-3, name is 6-(4-Isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-amine,molecular formula is C10H13N5, 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 1448427-99-3.

5-(4-Cyclopropyl-1H-imidazol-1-yl)-2-fluoro-4-methylbenzoic acid hydrochloride (30 g,102 mmol) was suspended in anhydrous 1,2-dichioromethane (900 mL) at room temperature. Oxalyl chloride (18 ml, 205 mmol) was added while stirring under nitrogen, followed by N,N25 dimethylformamide (0.783 ml, 10.2 mmol). The mixture was stirred for about 4 hr at roomtemperature, and then the solvent was removed under reduced pressure. The residue was dissolved in about 600 mL anhydrous dichloromethane. 6-(4-Isopropyl-4H-1,2,4-triazol-3- yl)pyridin-2-amine (22.9 g, 113 mmol) and 4-dimethylaminopyridine (12.5g, 102 mmol) were rapidly added with stirring under nitrogen. The reaction was stirred for about 2 hours at roomtemperature and the dichioromethane was evaporated. The residue was dissolved in 500 mL water and solid NaHCO3 was added until the pH of the mixture was about 7. DichiOromethane was added (about 500 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2 x 300 mL). The combined organics were washed with water (2 x 200 mL),dried over MgSO4, filtered and concentrated. The residue was dissolved in a minimum amount of THF, and water was added slowly until a thick slurry was formed. The solids were collected by filtration, washed with water, and dried.The solids obtained (about 72 g) were recrystallized from hot EtOH (Smug solid) and the solids collected by filtration, washed with 2:1 diethyl ether/EtOH, followed by diethyl ether and dried

According to the analysis of related databases, 1448427-99-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; ANDRES, Mark; CARRA, Ernest, A.; CHAN, Brenda, J. Burke; CHIU, Anna; LAPINA, Olga, Viktorovna; LATHROP, Stephen, P.; SMOLENSKAYA, Valeriya; YU, Lok, Him; (187 pag.)WO2016/105453; (2016); 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. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-2-chloro-6-picoline

Example 633-[4-Chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-6-methyl-2-pyridinecarboxylic acidCla)2-Chloro-5-(2-chloro-6-methyl-3-pyridinyl)-JV-(tricyclo[3.3.1.13’7]dec-l-ylmethyl)-benzamideA mixture of [4-chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-boronic acid (Example 2 (a)) (174 mg), 3-bromo-2-chloro-6-methyl-pyridine (104 mg),potassium carbonate (138 mg) and Z?w(triphenylphosphine)palladium(II) chloride (27 mg)in tetrahydrofuran (2 mL) and water (2 mL) was stirred at room temperature under anitrogen atmosphere over 72 hours. The mixture was filtered through diatomaceous earth,washing with methanol, and the filtrate was concentrated in vacuo. Purification bychromatography (SiOa, zsohexane:emyl acetate 1:1 as eluant) gave the sub-title compoundas a solid (135 mg).MS: APCI(+ve) 429/431 (M+H*)

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, 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; ASTRAZENECA AB; WO2006/25783; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 3430-21-5, 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 3430-21-5 as follows.

Step-I: 6-Amino-5-methyl-pyridine-3-carbonitrile To a mixture of DMF:water (100:2, 102 mL) was added 5-bromo-3-methyl-pyridin-2-amine (10 g, 53.47 mmol), zinc cyanide (3.77 g, 32.1 mmol) and 1,1′-Bis(diphenylphosphino)ferrocene (3.56 g, 6.4 mmol) and degassed for 20 mins. To this was added tris(dibenzylideneacetone)dipalladium (0) (2.45 g, 2.67 mmol) and heated at 120 C. After stirring for 16 h, reaction mixture was cooled to room temperature. To it was added mixture of saturated solution of ammonium chloride: ammonium hydroxide:water (4:1:4, 100 mL). Slurry formed was cooled to 0 C. and again mixture of saturated solution of ammonium chloride: ammonium hydroxide:water (4:1:4, 100 mL) added and stirred for 1 h. Solid formed was filtered through Buchner funnel and dried under high vacuum to get 6.0 g (81%) of titled compound as a tan solid. MS (ES) m/z 134.1 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3430-21-5, its application will become more common.

Reference:
Patent; Kharul, Rajendra; Bhuniya, Debnath; Mookhtiar, Kasim A.; Singh, Umesh; Hazare, Atul; Patil, Satish; Datrange, Laxmikant; Thakkar, Mahesh; US2015/65464; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem