Tag: M.W:200-300

Application of 1018505-59-3 , The common heterocyclic compound, 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, 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 4 – (2 – chloro -3 – fluoro – pyrazine amino) -2 – pyrimidine formic acid (1.35 g 1.2 eq), 5 – (4 – ethyl – piperazine -1 – yl) – piperidine -2 – amino (0.81 g 1 eq) and triethylamine (500 mul) in DMF (15 ml) in, then added HBTU (1.51 g 1.5 eq). The mixture stirring at room temperature to 16 hours, then EtOAc (50 ml) and saturated NaHCO3Solution (15 ml), and for separating each layer of EtOAc (2 × 15 ml) extraction the aqueous layer, the combined organic layer dried (MgSO4), filtering and evaporation to dryness, the residue through the column chromatography purification, and to obtain white solid compound of 1.42 g (yield: 62%).

The synthetic route of 1018505-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Zou Mingming; Hu Xiande; Sui Rongchun; Xu Man; (14 pag.)CN108689997; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886365-06-6, 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 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide: To 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (200 mg, 0.869 mmol) and methylamine (135 mg, 11.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide (130 mg, 65%) as an off-white solid.

According to the analysis of related databases, 886365-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89364-04-5, 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. 89364-04-5, name is 3-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, 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 (0052) Non-radioactive fluorination of 3-bromo-4-nitropyridine (3): 10 muL of 1 M tetrabutylammonium fluoride (TBAF) solution in THF (10 mumol, 0.5 eq.) was added to a solution of 3-bromo-4-nitropyridine (96%, Aurum Pharmatech, LLC) (20 mumol, 1 eq.) in 500 L of anhydrous dimethylsulfoxide (DMSO) in a 2 mL HPLC vial. The reaction was analyzed by HPLC (conditions A). Retention times: 3-bromo-4-nitropyridine (3)=10.83 min, 3-fluoro-4-nitropyridine=8.38, 3-bromo-4-fluoropyridine (6)=11.76 min. Retention times for the product matched within 0.05 min the reference standard. Identity of the product was confirmed by HR-MS (m/z M+ exp.: 174.9423, calc: 174.9433) and 1H, 13C and 19F NMR. Product amount was calculated from the area under the curve of the HPLC UV1 trace using a calibration curve.

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 89364-04-5, 3-Bromo-4-nitropyridine.

Reference:
Patent; The University of Chicago; Brugarolas, Pedro; (35 pag.)US2017/355648; (2017); 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. 1060814-91-6, name is Ethyl 2-(4-bromopyridin-2-yl)acetate. A new synthetic method of this compound is introduced below., Formula: C9H10BrNO2

To a solution of compound 5-7 (2 g, 8.19 mmol, 1 eq) in dimethylformamide (20 mL) was added sodium hydride (819 mg, 20.48 mmol, 60% purity in mineral oil, 2.5 eq) at 0C and the mixture was stirred at 20C for 30 minutes. The mixture was cooled to 0C and then compound 5-8 (1.69 g, 9.01 mmol, 680.02 uL, 1.1 eq) was added. The mixture was stirred at 20C for 1 hour. TLC indicated the starting material was consumed completely and a new spot formed. The mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mLx3). The combined organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford compound 5-9 (1 g, 3.11 mmol, 37.90% yield, 83.88% purity) as yellow oil. LCMS: RT = 0.722 min, purity: 83.88%, m/z 269.9, 271.9 [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, 1060814-91-6, Ethyl 2-(4-bromopyridin-2-yl)acetate.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE, INC.; FUSHIMI, Makoto; SCALTRITI, Maurizio; HELLER, Daniel, Alan; MONTERRUBIO MARTINEZ, Carles; ARRUABARRENA ARISTORENA, Amaia; MEINKE, Peter, T.; FOLEY, Michael, Andrew; ASANO, Yasutomi; ASO, Kazuyoshi; TAKAHAGI, Hiroki; SHAMAY, Yosef; BASELGA TORRES, Jose, Manuel; SASAKI, Yusuke; MICHINO, Mayako; (271 pag.)WO2020/72892; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1147422-00-1 ,Some common heterocyclic compound, 1147422-00-1, molecular formula is C12H22N2O2, 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 tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (0.63 g) in acetone (15 mL) was added K2CO3 (1.54 g) and 1-bromo-3-chloropropane (1.45 mL). The reaction mixture was heated to reflux overnight, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the title compound as pale yellow liquid (0.65 g, 77.00%).

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. 1147422-00-1, tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1052714-48-3 ,Some common heterocyclic compound, 1052714-48-3, molecular formula is C6H3BrFNO2, 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.

Preparation of 6-Bromo-N-(3,5-dichlorophen l)-3-fluorop ridine-2-carboxamide (Exp- 10-g3)[0126] Into a vessel containing 50 mL of dimethylformamide (DMF) was dissolved lg Exp-10-g2 prepared in the previous step (4.55 mmol) and 0.70g of 3,5- dichlorobenzenamine. Into this solution were added 2.76 g HATU (7.27 mmol) and 1.39g triethylamine (TEA, 13.64 mmol). The reaction mixture thus prepared was stirred at RT overnight, then the mixture was poured into cool water and extracted with EtOAc. The combined organics were washed with brine, dried over MgSC>4, filtered, and concentrated under reduced pressure. The crude product thus obtained was purified on silica column chromatogram (PE/EtOAc = 15: 1-1 : 1) to give 1.28 g of Exp-10-g3 (calculated yield 77.5%). The identity of the product was confirmed by mass spectroscopy in accordance with procedures described herein. MS (ESI): m/z 363, 365, 367, 369 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1052714-48-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP; ADDEX PHARMA S.A.; LIVERTON, Nigel; JONES, Philip; BOLEA, Christelle; CELANIRE, Sylvain; TANG, Lam; BOUDOU, Cedric; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/60029; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 57883-25-7, 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 57883-25-7, name is 3-Bromo-2-ethoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-2-ethoxy-pyridine (350 mg, 1 .7 mmol) in NMP (2 ml_) was added Zn(CN)2(244 mg, 2.1 mmol) and Pd(dppf)CI2(127 mg, 0.17 mmol). The mixture was degassed with N2and heated at 140C under microwave irradiation for 1 hour. The mixture was cooled to room temperature and filtered through celite. The filtered cake was washed with ethyl acetate (30 ml_). The filtrate was washed with water (20 ml_chi2) and brine (20 ml_), dried over Na2S04, filtered and concentrated. The residue was purified by flash chromatography on silica gel (0%~20% ethyl acetate in petroleum ether) to give 2- ethoxynicotinonitrile.

According to the analysis of related databases, 57883-25-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (270 pag.)WO2018/7249; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1226878-98-3, Adding some certain compound to certain chemical reactions, such as: 1226878-98-3, name is 2-Chloro-5-iodo-4-methoxypyridine,molecular formula is C6H5ClINO, 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 1226878-98-3.

General procedure: The appropriate 5-iodo-2-chloropyridine Intermediate I-8, or I-9 (1 eq) was dissolved in acetonitrile (7 ml. solvent per 1 mmol of compound). 1 -Methyl-4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (1 eq), tetrakis – (triphenylphosphine)palladium(O) (5 mol%) and sodium carbonate (1 .5 eq) were added and the mixture was heated in a microwave reactor at 100C for 30 minutes (Intermediate I-8) or 15 minutes (Intermediate I-9). The reaction mixture was concentrated in vacuo onto silica gel. Gradient chromatography (1-5% MeOH:CH2CI over 15 column volume and 5-10% over 8 column volume) gave the required 5-substituted product.

According to the analysis of related databases, 1226878-98-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; COLLINS, Ian; LAINCHBURY, Michael; MATTHEWS, Thomas Peter; READER, John Charles; WO2013/68755; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75291-85-9, 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.75291-85-9, name is 5-Bromo-2-chloronicotinamide, molecular formula is C6H4BrClN2O, molecular weight is 235.47, as common compound, the synthetic route is as follows.

B) 2-(4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)nicotinamide, bis(trifluoroacetic acid) salt; 4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine (51.7 mg, 0.21 mmol) and 5-bromo-2-chloronicotinamide (50 mg, 0.21 mmol) were suspended in 3:1 isopropanol-NMP (2.1 mL). 4N HCl in 1,4-dioxane (0.21 mL, 0.84 mmol) was added and the reaction was heated to 100 C. for 240 h. The isopropanol was removed by rotary evaporation and the resulting residue was partitioned between 5% aq. NaHCO3 solution (10 mL) and EtOAc (10 mL). The organic layer was separated and the aqueous layer was extracted EtOAc (2×10 mL). The combined organic layers were washed with 10% LiCl (20 mL), dried (MgSO4) and concentrated. The crude product was purified by preparative (RP) HPLC chromatography (YMC S5 ODS, 30×75 mm, 10 minute gradient from 33% to 90% aqueous methanol with 0.1% TFA, 40 mL/min). The fractions containing the desired product were combined and concentrated to afford the desired product as a tan powder (10.1 mg, >98% HPLC purity). 1H NMR (DMSO-d6) delta 12.00 (s, 1H), 11.38 (s, 1H), 8.44 (s, 1H), 8.44 (dd, 1H, J=23.91, 2.03 Hz), 8.13 (d, 1H, J=5.59 Hz), 8.06 (d, 1H, J=13.23 Hz), 7.92 (s, 1H), 7.42 (s, 1H), 7.29-7.38 (m, 2H), 6.46 (d, 1H, J=5.59 Hz), 6.32 (s, 1H); MS(ESI+) m/z 442.1 (M+H)+.

Statistics shows that 75291-85-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloronicotinamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/78140; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 880870-13-3, Adding some certain compound to certain chemical reactions, such as: 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine,molecular formula is C6H5BrClNO, 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 880870-13-3.

The compound (2.82 g, 12.68 mmol) obtained in Step 8 was dissolved in tetrahydrofuran (10 ml) and, under an argon atmosphere, dichlorobis(triphenylphosphine) palladium(II) (445 mg, 0.63 mmol) and 1 M 3-chloro-2-fluorobenzylzinc bromide tetrahydrofuran solution (17.75 ml, 17.75 mmol) were added dropwise, and the mixture was heated under reflux at 80 C. for 2 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to give the object product as a white solid (2.19 g, yield 60%). 1H NMR(CDCl3 300 MHz) (delta) ppm: 3.86 (3H, s), 3.91 (2H, s), 6.79 (1H, s), 6.94-7.01 (2H, m), 7.23-7.28 (1H, m), 8.03 (1H, s)

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. 880870-13-3, 5-Bromo-2-chloro-4-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Satoh, Motohide; Aramaki, Hisateru; Nakamura, Hiroshi; Inoue, Masafumi; Kawakami, Hiroshi; Shinkai, Hisashi; Matsuzaki, Yuji; Yamataka, Kazunobu; US2006/84665; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem