Tag: M.W:100-200

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 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 3-(Chloromethyl)pyridine hydrochloride

General procedure: DMF (5-10 mL/mmol). K2CO3 (10 equiv) was added and the suspensionstirred for 15 min. Then, 3-(chloromethyl) pyridiniumchloride (1.1 equiv) was added and the reaction mixture was stirredfor 48 h at room temperature. The suspension was diluted withH2O and extracted with EtOAc. The combined organic phases werewashed with H2O and brine, dried over magnesium sulfate and thesolvent was removed in vacuo. The crude products were purifiedby column chromatography [Cyclohexane/EtOAc, 3:1 4.2.2.2 tert-Butyl N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-4-fluorobutanoate (S)-Enantiomer ((S)-14): Yield: 1512 mg (85%), greenish, viscous oil. 1H NMR (300 MHz, CDCl3): delta 1.35 (s, 9H), 1.86 (m, 1H), 2.22 (ddt, 2JH,H = 13.6 Hz, 3JH,H = 9.7 Hz, 3JH,H = 6.0 Hz, 1H), 3.86 (s, 3H), 4.19-4.45 (m, 2H), 4.36 (d, 2JH,H = 16.1 Hz, 1H), 4.49 (dd, 3JH,H = 7.7 Hz, 3JH,H = 6.6 Hz, 1H), 4.69 (d, 2JH,H = 16.2 Hz, 1H), 6.96 (dm, 3JH,H = 8.9 Hz, 2H), 7.25 (dd, 3JH,H = 7.9 Hz, 3JH,H = 4.8 Hz, 1H), 7.77 (dm, 3JH,H = 8.9 Hz, 2H), 7.82 (dm, 3JH,H = 8.4 Hz, 1H), 8.51 (s, 1H), 8.53 (s, 1H) ppm. 13C NMR (75 MHz, CDCl3): delta 27.7 (q), 31.8 (dt, 2JC,F = 20.5 Hz), 47.3 (t), 55.6 (q), 57.0 (dd, 3JC,F = 4.3 Hz), 80.1 (dt, 1JC,F = 166.3 Hz), 82.5 (s), 114.1 (d), 123.4 (d), 129.6 (d), 131.3 (s), 132.9 (s), 136.3 (d), 149.1 (d), 149.4 (d), 163.0 (s), 169.0 (s) ppm. 19F NMR (282 MHz, CDCl3): delta -221.4 (ddt, 2JH,F = 46.9 Hz, 3JH,F = 28.3 Hz, 3JH,F = 22.8 Hz) ppm. HRMS (ESI+): C21H27N2O5S+H+, calcd 439.1703, found: 439.1701; C21H27N2O5S + Na+, calcd 461.1522, found: 461.1526; (C21H27N2O5S)2+H+, calcd 877.3328, found: 877.3320; (C21H27N2O5S)2 + Na+, calcd 899.3147, found: 899.3146. MS (ESI+, daughter ion experiment): m/z (%) 439 (15) [M++H+], 383 (100) [439-C4H8], 171 (5) [C7H7O3S+], 167 (10) [383-C7H7O3S-CO2H], 92 (3) [C6H6N+]. Optical rotation (c 1.001, CHCl3): [alpha]58920 = +34.1, [alpha]57820 = +35.5, [alpha]54620 = +41.1, [alpha]43620 = +74.5, [alpha]36520 = n.d.

With the rapid development of chemical substances, we look forward to future research findings about 6959-48-4.

Reference:
Article; Behrends, Malte; Wagner, Stefan; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Kumbhar, Sadhana; Waller, Mark; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3809 – 3818;,
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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. 113118-81-3, name is 5-Bromonicotinaldehyde, the common compound, a new synthetic route is introduced below. Quality Control of 5-Bromonicotinaldehyde

To a solution of 5-bromonicotinaldehyde (XXXVII) (2.0 g, 10.8 mmol, 1 eq) in MeOH (20 mL) was added NaBH4 (2.4 g, 64.9 mmol, 6 eq) and the reaction mixture was stirred at room temperature for 3 h. The mixture was concentrated in vacuo and the residue was diluted in water (15 mL), the aqueous phase was extracted with DCM (10 mL x 3). The combined organic layers were dried over Mg504, filtered and concentrated in vacuo to afford (5- bromopyridin-3-yl)methanol (XLIV) (1.8 g, 9.57 mmol, 90.0% yield) as a colorless oil. ?H NMR (CDC13, 500 MHz) ppm 4.73 (s, 2H), 7.90 (s, 1H), 8.47 (s, 1H), 8.57 (s, 1H). ESIMS found for C6H6BrNO mlz 188.0 (M+H).

The synthetic route of 113118-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (307 pag.)WO2017/23989; (2017); A1;,
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Reference of 109-04-6, 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 109-04-6 as follows.

To a solution of 2-bromopyridine (XCIII) (10 g, 63 mmol, 1.00 eq) in THF (150 mL) was added n-BuLi (25.3 mL, 63 mmol, 1.00 eq) and the mixture was stirred at -70C for 30 mm under nitrogen atmosphere. Then n-Bu3SnCl (21.7 g, 67 mmol, 1.06 eq) was added and the mixture was stirred at the same temperature for another 2 h. Saturated ammonium chloride solution (150 mL) was added to the solution and extracted with EtOAc (150 mL x 3). The combined organic layers were dried over Na2504, filtered and concentrated in vacuo to afford the crude 2-(tributylstannyl)pyridine (XCIV) (25.9 g, 63 mmol, 100% yield) as a yellow oil. The crude product was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109-04-6, its application will become more common.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (307 pag.)WO2017/23989; (2017); A1;,
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Reference of 1594-57-6 ,Some common heterocyclic compound, 1594-57-6, molecular formula is C6H7N3O, 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.

General procedure: a) To a mixture of the carboxylic acid (5 mmol) in acetone (20 mL) was added EDC (5.5 mmol). The reaction mixture was stirred at room temperature for 30 min, then the amidoxime (5 mmol) was added. The resulting mixture was stirred at room temperature for 12 h. Acetone was evaporated at reduced pressure and to the residue was added water (100 mL). The resulting precipitate was filtered off, washed with water (50 ml) and dried under vacuum at rt.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1594-57-6, its application will become more common.

Reference:
Article; Baykov, Sergey; Sharonova, Tatyana; Osipyan, Angelina; Rozhkov, Sergey; Shetnev, Anton; Smirnov, Alexey; Tetrahedron Letters; vol. 57; 26; (2016); p. 2898 – 2900;,
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Synthetic Route of 55304-73-9, 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. 55304-73-9, name is 2,6-Dichloro-3-formylpyridine. A new synthetic method of this compound is introduced below.

2,6-Dichloronicotinaldehyde (500 mg, 2.84 mmol) was diluted with dimethylamine (3125 muL, 6.25 mmol) and heated to 500C. After stirring for 3 hours, the reaction was loaded onto a silica gel column and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 6-chloro-2-(dimethylamino)nicotinaldehyde (155 mg, 0.840 mmol, 29.6 % yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55304-73-9, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); A1;,
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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. 55240-51-2, name is 2-Phenylisonicotinic acid. A new synthetic method of this compound is introduced below., Safety of 2-Phenylisonicotinic acid

General procedure: To a solution of cyanoacetic acid (340 mg, 4.0 mmol) and 1,1-dioxo-1H-1lambda6-benzo[b]thiophen-6-ylamine (362 mg, 2.0 mmol) in 10 mL of CH2Cl2 was added DIPEA (774 mg, 6.0 mmol). HBTU (1.14 g, 3.0 mmol) was added at 0 C. The resulting mixture was stirred at r.t. for 28 h. The reaction mixture was diluted with CH2Cl2 (80 mL) and washed with water (20 mL). The organic layer was separated and dried with anhydrous Na2SO4. The solution was concentrated to give a crude product, which was purified with silica gel column (EtOAc/hexane = 1/1) to obtain the desired product (400 mg, 81%) as a yellow solid (mp 207-208 C). HPLC purity 98.6% (tR = 10.93 min). 1H NMR (600 MHz, DMSO-d6) delta 10.79 (s, 1H), 8.04 (s, 1H), 7.67-7.69 (m, 1H), 7.60 (d, 1H, J = 7.2 Hz), 7.57 (d, 1H, J = 7.8 Hz), 7.30 (d, 1H, J = 7.2 Hz), 3.98 (s, 2H). 13C NMR (150 MHz, DMSO-d6) delta 162.0, 140.7, 137.3, 132.8, 130.3, 126.7, 126.1, 123.4, 115.6, 111.4, 27.0. HRMS (ESI) calcd for C11H19N2O3S 249.0328 (M + H)+, found 249.0330.

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, 55240-51-2, 2-Phenylisonicotinic acid.

Reference:
Article; Chen, Haijun; Yang, Zhengduo; Ding, Chunyong; Chu, Lili; Zhang, Yusong; Terry, Kristin; Liu, Huiling; Shen, Qiang; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 498 – 507;,
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Adding a certain compound to certain chemical reactions, such as: 97509-75-6, 3-Fluoropicolinonitrile, 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, Product Details of 97509-75-6, blongs to pyridine-derivatives compound. Product Details of 97509-75-6

Pre aration 86A: 3-Fluoro-4-iodopicolinonitrile[00297] To a solution of diisopropylamine (2.80 ml, 19.66 mmol) in THF (Volume: 201 ml) cooled to -78 °C was added n-butyllithium (7.86 ml, 19.66 mmol) dropwise. The dry ice/acetone bath was replaced with an ice water bath and reaction mixture was stirred at 0 °C for 25 min, and then re-cooled to -78 °C. In a separate flask, a solution of 3- fluoropicolinonitrile (1.5 g, 12.29 mmol) in THF (50 mL) was cooled to -78 °C, and then LDA (130 mL, 1.0 equiv) was added. The solution turned dark red. After 35 min, iodine (3.43 g, 13.51 mmol) was added rapidly. The reaction mixture was stirred for 45 min, then quenched with H20. Layers were separated and the aqueous phase extracted with CH2CI2 (2X). Organics combined, dried over Na2S04, filtered, and concentrated to afford a brown residue. The crude material was dissolved in a minimal amount of CH2CI2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (80 g column, 60 mL/min, 0-20percent EtOAc in hexanes over 23 min, tr = 18 min) gave the title compound (1.7 g, 6.79 mmol, 55.2percent yield) as a brown solid.

The synthetic route of 97509-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22282-72-0, 2-Oxo-1,2-dihydropyridine-4-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, Recommanded Product: 22282-72-0, blongs to pyridine-derivatives compound. Recommanded Product: 22282-72-0

Preparative Example 4.30 4-[(4-iodo- lH-pyrazol- 1 -yl)methyl]py Step 1 : Borane-THF (29 mL, 1.0 M) was added to a solution of 2-oxo-l,2- dihydropyridine-4-carboxylic acid (1 g, 7.19 mmol) in THF (15 mL) at 0 C. The mixture was stirred at 25 C for 2 hours. Methanol was added and the mixture was concentrated under reduced pressure to afford 4-(hydroxymethyl)pyridin-2(lH)-one. MS ESI calc’d. for C6H8 02 [M + H]+ 126, found 126. XH NMR (400 MHz, CD3OD) delta 7.40 (d, J= 6.8 Hz, 1H), 6.58 (s, 1H), 6.38 (d, J= 6.4 Hz, 1H), 4.52 (s, 2H).

The synthetic route of 22282-72-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michele, R.; ALTMAN, Michael, D.; ROMEO, Eric, T.; VITHARANA, Dilrukshi; CASH, Brandon; SIU, Tony; ZHOU, Hua; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; HAIDLE, Andrew, M.; CHILDERS, Kaleen Konrad; MADDESS, Matthew, L.; REUTERSHAN, Michael, H.; DUCHARME, Yves; GUERIN, David. J.; SPENCER, Kerrie; BEAULIEU, Christian; TRUONG, Vouy Linh; GUAY, Daniel; NORTHRUP, Alan, B.; TAOKA, Brandon, M.; LIM, Jongwon; FISCHER, Christian; BUTCHER, John, W.; OTTE, Ryan, D.; SUN, Binyuan; WO2013/192125; (2013); A1;,
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Related Products of 18437-58-6 , The common heterocyclic compound, 18437-58-6, name is 4-Amino-2-picoline, molecular formula is C6H8N2, 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.

1003651 Step A: 2-Methylpyridin-4-amine (0.28 g, 2.6 mmol) was placed in THF (5 mL) and cooled to -78C. t-BuLi (1.5 mE, 2.6 mmol) was added dropwise, and the solution was warmed to 0C for 30 minutes. This solution was then added dropwise to a -78C THF solution (5 mL) of (5)-i -(2-(tert-butyldimethylsilyloxy)- 1 -(4-chloro-3 -fluorophenyl)ethyl)-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2( 1 11)-one (0.070 g, 0.13 mmol). The reaction was stirred for an additional 30 minutes at -78C, then poured into water, and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated to give the crude product, which was purified by column chromatography (500:10-500:20 DCM/MeOH) to give the product (5)-i -(2-(tert-butyldimethylsilyloxy)- 1 -(4-chloro-3 – fluorophenyl)ethyl)-4-(2-((2-methylpyridin-4-yl)amino)pyrimidin-4-yl)pyridin-2( 111)-one(0.028 g, 38% yield).

The synthetic route of 18437-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James F.; CHICARELLI, Mark Joseph; GARREY, Rustam Ferdinand; GAUDINO, John; GRINA, Jonas; MORENO, David A.; MOHR, Peter J.; REN, Li; SCHWARZ, Jacob; CHEN, Huifen; ROBARGE, Kirk; ZHOU, Aihe; WO2013/130976; (2013); A1;,
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Reference of 609-70-1, 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.609-70-1, name is 4-Hydroxynicotinic acid, molecular formula is C6H5NO3, molecular weight is 139.11, as common compound, the synthetic route is as follows.

7.92 (1H, d, SPC238 8.57 (1H, s, SPC239 PREPARATION OF THE STARTING MATERIAL To 80 ml. of dichloromethane solution containing 9.8 g. of 4-hydroxynicotinic acid and 10 ml. of triethylamine was added dropwise 7 ml. of thionyl chloride with stirring under ice-cooling over a period of 20 minutes and the mixture was stirred for 2 hours at room temperature. The crystals thus formed were recovered by filtration, washed with a small amount of dichloromethane, and then dried to provide 4-hydroxynicotinoyl chloride.

The chemical industry reduces the impact on the environment during synthesis 609-70-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US3953428; (1976); A;,
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Pyridine | C5H5N – PubChem