Month: March 2021

Synthetic Route of 50595-15-8, 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 50595-15-8, name is tert-Butyl 2-hydroxyacetate. This compound has unique chemical properties. The synthetic route is as follows.

A stirred suspension of 88 mg (2.2 mmol) sodium hydride (60percent dispersion in mineral oil) in 5 ml of dry dimethylformamide at -5¡ã C. under nitrogen was treated with 264 mg (2 mmol) tert-butylglycolate. After 10 minutes 298 mg (2 mmol) of 3,6-dichloropyridazine (Aldrich D7, 320-0) was added and the solution was allowed to warm to room temperature and was stirred overnight. The volatiles were evaporated under reduced pressure and the residue was chromatographed on silica eluding with ethyl acetate/hexane (1:2) to give 210 mg of a gum that was dissolved in 20 ml of ethanol and treated with 10percent palladium on carbon (Fluka) and hydrogenated under a hydrogen atmosphere overnight. The catalyst was removed by filtration and the volatiles were evaporated under reduced pressure to give a gum that was chromatographed on silica eluding with ethyl acetate/hexane (1:2) followed by ethyl acetate to give 50 mg of a gum [M+H+MeCN]+252. The gum was dissolved in 2 ml of dichloromethane and treated with 1 ml of trifluoroacetic acid. After 10 minutes the volatiles were evaporated and the residue triturated with toluene and re-evaportated to give a gum that was further triturated with petroleum ether bp 40-60¡ã C. to give 2-(3-pyrazinyloxy)acetic acid trifluoroacetate.

According to the analysis of related databases, 50595-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US6472404; (2002); B1;,
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Reference of 3840-31-1, 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. 3840-31-1, name is (3,4,5-Trimethoxyphenyl)methanol. A new synthetic method of this compound is introduced below.

General procedure: The compound (3,4,5-trimethoxyphenyl)-methanol 15 (4.5 mmol) was dissolved in THF (15 mL) and added to a stirred suspension of NaH (60%, 5.4 mmol) in THF (5 mL) at 0 C. The reaction mixture was stirred for 30 min at the same temperature. Propargyl bromide (4.9 mmol) was added to the reaction mixture at the same temperature and stirring was continued for an additional 5 h at room temperature. After completion the reaction (TLC), the reaction mixture was quenched with ice water and extract with ethyl acetate (2 * 20 mL). The organic extract was washed with brine, dried over Na2SO4, and solvent removed under reduced pressure. The residue was subjected to silica gel column chromatography purification (ethyl acetate/hexane 1:10) to afford 1,2,3-trimethoxy-5-((prop-2-yn-1-yloxy)methyl)benzene 16.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3840-31-1, (3,4,5-Trimethoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Suman; Murthy, T. Ramalinga; Rajkumar; Srikanth; Dayakar; Kishor, Chandan; Addlagatta, Anthony; Kalivendi, Shasi V.; Raju, B. China; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 603 – 619;,
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Electric Literature of 23147-58-2 , The common heterocyclic compound, 23147-58-2, name is Glycerol aldehyde dimer, molecular formula is C4H8O4, 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.

Step 1: 2-(2-hydroxyethyl)-5-methoxy-1-indanone A solution of 5-methoxy-1-indanone (500 mg, 3.08 mmol) in methanol (10 mL) was treated with 10% palladium on carbon (53 mg) followed by glycoaldehyde dimer (370 mg, 3.08 mmol) and 0.5M sodium methoxide in methanol (1.3 mL, 0.65 mmol). The mixture was placed under a hydrogen atmosphere (balloon) and stirred vigorously at room temperature for 65 hours. After purging with nitrogen, the mixture was filtered through a 0.45 mum Acrodisc and the disk was rinsed with methanol (2 mL). The filtrate was diluted with EtOAc (25 mL), washed with 0.1N HCl (15 mL) and brine (15 mL), dried over MgSO4, filtered, and evaporated under vacuum to a solid. LC-MS of this material showed a mixture of starting material (major) and product. The mixture was purified by chromatography on a Biotage Flash 12M KP-Sil column (12 mm*15 cm). The column was eluted with 3:2 EtOAc-hexanes, collecting 6 mL fractions every 30 sec. Fractions 20-36 were concentrated under vacuum and flashed with benzene to afford 2-(2-hydroxyethyl)-5-methoxy-1-indanone as an oil. 1H NMR (CDCl3, 500 MHz) delta 1.80 and 2.05 (two m, CH2CH2OH), 2.79 and 3.35 (two dd, 3-CH2), 2.83 (m, H-2), 3.77-3.90 (m, CH2CH2OH), 3.87 (s, OCH3), 6.86 (d, H-4), 6.89 (dd, H-6), and 7.67 (d, H-7).

The synthetic route of 23147-58-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wilkening, Robert R.; Fried, Amy; US2006/94779; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2867-59-6, 3-Aminobutan-1-ol, 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, 2867-59-6, blongs to alcohols-buliding-blocks compound. name: 3-Aminobutan-1-ol

A mixture of 2,4-dichloro-6-nitro-quinazoline (80 mg, 0.33 mmol), THF (3.3 mL), 3- aminobutan-1-ol (35 mg, 0.39 mmol) and DIPEA (0.14 mL, 0.82 mmol) was stirred at RT for lh. LCMS (Method T2) Rt = 1.18 mins, mlz 297.08 [M+H]. Acetic acid (4 mL) was added directly to the mixture which was stirred at 70 00 for 16h. LCMS (Method T2) Rt = 0.85 mins, mlz 279.08 [M+H]. The solution was concentrated and the residue was taken up in methanol (5 mL). The solution was then purified using SCX-2 cartridge. The product was eluted with methanolic ammonia, affording 4-[(3-hydroxy-1-methyl-propyl)amino]-6-nitro-1 H-quinazolin-2- one (50 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2867-59-6, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BELLENIE, Benjamin Richard; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; HUCKVALE, Rosemary; LLOYD, Matthew Garth; (360 pag.)WO2018/215798; (2018); A1;,
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Related Products of 4139-61-1, 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.4139-61-1, name is 6-Bromo-4-hydroxycoumarin, molecular formula is C9H5BrO3, molecular weight is 241.04, as common compound, the synthetic route is as follows.

EXAMPLE 50 6-Bromo-4-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-1-benzopyran-2-one 6-Bromo-4-hydroxycoumarin (1.19 mmol, 0.287 g), K2CO3 (3.57 mmol, 0.493 g) and 2-3-(bromopropoxy)tetrahydro-2H-pyran (1.19 mmol, 0.264 g) is suspended in 10 mL of acetone, and is heated to 55 C. for 24 hrs at which time the reaction is not complete. Cs2CO3 (1.54 mmol, 0.5 g) and 5 mL of DMF are added and the reaction is heated for an additional 2 hrs. Twenty-five percent of the crude THP protected material is purified by HPLC to afford the title compound (70.8 mg, 62%); 1H NMR (CDCl3, 300 MHz) delta 7.91 (1H, d, J=2.25 Hz), 7.82 (1H, dd, J=2.5, 9 Hz), 7.39 (1H, d, J=9 Hz), 5.98 (1H, s), 4.59 (1H, m), 4.31 (2H, t, J=6 Hz), 3.83 (1H, m), 3.72 (1H, m), 3.55 (2H, m), 2.09 (2H, m), 1.65 (2H, m), 1.45 (4H, m); MS (ESI, Pos.) calcd for C17H19BrO5 m/z [M+H]=383.0, found 383.1.

The chemical industry reduces the impact on the environment during synthesis 4139-61-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/54681; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14002-80-3, Methyl 3-hydroxy-2,2-dimethylpropanoate, 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, Quality Control of Methyl 3-hydroxy-2,2-dimethylpropanoate, blongs to alcohols-buliding-blocks compound. Quality Control of Methyl 3-hydroxy-2,2-dimethylpropanoate

EXAMPLE 106a Preparation of intermediate 2,2-dimethyl-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester To a mixture of 3-hydroxy-2,2-dimethyl-propionic acid methyl ester (13.2 g, 0.1 mol), K2CO3 (20 g, 0.14 mol) and DMAP (6.2 g, 0.05 mol) in DCM (100 mL) was added p-toluenesulfonyl chloride (19 g, 0.1 mol). The mixture was stirred at room temperature overnight, then filtered. The filtrate was washed with HCl aq. (1 M) and water, dried over anhydrous Na2SO4 and concentrated to give the title compound (15 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14002-80-3, Methyl 3-hydroxy-2,2-dimethylpropanoate, and friends who are interested can also refer to it.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Yang, Song; Zhang, Jing; Zhang, Zhuming; US2009/156610; (2009); A1;,
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Application of 55414-72-7, 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. 55414-72-7, name is (2-Amino-5-methoxyphenyl)methanol, molecular formula is C8H11NO2, 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.

Compound 21 (120 mg, 0.72 mmol) and EDC.HCl (165 mg, 0.86 mmol) were dissolved in DMF(2 mL) and stirred for 5 minutes. To this mixture at 0 C was added a solution of 1-hydroxybenzotriazole (116 mg, 0.86 mmol) and compound 4 (132 mg, 0.86 mmol) in DMF (1mL),followed by DIPEA (0.18 mL, 1.08 mmol). The reaction mixture was stirred under N2 atmosphere atroom temperature for 24 h. The solvent was evaporated under reduced pressure. The crude product was dissolved in HCl (5 mL, 1N) and ethyl acetate (10 mL). After partitioning of the two layers, the aqueous layer was extracted with ethyl acetate (4 x 15 mL). All organic layers were combined and washed with water (10 x 20 mL). Finally the organic layer was dried with MgSO4 and evaporated onto silica. The crude product was purified by column chromatography, eluting with 1:4 ethylacetate/dichloromethane, to produce the title compound as a moist white solid (118 mg, 55%) and 23 asa yellow solid (50 mg, 27%). Data for 22: m.p. 144-146 C; IR (neat) vmax (cm-1) 3232, 3071, 2918,2864, 2712, 2450, 2284, 2111, 2069, 1647, 1580, 1521; 1H NMR (400 MHz, CDCl3) delta 8.56 (s, 1H,NH), 8.11 (d, J = 8.1 Hz, ArH3), 7.97 (d, J = 8.7 Hz, ArH6), 7.68 (m, 3H, ArH4, ArH6, ArH5), 6.93(d, J = 8.7 Hz, ArH5), 6.81 (s, 1H, ArH3), 4.74 (s, 2H, CH2), 3.82 (s, 3H, OCH3) 3.96 (s, H, OH);13C{1H} NMR (101 MHz, CDCl3) delta 164.9 (C=O), 157.2 (C4), 146.8 (C2), 134.0 (C4), 133.2 (C1),132.7 (C1), 130.9 (C6), 129.5 (C2), 128.9 (C5), 125.3 (C6), 124.9 (C3), 113.8 (C5), 64.5 (CH2), 55.7(OCH3); HRMS (ESI, +ve) C15H14N2O5Na+ [MNa+] requires m/z 325.0795, found 325.0772. Data for 23: m.p. 135-137 C; IR (neat) vmax (cm-1) 3235, 3069, 2646, 2321, 2103, 1920, 1729, 1655,1523; 1H NMR (400 MHz, CDCl3) delta 8.30 (s, 1H, NH), 8.14 (d, J = 8.2 Hz, ArH), 7.84-7.81 (m, 2H,ArH), 7.75-7.61 (m, 6H, ArH), 7.03-6.98 (m, 2H, ArH), 5.36 (s, 2H, CH2), 3.83 (s, 3H, OCH3);13C{1H} NMR (101 MHz, CDCl3) delta 166.0, 165.7, 157.9, 148.0, 146.5, 134.1, 133.3, 133.0, 132.3, 130.8, 130.3, 129.1, 129.0, 128.8, 127.5, 127.0, 124.8, 124.0, 116.8, 115.9, 65.7, 55.7; HRMS (ESI,+ve) C22H17N3O8Na+ [MNa+] requires m/z 474.0928, found 474.0882.

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 55414-72-7, (2-Amino-5-methoxyphenyl)methanol.

Reference:
Article; Lizarme, Yuvixza; Wangsahardja, Jonatan; Marcolin, Gabriella M.; Morris, Jonathan C.; Jones, Nicole M.; Hunter, Luke; Bioorganic and Medicinal Chemistry; vol. 24; 7; (2016); p. 1480 – 1487;,
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Reference of 83647-43-2 ,Some common heterocyclic compound, 83647-43-2, molecular formula is C8H9BrO, 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 flask charged with (3-bromo-2-methylphenyl)methanol (6.0 g, 30 mmol) was added a 1M TFA solution of Thallium Trifluoroacetate (16.2 g, 29.8 mmol). The mixture was stirred at RT overnight. Analysis by TLC showed no starting material remaining. The solvent was removed under vacuum, and the residue was pumped under high vacuum for 30 min to ensure complete removal of TFA. To the residue was then added Palladium(II) Chloride (529 mg, 2.98 mmol), Lithium Chloride (2.53 g, 59.7 mmol), Magnesium Oxide (2.41 g, 59.7 mmol), and MeOH (150 mL). The reaction was flushed with CO twice, and kept under CO at room temperature. Analysis by LC showed a big product spot within 2 hours. To this solution was added ethyl acetate to precipitate the salts. The black solution was filtered through a CELITE pad, washed with EtOAc, adsorbed onto silica and purified by silica gel chromatography to afford 5-bromo-4- methyl-2-benzofuran-l(3H)-one. -NMR (500 MHz, CDC13) delta ppm 7.71 (d, J= 8.0 Hz, 1H), 7.58 (d, J= 8.0 Hz, 1H), 5.25 (s, 2H), 2.37 (s, 3H).

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. 83647-43-2, (3-Bromo-2-methylphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CATO, Brian; FRIE, Jessica, L.; KIM, Dooseop; PASTERNAK, Alexander; SHI, Zhi-Cai; WO2014/85210; (2014); A1;,
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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. 16545-68-9, name is Cyclopropanol, molecular formula is C3H6O, 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. COA of Formula: C3H6O

A solution of cyclopropanol (0.060 g, 1.03 mmol) in CH2CI2 (2 mL) was cooled to 0 C, treated with K2CO3 (0.43 g, 3.10 mmol) followed by phosgene (20% wt in toluene, 0.54 mL, 1.03 mmol), and stirred vigorously overnight at 0 C to room temperature. Unreacted phosgene was removed by purging the solution with N2 gas (passed through a KOH solution to dry) for 30 min. The reaction mixture was filtered through anhydrous MgS04, and concentrated at 0 C to afford cyclopropyl chloroformate as a colorless oil (~0.3 mL) that was used directly as a toluene solution for the next step (cyclopropyl chloroformate/cyclopropanol = 1:0.19, theoretical concentration = 2.8 M). 1 H NMR (400 MHz, CDCL) d 4.41-3.36 (m, 1 H), 0.98-0.82 (m, 4 H); 13C NMR (100 MHz, CDCL) d 151.3, 56.2, 5.49.

With the rapid development of chemical substances, we look forward to future research findings about 16545-68-9.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; WIPF, Peter; (79 pag.)WO2019/203951; (2019); A1;,
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Synthetic Route of 4728-12-5, 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 4728-12-5 as follows.

To a suspension of sodium hydride (0.41 g, 10.26 mmol, 60percent in mineral oil) in tetrahydrofuran (15 mL), (2,2-dimethyl-1,3-dioxan-5-yl)methanol (1 , 1 g, 6.84 mmol) was added and the reaction mixture was stirred at room temperature for 10 min. Then methyl iodide (1 .27 mL, 20.52 mmol) was added drop wise at room temperature and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was quenched with ice water (15 mL) and extracted with ethyl acetate (2 x 30 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. The crude was purified by silica gel column chromatography using 60percent ethyl acetate in hexane to afford the title compound 5-(methoxymethyl)-2,2-dimethyl-1,3-dioxane (2, 0.65 g, 60percent yield) as a colorless oil. _ NMR (400 MHz, CDCI3) _ (ppm): 3.97-3.93 (m, 2H), 3.76-3.72 (m, 2H), 3.42 (d, J = 6.8 Hz, 2H), 3.34 (s, 3H), 2.00-1 .94 (m, 1H), 1 .42 (s, 3H), 1 .40 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4728-12-5, its application will become more common.

Reference:
Patent; CADENT THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITI, Frank; FANGER, Christopher; XU, Yuelian; (252 pag.)WO2018/119374; (2018); A1;,
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