Month: August 2021

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4152-92-5, name is (2-(Aminomethyl)phenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Formula: C8H11NO

[00177] Compound 24: An ice-cold pyridine solution (10 mL) of compound 23 (1 mmol) is treated successively, in a dropwise fashion with acetyl choride (1 mmol), then after 5 min with MsCl (1.1 mmol). The solution is warmed to room temperature then the solvent is removed. The residue is dissolved in EtOAc, washed with water, dried (MgS04), filtered and reduced in vacuo. Purification by column chromatography affords pure compound 24.

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, 4152-92-5, (2-(Aminomethyl)phenyl)methanol.

Reference:
Patent; ONTORII, INC.; VERDINE, Gregory, L.; MEENA, Meena; IWANOTO, Naoki; BUTLER, David, Charles Donnell; WO2013/12758; (2013); 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. 171011-37-3, name is (4-Bromo-1,2-phenylene)dimethanol, molecular formula is C8H9BrO2, 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. name: (4-Bromo-1,2-phenylene)dimethanol

To a solution of (COCl)2 (2.6 equiv.) in anhydrous DCM (1.4 mL per mmol of diol) was added dropwise a solution of anhydrous DMSO (5.2 equiv.) in anhydrous DCM (2.2 mL per mmol of diol) at -78 C and under a nitrogen atmosphere. After 10 min stirring at -78 C, a solution of diol (1.0 equiv.) in anhydrous DCM (2.2 mL per mmol of diol) was added at this temperature. The reaction mixture was stirred at -78 C for 1h under a nitrogen atmosphere before Et3N (1.4 mL per mmol of diol) was added dropwise. The reaction mixture was warmed to rt and stirred for 2-18 h under a nitrogen atmosphere. The reaction was then quenched by addition of H2O. The organics were extracted with DCM, combined, washed with water, washed with brine, dried over MgSO4 and concentrated in vacuo to afford the desired o-phthaldialdehyde.

With the rapid development of chemical substances, we look forward to future research findings about 171011-37-3.

Reference:
Article; D’Hollander, Agathe C.A.; Westwood, Nicholas J.; Tetrahedron; vol. 74; 2; (2018); p. 224 – 239;,
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Synthetic Route of 702-98-7 ,Some common heterocyclic compound, 702-98-7, molecular formula is C11H18O, 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.

EXAMPLE 77 4-(2-Methyl-2-adamantyloxy)-nitrobenzene To 13.8 g. (0.0830 mole) of 2-methyl-2-adamantanol stirred in a mixture of 80 ml. of benzene and 40 ml. of DMF was added in portions 4.18 g. (0.087 mole of NaH) of 50% NaH in oil. Heating was commenced and when vigorous gas evolution was evident, the heat was lowered. When the reaction subsided, the mixture was refluxed for 20 minutes. To this mixture, cooled almost to room temperature, was added 11.7 g. (0.0830 mole) of p-fluoronitrobenzene, and the mixture was refluxed for 6 hours. The mixture was allowed to cool. Water and CH2 Cl2 were added. The CH2 Cl2 layer was washed with two 250 ml. portions of water, which were extracted with 100 ml. of CH2 Cl2. The combined CH2 Cl2 solutions were dried over anhydrous MgSO4 and concentrated The crude product was chromatographed on 700 g. of silica gel, eluding with 1:1 Skellysolve B:CH2 Cl2, to give 17.0 g. of product. Anal. Calcd for C17 H21 NO3: C, 71.06; H, 7.37; N, 4.87; O, 16.70. Found: C, 71.19; H, 7.48; N, 5.12.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,702-98-7, its application will become more common.

Reference:
Patent; The Upjohn Company; US4036977; (1977); A;,
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Synthetic Route of 50739-76-9, 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. 50739-76-9, name is (2-Amino-3,5-dibromophenyl)methanol, molecular formula is C7H7Br2NO, 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.

Adding 4.84kg of N-methylcyclohexylamine and 0.44kg of toluene to a 30L glass reactor with a water separator5.0 kg of 3,5-dibromo-2-aminobenzyl alcohol, 0.5 kg of solid super acid SiO2-OSO3H (SSA), 1.2 kg of acetic acid, and then heated to 85 C for a total of 12 hours after stirring.Sampling UPLC test (take the reaction solution as a sample at a concentration of approximately 275 mg/ml).After passing the reaction (3,5-dibromo-2-aminobenzyl alcohol is not more than 5.0%), it is concentrated under reduced pressure until no significant fraction is distilled off, and the residue is transferred to a barrel and cooled to room temperature, and then 12 kg of acetone is added.The solution was then transferred to a 100 L double-layer glass reactor and adjusted to pH 2 – 3 with 15% hydrochloric acid to precipitate a solid. After 20 minutes,Repeat the measurement of pH 2 ~ 3; continue to stir for 1 hour, then continue to cool to 0 C for 4 hours, centrifugal filtration, to obtain bromohexine hydrochloride wet,The wet product is placed in a blast drying oven tray, dried at 35±5C, and turned once every 3 hours.After drying for 10 hours, 6.24 kg was obtained after the water was qualified, and the yield was 85%. Bromohexidine hydrochloride refined: Adding 42.0 kg of 95% ethanol and 6.2 kg of crude bromohexidine hydrochloride to a 100 L enamel reactor.The temperature was raised to reflux, stirred and dissolved, and then 0.15 kg of activated carbon was added, and the mixture was decolorized by stirring for 1 hour.The titanium rod was filtered, and the filtrate was transferred to a 100 L double-layer glass reactor and slowly cooled to room temperature.Then, the crystallized mixture was stirred at room temperature for 2 hours, and then cooled to 5 C and stirred for 5 hours.The mixture was filtered by centrifugation, and the filter cake was rinsed with a small amount of 95% ethanol to obtain bromohexine hydrochloride wet product.The bromohexine hydrochloride wet product is placed in a vacuum drying oven tray and dried at 60 C, and the degree of vacuum is less than -0.08 mPa.The material was turned over once every 2 hours, dried for 12 hours, and the water was qualified to receive 4.96 kg, and the yield was 80%.

According to the analysis of related databases, 50739-76-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Yipinhong Pharmaceutical Co., Ltd.; Guangdong Zerui Pharmaceutical Co., Ltd.; Li Hanxiong; Lan Xiaobing; Yan Xinxing; (20 pag.)CN109535010; (2019); A;,
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Application of 3973-18-0, 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 3973-18-0, name is Propynol ethoxylate. This compound has unique chemical properties. The synthetic route is as follows.

4-((2-azidoethyl)amino)-N-(2-fluorophenyl)-N’-hydroxy-1,2,5-oxadiazole-3-carboxamidine (III-3, 0.75g, 2.45mmol) into a 50mL eggplant-shaped bottle,Add 2mL of water and 12mL of acetonitrile solution respectively. Under ice bath, add ethoxylated propynol (290 muL, 2.94 mmol) and cuprous iodide (93 mg, 0.49 mmol), and keep stirring for 0.5 h.Then transfer to room temperature and continue to stir the reaction for about 8h,TLC monitored the reaction until the reaction was complete (developing agent: dichloromethane: methanol = 15:1 v/v); the solvent was distilled off under reduced pressure, methanol (20 mL) was added and stirred for 30 min, filtered with suction, and the solvent was distilled off under reduced pressure to obtain a light brown solid , Column chromatography purification (eluent: petroleum ether: ethyl acetate = 2:1 ~ 1:4v/v), to obtain 275mg white solid I-6, the yield was 27.6%,

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 3973-18-0, Propynol ethoxylate.

Reference:
Patent; China Pharmaceutical University; Zhu Qihua; Zhang Shan; He Guangchao; Shen Hui; Wang Yiwei; Gu Shuhui; Sun Zeren; Xu Yungen; (24 pag.)CN111138425; (2020); A;,
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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.403-41-8, name is 1-(4-Fluorophenyl)ethyl Alcohol, molecular formula is C8H9FO, molecular weight is 140.16, as common compound, the synthetic route is as follows.Computed Properties of C8H9FO

General procedure: To a mixture of 1,3-dicarbonyl compound (2 mmol),alcohol or styrene derivatives (1 mmol), and 0.6 gSBNPSA, was added 2 cm3 nitromethane as solvent. Themixture was stirred under reflux conditions and the reactionwas followed by TLC. After completion, the mixture wasfiltered, and the remaining was washed with warm ethanolto separate catalyst and nitromethane was removed underreduced pressure. Then, the crude products were recrystallizedfrom mixture of dichloromethane and n-hexane.All the synthesized products were known and characterized by comparison of their spectral and physical data withthose reported in literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,403-41-8, 1-(4-Fluorophenyl)ethyl Alcohol, and friends who are interested can also refer to it.

Reference:
Article; Karimzadeh, Morteza; Saberi Asl, Hamed; Hashemi, Hajar; Saberi, Dariush; Niknam, Khodabakhsh; Monatshefte fur Chemie; vol. 149; 12; (2018); p. 2237 – 2244;,
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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. 110-73-6, name is 2-(Ethylamino)ethanol, the common compound, a new synthetic route is introduced below. name: 2-(Ethylamino)ethanol

A mixture of 1-(6-hydroxy-2-naphthyl)ethanone (744 mg, 3.92 mmol), sodium hydrogen sulfate(IV) (1.66 g, 16 mmol), 2-ethylaminoethanol (2 mL) and water (5 mL) was heated in a steel bomb at 130-140 C. for 3 days. After cooling, the mixture was distributed between water and ethyl acetate, and the organic layer was washed with brine, dried and evaporated. The residue was dissolved in acetone and loaded onto a 4 mm dry silica plate for radial chromatography. The plate was eluted with a 1:1 mixture of petroleum ether and ethyl acetate. Appropriate fractions were collected and evaporated to give 125 mg (12%)of 1-{6-[ethyl-(2-hydroxylethyl)-amino]-2-naphthyl}ethanone.

The synthetic route of 110-73-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the Univ. of California; US6274119; (2001); B1;,
Alcohol – Wikipedia,
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Reference of 2077-19-2, 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.2077-19-2, name is 2-(4-Bromophenyl)propan-2-ol, molecular formula is C9H11BrO, molecular weight is 215.09, as common compound, the synthetic route is as follows.

General procedure: General Procedure C: To vial equipped with a stir bar and placed under argon atmosphere was added N- ((S)-l-(3-(4-chloro-l-methyl-3-(methylsulfonamido)-lH-indazol-7-yl)-4-oxo-7-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydroquinazolin-2-yl)-2-(3,5- difluorophenyl)ethyl)-2-((3bS,4aR)-3-(difluoromethyl)-5,5-difluoro-3b,4,4a,5-tetrahydro- lH-cyclopropa[3,4]cyclopenta[l,2-c]pyrazol-l-yl)acetamide (1 equiv, typically 25-50 mg), the appropriate aryl halide/heteroaryl halide (3 equiv), potassium acetate (2.6 equiv) and Pd(PPh3)4 (0.2 equiv). The vial was sealed with a septum capped. To the vial was added l,4-dioxane:water (4: 1) to afford a reaction volume 0.05M in boronic ester. The reaction solution was degassed with argon. The reaction mixture was stirred at 90 C for 5h or l6h. Upon cooling to ambient temperature, the reaction mixture was concentrated in vacuo and the resulting residue was subjected to HPLC purification to afford the indicated product. Alternately, (S)-2-(3-cyclopropyl-lH-pyrazol-l-yl)-N-(2-(3,5-difluorophenyl)-l-(3-(4- (morpholinosulfonyl)phenyl)-4-oxo-7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4- dihydroquinazolin-2-yl)ethyl)acetamide or 2-((3bR,4aS)-3-(difluoromethyl)-5,5-difluoro- 3b,4,4a,5-tetrahydro-lH-cyclopropa[3,4]cyclopenta[l,2-c]pyrazol-l-yl)-N-((S)-2-(3,5- difluorophenyl)- 1 -(3 -(4-(morpholinosulfonyl)phenyl)-4-oxo-7 -(4,4,5,5 -tetramethyl- 1,3,2- dioxaborolan-2-yl)-3,4-dihydroquinazolin-2-yl)ethyl)acetamide may be substituted for N- ((S)-l-(3-(4-chloro-l-methyl-3-(methylsulfonamido)-lH-indazol-7-yl)-4-oxo-7-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydroquinazolin-2-yl)-2-(3,5- difluorophenyl)ethyl)-2-((3bS,4aR)-3-(difluoromethyl)-5,5-difluoro-3b,4,4a,5-tetrahydro- lH-cyclopropa[3,4]cyclopenta[l,2-c]pyrazol-l-yl)acetamide. Example 18: Preparation of N-((S)-l-(3-(4-chloro-l-methyl-3-(methylsulfonamido)-lH- indazol-7-yl)-7-(4-(2-hydroxypropan-2-yl)phenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-2- (3,5-difhiorophenyl)ethyl)-2-((3bS,4aR)-3-(difluoromethyl)-5,5-difluoro-3b,4,4a,5- tetrahydro- lH-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol- 1 -yl)acetamide The title compound was prepared according to General Procedure C using 2-(4- bromophenyl)propan-2-ol as the coupling partner. Specific details are provided as a representative example of this general procedure. To a 1 dram vial equipped with a stir bar was added N-((S)- 1 -(3 -(4-chloro- 1 -methyl-3 -(methylsulfonamido)- lH-indazol-7 -yl)-4- oxo-7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydroquinazolin-2-yl)-2-(3,5- difhiorophenyl)ethyl)-2-((3bS,4aR)-3-(difluoromethyl)-5,5-difhioro-3b,4,4a,5-tetrahydro- lH-cyclopropa[3,4]cyclopenta[l,2-c]pyrazol-l-yl)acetamide (40 mg, 0.043 mmol), 2-(4- bromophenyl)propan-2-ol (27.7 mg, 0.129 mmol), potassium acetate (10.96 mg, 0.112 mmol) and Pd(Ph3P)4 (9.93 mg, 8.59 pmol). The vial was capped with a septum cap and then placed under argon atmosphere (vac/fill x 3). To the vial was added dioxane (687 pl) and water (172 m). The reaction mixture was degassed (vac/fill with argon x 3, the solvent boils slightly under brief vacuum). The reaction mixture was stirred at 90 C for 5 hr. Upon cooling to room temperature, the contents of the vial were transferred to a 20 mL scintillation vial with the aid of DCM and then was concentrated in vacuo using a Biotage V10 evaporator. The residue was then taken up in DMF (1.5 mL) and then filtered through a syringe filter. The filtrate was subjected to HPLC purification with the following conditions: Column = Zorbax Eclipse Plus C 18, 21.2 x 100 mm, 5 pm particles; Solvent A = 0.1% Formic Acid in 100% Water. Solvent B = Acetonitrile. Flow Rate = 40 mL/min. Start % B = 53.2 Final % B = 73.2. Gradient Time = 7 min, then a 2 min hold at 98% B. Wavelength = 215 and 254 nm. ESI+ Range: 150 to 1500 dalton. Sample was loaded at 30% B. This purification afforded N-((S)-l-(3-(4-chloro-l-methyl-3-(methylsulfonamido)- lH-indazol-7-yl)-7-(4-(2-hydroxypropan-2-yl)phenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)- 2-(3,5-difluorophenyl)ethyl)-2-((3bS,4aR)-3-(difluoromethyl)-5,5-difluoro-3b,4,4a,5- tetrahydro-lH-cyclopropa[3,4]cyclopenta[l,2-c]pyrazol-l-yl)acetamide (9.9 mg, 25 % yield, 100% purity). The sample was analyzed using LCMS Method D: retention time = 2.45 min.; observed ion = 939.2 (M+H). 1H NMR (METHANOL-d4, 500 MHz) d 8.35 (d,1H, J=7.9 Hz), 8.13 (s, 1H), 7.96 (br d, 1H, J=8.2 Hz), 7.81 (br d, 2H, J=7.9 Hz), 7.71 (d, 2H, J=8.2 Hz), 7.31 (br d, 1H, J=7.6 Hz), 7.20 (d, 1H, J=7.6 Hz), 6.8-6.8 (m, 1H), 6.63 (br d, 2H, J=6.7 Hz), 4.9-4.9 (m, 1H), 4.55 (d, 2H, J=4.0 Hz), 3.63 (s, 3H), 3.5-3.5 (m, 1H),3.4-3.4 (m, 1H), 3.2-3.3 (m, 3H), 3.12 (br dd, 1H, J=9.2, 14.0 Hz), 2.4-2.5 (m, 2H), 1.63 (s, 6H), 1.36 (br d, 1H, J=6. l Hz), 1.01 (br s, 1H)

Statistics shows that 2077-19-2 is playing an increasingly important role. we look forward to future research findings about 2-(4-Bromophenyl)propan-2-ol.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BENDER, John A.; FRENNESSON, David B.; GILLIS, Eric P; IWUAGWU, Christiana; KADOW, John F; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M.; RAJAMANI, Ramkumar; SAULNIER, Mark G.; WANG, Alan Xiangdong; (313 pag.)WO2019/198024; (2019); A1;,
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Synthetic Route of 534-03-2, 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. 534-03-2, name is 2-Aminopropane-1,3-diol. A new synthetic method of this compound is introduced below.

Preparation of the compound of formula (III) starting from the isolated compound (II), in the presence of calcium hydroxide. Calcium hydroxide (12.8 g, 0.173 mol) was slowly added, under stirring and keeping the temperature below 25C, to a solution of compound (II) (120 g, 0.169 mol) in 305 g of DMA.Further on, to the reaction mixture a solution of 2-amino-l,3-propandiol in DMA (133 g, 28% w/w, 0.406 mol) was added dropwise in a period of time of about 45 minutes. The mixture was kept at about 300C for 10 hours, up to the completion of the reaction. The crude reaction material containing the derivative of formula (III) may be purified and hydro lyzed according to the procedure of the Example 3 below. HPLC profile of the mixture after treatment of the sample with NaOH: Iopamidol (IV): 97.9%; F-impurity: 0.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,534-03-2, 2-Aminopropane-1,3-diol, and friends who are interested can also refer to it.

Reference:
Patent; BRACCO IMAGING SpA; CERAGIOLI, Silvia; CIARCIELLO, Giovanni; INCANDELA, Salvatore; MINOTTI, Pietro; WO2010/57765; (2010); A1;,
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